Illinois: Chicago – Architecture Boat Tour

February 27, 2021
Illinois

🏙️ Chicago From the Water — Why the Boat Tour Won Every Argument

We had fallen properly in love with the Chicago skyline. It had crept up on us, if we’re honest — the sort of thing that happens gradually and then all at once, like realising you’ve been sitting in a draught for an hour. Chicago had somehow managed to muscle its way to the top of our favourite skylines in the world, and almost certainly the top spot in the United States — yes, including New York. Sorry, New York. You had a good run.

Now, Chicago didn’t get this skyline by accident. The city essentially had to burn down first, which is the architectural equivalent of having to completely demolish your kitchen before fitting a decent one. The Great Chicago Fire of 1871 tore through the city over two days in October, killing around 300 people and leaving roughly 100,000 residents homeless. Out of that catastrophe came something rather remarkable: a complete reimagining of what a city could look like. By the 1880s and 1890s, Chicago’s architects — men like William Le Baron Jenney, Louis Sullivan, and Daniel Burnham — were quite literally inventing the skyscraper. The Home Insurance Building, completed in 1885, is generally credited as the world’s first, standing at a then-staggering ten storeys. Chicago had decided, with some determination, to go upwards.

The result, over the following 140-odd years, was the skyline we were now thoroughly besotted with.

🚁 Getting Up High — Or Sensibly Not

There are, of course, various ways to admire all of this. You can go up to the observation decks — the Skydeck at Willis Tower (which most Chicagoans still call the Sears Tower, opened 1973, was the world’s tallest building for a quarter century) or the 360 CHICAGO deck on the John Hancock Center. Some people favour helicopter tours, which I’m sure are very exciting if you enjoy the sensation of being inside a very loud tin of biscuits while travelling at speed. We did not fancy that particularly. I’ve reached the age where “thrilling” and “enjoyable” are not quite the same thing anymore.

🚤 The Chicago Architecture River Cruise — A Very Good Idea Indeed

What we decided to do instead was take a boat tour along the Chicago River, which turned out to be one of the better decisions we had made since leaving home. The river runs right through the heart of downtown, and from the water you get these extraordinary views of the buildings rising up on either side — close enough to actually read the architectural details, far enough back to take in the whole picture. It’s rather like the difference between pressing your nose against a painting and standing three feet away from it.

The Chicago River itself has a peculiar and rather distinguished history. In 1900, in a feat of engineering that still raises eyebrows, the city reversed its flow — permanently — to stop sewage emptying into Lake Michigan and poisoning the drinking water. Chicago was, by that point, used to doing large and improbable things.

The architecture tour boats have been operating since 1969, run originally by the Chicago Architecture Foundation — now the Chicago Architecture Centre — and the guides are genuinely knowledgeable. This was not the sort of tour where someone with a microphone tells you the building is “really tall” and leaves it at that.

From the river, we took in buildings spanning nearly a century and a half of ambition: the Wrigley Building (1924), gleaming white and rather pleased with itself on the north bank; the Tribune Tower (1925), with its Gothic crown and fragments of famous structures from around the world embedded in its base — there’s apparently a piece of the Taj Mahal in there, which feels slightly colonial but is nonetheless impressive; and Marina City (1964), the twin corncob towers that have appeared on approximately one million record covers and postcards since Wilco put them on the front of Yankee Hotel Foxtrot in 2002.

It was, all things considered, a splendid way to spend a couple of hours. Highly recommended — and considerably less alarming than a helicopter.

🚤 Getting On Board — Sun, Sweat, and Skyscrapers

The architectural boat tours ran every hour throughout the summer and lasted roughly ninety minutes — long enough to feel properly informed, short enough that we didn’t need packed lunches. They departed from the dock area near Navy Pier, which itself is worth knowing about: originally built in 1916 as a cargo and passenger facility stretching 3,300 feet into Lake Michigan, it’s now essentially a small city of shops, restaurants, and tourists doing that thing tourists do, which is walk slowly in groups and stop without warning.

Our boat had two options: an open upper deck or a covered lower deck. We chose the top, naturally, because we are optimists and also apparently incapable of learning from experience. It was a hot Chicago summer day — and Chicago in July is not messing about. The city sits on the southwestern tip of Lake Michigan, which does precisely nothing to cool things down. We needed hats, sunscreen applied with the enthusiasm of someone painting a garden fence, and plenty of water. There are refreshments on board should you forget, so all is not lost.

Chicago has been reinventing its skyline with some enthusiasm lately. When the 836-foot One Bennett Park opened in Streeterville, it was the city’s first 800-footer completed in nearly a decade — followed swiftly by the 896-foot NEMA Chicago at the southern edge of Grant Park. Three further towers above 800 feet were under construction, including the rather ambitious 1,198-foot Vista Tower in Lakeshore East.

We were genuinely excited — old favourites and shiny new arrivals alike.

🏢 Trump Tower — The Building’s Better Than The Man

One of the first buildings we came across was Trump Tower Chicago, and look, let’s be honest about this: the structure itself is genuinely impressive. Completed in 2009 and standing 98 storeys tall, it’s the second-tallest building in Chicago and, depending on how you measure these things, somewhere in the top five tallest in the United States. The architects Skidmore, Owings & Merrill — the same firm responsible for Willis Tower — clearly knew what they were doing.

