Chicago is a city that refuses to be summed up in a neat little package. Sprawling along Lake Michigan’s shore like a metropolis from a future past, it’s a place where world-class architecture meets Midwestern charm, where culinary innovation sits comfortably alongside classic hot dog stands, and where blues music still wafts from basement bars into the evening air.
First-time visitors often make the mistake of treating Chicago like a smaller New York – it’s not. The Windy City (a nickname that, surprisingly, refers more to the city’s historically boastful politicians than its weather) moves to its own distinctly Midwestern rhythm.
While guidebooks might send you scrambling between tourist spots, the real Chicago reveals itself in the spaces in between – in neighbourhood diners, local music venues, and quiet lakefront spots where the skyline takes your breath away. Here’s your insider’s guide to experiencing the city like a proper Chicagoan would show their favourite cousin around – mixing essential landmarks with those secret spots that make this city truly special.
Start Your Day At The Bean (But Do It Right)
Cloud Gate, universally known as ‘The Bean’, is Chicago’s most photographed artwork – a massive, mirror-polished stainless steel sculpture that looks exactly like, well, a giant bean. It perfectly reflects the city’s skyline and has become the unofficial symbol of modern Chicago. Yes, it’s touristy, but here’s the secret: arrive at 7am with a coffee from Intelligentsia on Randolph (their oat milk latte is worth the queue). You’ll have the whole place to yourself for photos, and watching the sunrise reflect off the sculpture is genuinely magical. Plus, you’ll dodge the Instagram crowds who arrive by the busload after 9am.
Read: How to make your travel photos look more professional
Get Lost In The Art Institute, But Skip the Obvious
Housing over 300,000 artworks, the Art Institute of Chicago spans 5,000 years of human creativity. Everyone rushes to American Gothic (you know, that famous painting of the stern farmer with his pitchfork), but head straight to the Modern Wing’s top floor instead. The city views through the massive windows are spectacular, and the Gerhard Richter collection is mindblowing. Pro tip: Thursday evenings are free for Illinois residents, and the crowd is mostly art students and locals.
Do Deep Dish, But Make It Pequod’s
First, let’s talk about Chicago deep dish pizza. Unlike its thin-crust Italian cousin, this is a beast of a different order – imagine a two-inch-deep crusty bowl filled with rivers of molten cheese, chunky tomato sauce, and whatever toppings you fancy. It’s more like a pie than a pizza, and it’s a Chicago institution.
Whilst the popular tourist traps Giordano’s and Gino’s East are certainly good, they get a little busy and aren’t perhaps the finest you’ll find in the city. Instead, head to Pequod’s in Lincoln Park, which serves the city’s best version with its signature caramelised cheese crust that’s worth the inevitable queue. Go at 4pm to avoid the worst of the wait, and order the pan pizza with sausage and giardiniera (Chicago’s beloved spicy pickled vegetable mix – it cuts through the richness perfectly).
Take That Architecture Cruise (But Choose Wisely)
Chicago is essentially an open-air museum of 20th-century architecture, where legendary architects like Frank Lloyd Wright, Mies van der Rohe, and Louis Sullivan left their mark. The Chicago Architecture Center’s cruises are worth every penny—specifically their 5:30pm summer tour when the light hits the buildings perfectly.
The 90-minute journey takes you down all three branches of the Chicago River, passing over 50 significant buildings, from art deco masterpieces to ultra-modern skyscrapers. Avoid the cheaper knockoffs; CAC’s volunteer docents are actual architects and architecture historians who know their stuff. Grab a seat on the port (left) side of the boat for the best photo ops.
Hit Big Star In Wicker Park for Taco Tuesday
In a city famous for its Mexican population (over 1.5 million in the metro area), choosing where to get tacos can be overwhelming. This converted petrol station serves the city’s best tacos al pastor (marinated pork sliced from a vertical spit and served with pineapple), and their whiskey list is extraordinary.
Sit on the patio, order the queso fundido with rajas (melted cheese with roasted poblano peppers), and watch the neighbourhood’s endless parade of characters go by. The queue can be mad, but the bar next door, Violet Hour (behind the unmarked door), makes the perfect waiting spot – it’s one of the spots that kicked off America’s craft cocktail revival in the