The man whose name is plastered across it in letters roughly the size of a garden shed, however, is another matter entirely. I’ll say no more than this: standing there on the river, gazing up at all that gleaming glass and steel, it was hard not to feel a quiet sadness about the deep and painful divisions that had carved their way through American life during the 45th President’s time in office. A beautiful building. Complicated feelings.

Not all of what we were looking at was glass and steel modernism. Some of these buildings had been standing since our grandparents were young. The New York Life Building and the Tribune Tower both went up in the 1920s, when Chicago was already well into its second act as a city of serious architectural intent. In their day, they were among the largest buildings on earth — proper giants. They still hold their own perfectly well surrounded by their younger, shinier neighbours, which is either reassuring or deeply depressing depending on your age.

By the 1960s, architects and city planners had started to rethink what a skyscraper was actually for. Rather than simply stacking offices on top of more offices, buildings began combining residential and commercial spaces under one roof — effectively creating small vertical cities within the city. It was, in hindsight, an obvious idea that had somehow taken about eighty years to occur to anyone.

The perfect example of this shift stood right in front of us: Marina City, completed in 1967, those two unmistakable circular towers rising from the riverbank like a pair of enormous stone corncobs. Designed by Bertrand Goldberg, the apartments inside are famously curved throughout, containing almost no right angles whatsoever — which must make hanging pictures an absolute nightmare. The lower floors serve as a parking garage for roughly 900 cars, stacked in a continuous spiral ramp.

Eventually, the river forked, and our boat took the left branch past one of Chicago’s old bascule bridges — the kind that splits in the middle and lifts in two halves like a enormous metal sandwich being prised open. Chicago has more moveable bridges than any other city in the world, around 40 of them, which is either impressive or completely unnecessary depending on your outlook. This particular one, we were told, only opens once a year now. Once a year. I’ve had dentist appointments that felt more essential.

We turned around there and motored back a short way along the second spur, drifting past a pleasant mix of older brick warehouses — the remnants of Chicago’s industrial past — alongside rather newer glass and steel neighbours that had clearly arrived with ideas above their station.

As we turned the boat back towards port, there it was. You couldn’t miss it, frankly — the Willis Tower looming over everything like the villain in a film who doesn’t need to say anything because his mere presence says it all.

Most Chicagoans still call it the Sears Tower, and honestly, who can blame them. It was completed in 1973 at 1,450 feet, making it the tallest building in the world — a title it held, with considerable smugness, for 25 years. It remained the tallest building in the entire Western Hemisphere until One World Trade Center finally nudged it aside in 2014. Four decades is a decent innings by anyone’s measure.

What strikes you most, though, is the look of the thing. While everything else along the Chicago skyline is busily being gleaming, reflective and agreeable, Willis Tower stands there in near-total black, topped by two white television masts that from a distance look uncannily like horns. It genuinely has the aesthetic of a supervillain’s headquarters. Brooding, dominant, entirely unbothered by its cheerful neighbours.

We loved it immediately. Some buildings try to fit in. This one never bothered.

Sadly, all good things had to end, and it was time to point ourselves back towards home. The return journey along the river, though, turned out to have one last trick up its sleeve. Buildings that had been quietly hiding behind their larger, showier neighbours on the way out now revealed themselves as we passed from the opposite direction — a reminder that Chicago, even when you’re leaving it, can’t quite resist showing off just a little bit more.

We both have a thing about architecture — old, new, doesn’t much matter — so the boat tour along the Chicago River was always going to be right up our street. And it absolutely delivered.

For roughly an hour and a half, we drifted past 150 years of architectural ambition while a genuinely knowledgeable guide explained what we were looking at and why it mattered. Chicago essentially invented the modern skyscraper, and the buildings lining the river tell that story rather well — from the ornate early steel-frames of the 1890s through the sleek mid-century giants to the glass towers that went up last Tuesday, or so it seemed.

Along the way we also picked up rather a lot about the city’s wider history — colourful doesn’t quite cover it. Chicago has always done things at a scale most cities wouldn’t attempt.

Thoroughly worth the time. No question.

In Summary …

Chicago is a fabulous city with so much to do to suit all tastes
The river tour is the best way to see the impressive skyscrapers. Another way is to go up one of the sky decks and see the city from above. This is especially cool at night.
Speaking of cool – I am sure you know Chicago is freezing cold in the winter. It is not known as the windy city for nothing!

Planning Your Trip

🚢 Chicago Architecture Center River Cruise


📍 Dock Location	112 E. Wacker Drive, southeast corner of Michigan Ave Bridge at Wacker Drive — look for the black awning	🕖 Season	Daily, March – November
🌐 Website	architecture.org/city-tours/river-cruise	📞 Phone	312-922-3432
⏱️ Duration	90 minutes	🗓️ Departures	10:00 AM, 11:00 AM, 12:00 PM, 1:00 PM, 2:00 PM, 3:00 PM & 5:00 PM daily
🚇 CTA ‘L’ Train	State & Lake (Red, Brown, Green, Orange & Purple Lines); or Clark & Lake (Blue Line) — walk east to Michigan Ave, then north to the river	🚌 Bus	CTA routes 134, 135, 136 along Michigan Avenue stop near the dock

🎟️ Ticket Prices

Adult	Child (4–12)	Infant (under 3)	CAC Members
$54–62	$20–30	$24	2-for-1 once per year

ℹ️ All passengers must have a ticket, including infants. Book via Ticketmaster or call the box office. Tickets are non-refundable. Arrive at least 30 minutes before departure. Tours run rain or shine. Discounted parking available at 111 E. Wacker Drive with validation from the ticket office.

Ticket prices are set by the Chicago Architecture Center and First Lady Cruises and are subject to change; confirm current pricing before booking.

Getting to and Around Chicago

✈️ Arriving by Air

Chicago is served by two major international airports. O’Hare International Airport (ORD) is one of the busiest airports in the world, located around 27 kilometres northwest of the city centre, and handles the majority of long-haul and international flights. Chicago Midway Airport (MDW) sits on the southwest side of the city, approximately 12 kilometres from downtown, and is popular with budget carriers.

Both airports are connected to the city centre via the CTA ‘L’ train — the Blue Line from O’Hare runs 24 hours a day, whilst the Orange Line from Midway operates from around 4:00 am to 1:00 am. Journey times are roughly 45 minutes from O’Hare and 25 minutes from Midway. These are by far the most economical options for getting into town.

Taxis and rideshares (Uber and Lyft) are widely available, though expect to pay $50–70 from O’Hare and $25–40 from Midway to downtown. Shared shuttle services such as GO Airport Express also serve most downtown hotels and must be booked in advance. Car hire is available at both airports, though downtown parking is expensive — upwards of $30 per hour in many locations.

🌐 Flights: flychicago.com 🌐 CTA airport trains: transitchicago.com/airports

🚆 Arriving by Train

Chicago’s magnificent Union Station at 225 South Canal Street is the gateway to the city by rail. A stunning 1925 Beaux-Arts landmark, it serves as the Amtrak hub for the entire Midwest and is the terminus for eight long-distance national routes and eight regional corridor routes. Destinations served include New York, Los Angeles, New Orleans, Seattle, San Francisco, and Washington DC, as well as shorter regional routes to cities like Milwaukee, St Louis, Detroit, and Minneapolis.

Union Station is just a short walk or CTA ride from the Loop, making it a convenient arrival point.

🌐 amtrak.com | Station website: chicagounionstation.com

🚌 Arriving by Coach

For budget-conscious travellers, Chicago is well-connected by long-distance coach. Greyhound operates four stations in the greater Chicago area with routes connecting over 100 US cities. Megabus offers low-cost city-to-city services to numerous destinations and is particularly good value when booked early.

🌐 greyhound.com | megabus.com

🚇 The ‘L’ Train — Getting Around the City

The backbone of Chicago’s public transport is the CTA (Chicago Transit Authority) ‘L’ train, one of the oldest and most extensive urban rail networks in the United States. The ‘L’ (short for elevated, though some sections run underground) is cheap, reliable, and one of the best ways to experience the city. Eight colour-coded lines fan out across the city from the central Loop, the famous circuit of elevated track running around downtown.

Base rail fare is $2.75 per ride (as of 2026 fares). For visitors, the best value is an unlimited ride pass, available as a 1-day ($6) or 7-day ($25) option, covering all CTA trains and buses. The 3-day pass has been discontinued. Passes activate on first use and can be loaded onto a Ventra card or added digitally.

🌐 transitchicago.com

🚌 CTA Buses

Over 127 bus routes serve Chicago and 35 surrounding suburbs, making them a comprehensive complement to the ‘L’. Buses run to virtually every neighbourhood and attraction in the city, though newcomers may find the network a little daunting at first. The same Ventra card and passes work across all CTA buses.

🌐 transitchicago.com

💳 The Ventra Card — Your Travel Card

Ventra is Chicago’s unified fare payment system. Visitors can pick up a physical Ventra card at any CTA station vending machine or add a digital version to an iPhone (Apple Wallet) or Android (Google Wallet). Simply tap to pay at bus fare readers and train turnstiles.

As of 2026, CTA fares are:

Single bus ride: $2.50
Single rail ride: $2.75
Single-ride ticket (disposable): $3.50
1-day unlimited pass: $6
7-day unlimited pass: $25
30-day unlimited pass: $85

You can also use a contactless debit or credit card to pay directly, though a pass will save money for most visitors staying more than a day or two.

🌐 ventrachicago.com

🚉 Regional Day Pass — New for 2025

Launched in June 2025, the Regional Day Pass is a brand-new option allowing unlimited travel on CTA, Metra commuter rail, and Pace suburban buses all in a single purchase — the first time the city’s three transit agencies have offered a truly unified fare. It is available exclusively through the Ventra app. Weekend pricing is a flat $9.50, whilst weekday pricing is tiered based on Metra travel zones ($10–$16).

🌐 Download the Ventra app via ventrachicago.com

🚆 Metra — Commuter Rail

Metra is the regional commuter rail network serving the wider Chicago metropolitan area and surrounding suburbs. With 11 lines and over 240 stations, it’s a smart option for day trips beyond the city — popular destinations include the South Shore and the University of Chicago neighbourhood. Fares are calculated by distance using a zone system. Tickets can be bought at Metra vending machines, via the Ventra app, or from conductors on board.

🌐 metrarail.com

🚤 Chicago Water Taxi

For a scenic and traffic-free way to get around, the Chicago Water Taxi runs along the Chicago River connecting Michigan Avenue (near the Magnificent Mile), the West Loop (close to Union Station and the Willis Tower Skydeck), and Chinatown at Ping Tom Park. Each boat has refreshments and restrooms, and bikes and luggage are welcome on board. The service is seasonal, typically running from late spring through to autumn. Tickets can be bought on board, online, or at the docks.

🌐 chicagowatertaxi.com

🚲 Divvy Bikes & Scooters

Chicago is an impressively bike-friendly city with over 450 miles of bike lanes and trails. Divvy, the city-owned bike share scheme operated by Lyft, offers over 17,000 bikes, 1,500 e-scooters, and more than 1,000 docking stations across Chicago and Evanston — making it the largest bike share network by area in North America. Pick up a bike from any docking station and return it to any other. A 24-hour pass is available from station kiosks or the Divvy app. It’s ideal for short hops between attractions, particularly along the scenic Lakefront Trail hugging Lake Michigan.

🌐 divvybikes.com

🚖 Taxis & Rideshares

Taxis are readily available throughout central Chicago and can be hailed on the street downtown. The main operators are Yellow Cab and Checker Cab, reachable on 312-829-4222. Uber and Lyft are widely used and generally the better option in outer neighbourhoods where street taxis are sparse. Rideshare pick-up at O’Hare is from Terminal 2. Expect surge pricing during peak hours and major events.

🚶 Walking

Do not underestimate Chicago on foot. The downtown Loop and many surrounding neighbourhoods — including the Magnificent Mile, River North, Wicker Park, and Lincoln Park — are highly walkable, and the city scores well for pedestrian infrastructure. The Lakefront Trail offers an 18-mile traffic-free path along Lake Michigan, a highlight for any visitor.

🚗 Driving & Parking

Chicago’s grid system makes navigation relatively straightforward, and the city is accessible via several major interstate highways including the I-90, I-94, and I-55. However, parking downtown is expensive and limited — garage rates can reach $30 per hour or more in the most popular areas. For most visitors, a car is unnecessary if you are staying in or around the city centre. An interactive parking map is available at choosechicago.com.

Best Time to Visit Illinois

🌸 Spring (March–May)

Spring in Illinois is a season of tentative warmth and sudden reversals. March can still deliver icy winds and late snowfall, but by April the landscape softens into greens and blossoms. Chicago’s lakefront parks come alive, tulip gardens burst into colour, and the rivers and wetlands of the state’s interior attract migratory birds in spectacular numbers. The Morton Arboretum near Lisle is exceptional in late April and May, when its flowering trees are at peak display.

Temperatures range from around 4°C in early March to a pleasant 18–20°C by late May. Rainfall increases through the season, and thunderstorms become more frequent as spring progresses. Crowds are modest compared to summer, and accommodation prices remain reasonable. The Chicago Marathon ballot opens in spring, and the city’s cultural calendar fills quickly with outdoor events.

What to pack: Layered clothing is essential — a warm mid-layer, a waterproof outer jacket, light jumpers, and comfortable walking shoes with some water resistance. An umbrella or packable rain mac is a must. Include a light scarf and gloves for early spring evenings.

☀️ Summer (June–August)

Summer transforms Illinois into a vibrant, energetic destination. Chicago hums with festivals nearly every weekend — the Taste of Chicago, Chicago Jazz Festival, and Lollapalooza draw enormous crowds. The lakefront becomes a destination in itself, with beaches, cycling paths, and outdoor cinema. Further south, Shawnee National Forest offers hiking through canyons, bluffs, and cypress swamps that feel entirely unlike the Midwest.

Heat can be intense, particularly in July and August, when temperatures regularly reach 30–33°C and humidity pushes the feels-like temperature even higher. Thunderstorms are common in the afternoons. This is the busiest and most expensive period for travel, particularly in Chicago. Book accommodation and popular restaurants well in advance.

What to pack: Lightweight, breathable clothing in natural fabrics, comfortable walking shoes or trainers, a high-factor suncream, sunglasses, and a sun hat. A compact umbrella handles afternoon storms. A light layer for air-conditioned interiors — restaurants, museums, and transit can be heavily cooled.

🍂 Autumn (September–November)

Many seasoned travellers consider autumn the finest season in Illinois. September retains summer’s warmth without its oppressive humidity, and October delivers some of the most spectacular foliage in the Midwest. The forests of southern Illinois, the river bluffs along the Illinois and Mississippi, and the tree-lined streets of towns such as Galena and Geneva put on a rich display of amber, orange, and crimson.

The Chicago Architecture Biennial (held in even-numbered years) and the Chicago International Film Festival make October a particularly rich month culturally. Temperatures fall steadily from around 22°C in September to near freezing by November, and the first frosts typically arrive in late October. Visitor numbers drop from summer peaks, and prices ease accordingly.

What to pack: Warm mid-layers and a proper coat for November, lighter jackets and jumpers for September and October. Sturdy walking shoes or boots for leaf-season trails. A scarf and gloves become essential by late October. Pack layers that can be added or removed during the day as temperatures shift considerably between morning and afternoon.

❄️ Winter (December–February)

Winter in Illinois is not for the faint-hearted, but it rewards those who embrace it. Chicago becomes a genuinely beautiful winter city — the Magnificent Mile glitters with lights, the city’s museums and restaurants are at their most welcoming, and hotel rates drop significantly. The Chicago Riverwalk takes on a different, quieter character. Galena, with its historic architecture and rolling hills, becomes one of the Midwest’s most charming Christmas destinations.

Temperatures in January average around -6°C, with wind chill regularly making it feel far colder along the lakefront — Chicago’s nickname, the Windy City, is well earned in winter. Snowfall is common from December through February, occasionally heavy. That said, the city functions efficiently year-round and the public transit system keeps running regardless of conditions.

What to pack: A heavyweight winter coat, thermal underlayers, a warm hat covering the ears, a substantial scarf, insulated waterproof gloves, and insulated waterproof boots with good grip. Wool socks are advisable. Pack lip balm and hand cream, as the cold and dry air are harsh on skin. Warm layers for indoors, as heated buildings can be very warm.

🗓️ Overall Best Time to Visit

For most visitors, late May and the whole of September represent the sweet spot for an Illinois trip. The weather is agreeable without being extreme, the landscape is either in full bloom or dressed in early autumn colour, and the crowds and prices of peak summer have yet to arrive or have already eased. Those visiting primarily for Chicago’s cultural life will find October exceptionally rewarding, with a full programme of festivals, events, and comfortable temperatures for exploring on foot. Winter offers genuine value and a different kind of beauty, but demands preparation and an acceptance of the cold. Spring, while unpredictable, brings a sense of renewal to the state that is difficult to match at any other time of year.

Vegan Dining In Chicago

🌱 The Chicago Diner

A Chicago institution since 1983, The Chicago Diner is one of the most beloved vegetarian and vegan restaurants in the city — and arguably the most famous. Its motto, “meat free since ’83,” says it all. The menu is a celebration of plant-based comfort food, with standout dishes including the iconic Radical Reuben (made with house-made seitan), vegan milkshakes, loaded hot dogs, poutine, and a full brunch spread. With two locations — one in Lakeview and one in Logan Square — it has a warm, retro diner atmosphere that draws vegans, vegetarians and omnivores alike.

Location: 3411 N. Halsted St., Chicago, IL 60657 (Lakeview) / 2333 N. Milwaukee Ave., Chicago, IL 60647 (Logan Square)
Website: veggiediner.com
Phone: (773) 935-6696 (Lakeview) / (773) 252-3211 ext. 1 (Logan Square)
Opening Hours:
- Lakeview: Mon–Fri 11am–10pm; Sat–Sun 10am–10pm
- Logan Square: Mon–Fri 11am–9pm; Sat–Sun 10am–9pm

🌿 Handlebar

A Wicker Park neighbourhood favourite since 2003, Handlebar is a casual, made-from-scratch vegetarian and vegan restaurant with a full bar and a beloved beer garden. The menu leans into comfort food — think Nashville hot “chicken” made from hen-of-the-woods mushrooms, buffalo seitan wraps, sloppy joe sandwiches, vegan nachos with cashew cheese, and fried pickles. It’s open late most nights, making it a go-to spot for a casual dinner or night out. The place has a lively, unpretentious atmosphere and is popular with cyclists and locals alike.

Location: 2311 W. North Ave., Chicago, IL 60647 (Wicker Park)
Website: handlebarchicago.com
Phone: (773) 384-9546
Opening Hours:
- Mon–Fri: 10am–12am
- Sat–Sun: 9am–12am

☕ Fancy Plants Café

A cosy 100% vegan café nestled in the East Lakeview neighbourhood, Fancy Plants Café was opened by chef Kevin Schuder and quickly became a local gem for plant-based breakfasts and lunches. The café serves Dark Matter and Big Shoulders coffee alongside an ever-changing selection of house-made pastries, seasonal savoury dishes, NY-style bagels with cashew cream cheese and carrot lox, breakfast burritos and grab-and-go items. Gluten-free options are available throughout the menu. It also hosts occasional ticketed dinner events and Saturday prix-fixe evenings.

Location: 613 W. Briar Place, Chicago, IL 60657 (East Lakeview)
Website: fancyplantscatering.com
Phone: (773) 857-1588
Opening Hours:
- Daily: 8am–4pm

🥬 Kale My Name

Opened in 2020 in the Albany Park neighbourhood, Kale My Name has earned national recognition — including VegNews Magazine’s Veggie Award for Best Vegan Casual Restaurant in the Country. The restaurant describes itself as an “International Vegan Restaurant,” with a globe-spanning menu that takes in Mediterranean, Middle Eastern, Asian, Mexican, Colombian, Italian and Balkan cuisines, alongside American comfort classics like vegan burgers, mac and cheese and nachos. Highlights include the buffalo tofu wrap, fried mac-and-cheese balls and oyster mushroom sandwich. It has a full bar and serves weekend brunch. Celebrity Tabitha Brown is a fan and co-owns the Los Angeles sister location.

Location: 3300 W. Montrose Ave., Chicago, IL 60618 (Albany Park)
Website: kalemyname.com
Phone: (872) 208-7125
Opening Hours:
- Daily: 11am–10pm

🌺 PLANTA Queen

Set in the River North neighbourhood, PLANTA Queen is a 100% plant-based restaurant with a stylish, upscale atmosphere inspired by traditional Chinese courtyard architecture. Part of the acclaimed PLANTA group, the Chicago outpost offers an Asian-influenced menu featuring vegan sushi, nigiri, dumplings, wok noodles, handhelds and seasonal bowls, alongside a full bar with craft cocktails. The Bang Bang Broccoli has become something of a cult dish. It is a popular choice for date nights and special occasions, with a private dining room available for events.

Location: 413 N. Clark St., Chicago, IL 60654 (River North)
Website: plantarestaurants.com
Phone: (312) 527-5800
Opening Hours:
- Mon–Thu: 11:30am–10pm
- Fri: 11:30am–11pm
- Sat: 11am–11pm
- Sun: 11am–10pm

🎵 Soul Veg City

One of Chicago’s oldest and most storied vegan restaurants, Soul Veg City (formerly Original Soul Vegetarian) has been serving exclusively plant-based food on the city’s South Side since 1981 — longer than any other vegan establishment in the Chicago area. Located in the Chatham neighbourhood, the restaurant is a beloved community institution offering vegan soul food and American classics: seitan-based dishes, vegan wings, mac and cheese, pizza, smoothies, juices, pastries and ice cream. The recently renovated space includes a new deli counter, expanded menu, outdoor patio and a selfie wall. It is Black-owned and deeply rooted in the local community.

Location: 203 E. 75th St., Chicago, IL 60619 (Chatham/South Side)
Website: soulvegcity.com
Phone: (773) 224-0104
Opening Hours:
- Mon–Fri: 11am–6pm
- Sat–Sun: 10am–6pm

Where to Stay?

Chicago is one of America’s great cities — a place of jaw-dropping architecture, world-class museums, legendary deep-dish pizza, and a lakefront that stretches to the horizon. Choosing the right neighbourhood to base yourself in can make the difference between a merely good trip and an unforgettable one. The city is broadly manageable, and most of its visitor-facing highlights are clustered around the downtown core, making it relatively easy to explore on foot or via the efficient ‘L’ train network. The guide below covers four of the finest areas for tourists, from the iconic city centre to a hip, local neighbourhood beyond the tourist trail.

🔵 1. The Loop

The Loop is Chicago’s beating heart, the historic central business district that takes its name from the elevated railway that has encircled it since the 19th century. For first-time visitors, it is arguably the most logical base in the entire city, placing you within walking distance of many of Chicago’s most celebrated attractions. Millennium Park and its iconic Cloud Gate sculpture — universally known as ‘The Bean’ — are right on your doorstep, as is Grant Park, the vast green space that stretches along the Lake Michigan shoreline. The Art Institute of Chicago, one of the great art museums of the world, sits just blocks away, and the Willis Tower’s Skydeck — once the tallest building in the world — offers unforgettable views across the city and out over the lake. The Loop’s broad boulevards are lined with landmark buildings that serve as an open-air architecture museum, and the Chicago Theatre District puts world-class performance on your doorstep every evening.

Beyond its sightseeing credentials, the Loop is supremely practical as a base. The ‘L’ train stops are immediately outside most hotels, providing rapid access to every other neighbourhood in the city, and multiple bus routes thread through the streets. The Chicago Riverwalk — a beautifully landscaped path flanking the Chicago River — is perfect for an evening stroll, lined with bars and restaurants that capture the city’s sociable spirit. Dining options range from Michelin-starred establishments to casual deep-dish pizza joints, and State Street offers plenty of shopping. Though the Loop has a reputation for emptying out after office hours on weekdays, evenings in the Theatre District and around Millennium Park are lively year-round, and the area feels both safe and well-lit after dark.

🏨 Where to Stay in The Loop

⭐⭐⭐⭐⭐ Upscale — The Langham, Chicago — A superbly located luxury hotel occupying a skyscraper designed by the legendary architect Mies van der Rohe, sitting directly above the Chicago River just two blocks from the Magnificent Mile. The award-winning Chuan Spa, outstanding Travelle restaurant, and elegantly appointed rooms with floor-to-ceiling windows make this one of the finest places to stay in the entire city. Rated 9.4/10 on Booking.com from over 1,000 reviews. 👉 Book on Booking.com
⭐⭐⭐ Mid-Range — Hilton Garden Inn Chicago Central Loop — Sitting at 245 S. Franklin Street in the heart of the Loop financial district, this well-regarded hotel earns consistently strong marks for its comfortable rooms, helpful staff, and proximity to the Willis Tower and Chicago Riverwalk. It is a sensible, reliable choice with excellent value for money by downtown Chicago standards. Rated 9.0/10 on Booking.com from 318 reviews. 👉 Book on Booking.com
🛏️ Budget — HI Chicago Hostel — Sitting on the southern edge of the Loop near Lake Michigan, this well-run Hostelling International property is an exceptional budget option in a city where central accommodation can be expensive. Guests praise the spacious common areas, secure locker facilities, and the genuinely prime location — a short walk from Millennium Park, Michigan Avenue, and the Museum Campus. Rated 8.6/10 on Booking.com from nearly 10,000 reviews. 👉 Book on Booking.com

🟠 2. River North

River North is widely regarded as the most vibrant and entertaining neighbourhood in downtown Chicago, a densely packed district immediately north of the Chicago River that positively buzzes with energy seven nights a week. It boasts the highest concentration of art galleries in the city, a remarkable collection of restaurants spanning virtually every cuisine imaginable, and a nightlife scene that draws visitors from across the Midwest and beyond. The famous Restaurant Row along Ontario and Ohio Streets is a destination in itself, and the neighbourhood’s proximity to both the Magnificent Mile and the Loop means that sightseeing is effortlessly accessible. The House of Blues, Second City comedy club, and the Chicago Riverwalk are all within easy walking distance, and two different ‘L’ train stops provide convenient access to Wrigley Field to the north and the Museum Campus to the south.

What makes River North particularly appealing as a base is the sheer density of things to do within a very small area. Whether you are browsing contemporary art galleries during the day, dining at a celebrated chef’s latest venture in the evening, or enjoying craft cocktails at a rooftop bar after dark, the neighbourhood sustains interest effortlessly. It is also one of the more walkable parts of the city; a leisurely stroll north leads up to the Magnificent Mile’s high-end shopping along Michigan Avenue, while heading south over the river places you in the heart of the Loop within minutes. River North tends to attract a younger, more design-conscious crowd, and the hotel offerings reflect this, with everything from ultra-luxurious towers to quirky budget motels on offer.

🏨 Where to Stay in River North

⭐⭐⭐⭐⭐ Upscale — The Peninsula Chicago — One of the most consistently celebrated hotels in the entire country, The Peninsula sits at 108 East Superior Street at the southern end of the Magnificent Mile, delivering an exceptional level of service and elegance that earns it a place in the very top tier of Chicago accommodation. The two-storey spa, rooftop bar, and celebrated Avenues restaurant are genuine highlights, and the rooms — with their deep soaking baths and extraordinary attention to detail — are among the finest in the city. Rated 9.6/10 on Booking.com from over 1,000 reviews. 👉 Book on Booking.com
⭐⭐⭐ Mid-Range — Fairfield Inn & Suites Chicago Downtown/River North — Offering a free buffet breakfast, well-appointed rooms, and an excellent location close to two ‘L’ stations and mere blocks from the Magnificent Mile, this Marriott-brand property offers outstanding value for a central Chicago address. Staff are consistently praised for their friendliness and helpfulness, and the no-frills but comfortable rooms provide everything a visitor needs after a long day of sightseeing. Rated 8.5/10 on Booking.com from over 1,400 verified reviews. 👉 Book on Booking.com
🛏️ Budget — Ohio House Motel — A delightfully retro mid-century motel that has been serving guests in the heart of River North since 1960, the Ohio House is a genuine Chicago original. Its vintage diamond-motif signage, clean and comfortable rooms, and unbeatable location within walking distance of the Magnificent Mile make it one of the city’s best-kept budget secrets. Guests repeatedly highlight the remarkably friendly staff and the superb value for money. Rated 8.3/10 on Booking.com from nearly 2,000 reviews. 👉 Book on Booking.com

🟡 3. Gold Coast & the Magnificent Mile

The Gold Coast is Chicago at its most glamorous and historic, an affluent lakeside neighbourhood immediately north of downtown that has been associated with wealth and elegance since the late 19th century. Its streets are lined with beautifully preserved historic mansions, brownstones, and grand apartment buildings, many dating back to the Gilded Age, which create a sense of architectural continuity and distinction quite unlike anywhere else in the city. Oak Street — often described as the Rodeo Drive of the Midwest — offers the city’s finest luxury shopping, while the Magnificent Mile stretching south along Michigan Avenue packs in roughly 450 shops, flagship stores, celebrated restaurants, and iconic landmarks such as the John Hancock Center (875 North Michigan Avenue) and the historic Water Tower, one of the few buildings to survive the Great Chicago Fire of 1871.

Staying in the Gold Coast or along the Magnificent Mile places you in the geographic centre of everything a tourist could want. To the east, Oak Street Beach and the North Avenue Beach provide some of the city’s best swimming and people-watching in summer. To the south, a short walk brings you to the River North restaurant district and the Loop beyond. Cultural highlights are immediate: the Museum of Contemporary Art Chicago is a short stroll away, and Navy Pier — with its Ferris wheel, restaurants, and summer fireworks — extends spectacularly into Lake Michigan just minutes from your hotel. The area’s wide pavements and manicured streetscapes make it a genuinely pleasant neighbourhood to explore on foot, and the sense of being immersed in Chicago’s most storied and elegant quarter is not easily forgotten.

🏨 Where to Stay on the Magnificent Mile & Gold Coast

⭐⭐⭐⭐⭐ Upscale — Waldorf Astoria Chicago — Nestled in the heart of the Gold Coast at 11 East Walton Street, the Waldorf Astoria is a breathtaking French-inspired property housed in a stunning Art Deco building, offering what many consider the finest hotel experience in Chicago. The award-winning Guarneri spa, celebrated Brass Tack restaurant, fireplaces in many of the 214 lavishly appointed rooms, and a level of service that regularly draws superlative reviews make this the obvious choice for those seeking true luxury. Rated 9.4/10 on Booking.com from over 1,000 reviews. 👉 Book on Booking.com
⭐⭐⭐ Mid-Range — Voco Chicago Downtown – Riverwalk by IHG — This appealing 3-star hotel in River North, right on the edge of the Magnificent Mile, earns outstanding reviews for its welcoming staff, lively bar, and excellent location on the Chicago Riverwalk. It is a polished, contemporary hotel at a price point that makes it far better value than many of its neighbours, and the walkability to Magnificent Mile shopping and River North dining is exceptional. Rated 8.8/10 on Booking.com. 👉 Book on Booking.com
🛏️ Budget — Moxy Chicago Downtown — The Moxy brand is specifically designed for travellers who want a central location and fun atmosphere without paying premium prices, and this River North outpost delivers both in abundance. The vibrant, game-filled lobby bar, lively weekends with a DJ, and compact but cleverly designed rooms attract a sociable crowd. Its location just blocks from the Magnificent Mile and multiple ‘L’ stops makes it extremely good value for money at a prime downtown address. Rated well on Booking.com from hundreds of reviews. 👉 Book on Booking.com

🟢 4. Wicker Park & Bucktown

Wicker Park and its neighbour Bucktown are where Chicago sheds its corporate skin and reveals its creative, independent soul. Located roughly three miles north-west of the Loop and easily reached on the Blue Line ‘L’ train, this pair of adjacent neighbourhoods has evolved over the past three decades from a gritty artistic enclave into one of the most fashionable and sought-after addresses in the city. The streets around the six-corner intersection of North, Milwaukee, and Damen Avenues are packed with vintage clothing boutiques, independent record shops, craft cocktail bars, tattoo parlours, acclaimed restaurants, and art galleries that feel genuinely local rather than curated for tourists. Weekend brunch spots have long queues, evenings hum with live music and comedy, and the general atmosphere is one of creative energy and neighbourhood pride.

Choosing to stay in Wicker Park or Bucktown is a statement of intent: you want to experience Chicago as a Chicagoan rather than as a conventional tourist. That said, it is far from inconvenient. The Blue Line offers a quick and direct journey into the Loop, and the neighbourhood itself rewards extended exploration on foot. The famous Wicker Park Farmers Market, the wonderfully bohemian Double Door live music venue, and an extraordinary density of excellent independent restaurants make this one of the most enjoyable neighbourhoods in the entire United States for a food-and-culture-focused visit. Accommodation options are more limited here than downtown, but what exists tends to be characterful, affordable, and genuinely embedded in the local community.

🏨 Where to Stay in Wicker Park & Bucktown

⭐⭐⭐⭐ Upscale — The Robey, Chicago — Housed in a beautifully restored 1928 Art Deco tower at the heart of the six-corner intersection, The Robey is the neighbourhood’s defining hotel — a place of hardwood floors, 400-thread-count sheets, Bluetooth sound systems, and sweeping city views from its rooftop bar, The Up Room. Multiple on-site dining outlets, including Café Robey and the seasonally operated Solana rooftop, make it a destination in its own right. It is not a 5-star hotel in the traditional sense, but it comfortably delivers a boutique luxury experience that perfectly matches the neighbourhood’s creative spirit. Rated 8.8/10 on Booking.com from over 267 reviews. 👉 Book on Booking.com
⭐⭐⭐ Mid-Range — Hyatt Place Chicago/Wicker Park — A reliable, comfortable, and well-located option for those who want the Wicker Park experience with the reassurance of a trusted brand behind them. Offering spacious rooms, free Wi-Fi, and a location that puts the neighbourhood’s best restaurants and bars within easy walking distance, it serves as an excellent base for exploring both Wicker Park and the wider city. Rated well on Booking.com. 👉 Book on Booking.com
🛏️ Budget — Wicker Park Inn — A charming boutique bed and breakfast set in a lovingly restored 1886 historic home, the Wicker Park Inn is a genuinely special budget option — though ‘budget’ here means exceptional value rather than compromise. The nine individually decorated en-suite rooms, complimentary continental breakfast, and the warmth of the owner-operated atmosphere make it feel more like staying with a knowledgeable local friend than checking into a hotel. The location in the beating heart of Wicker Park is faultless. Rated 9.0/10 on Booking.com. 👉 Book on Booking.com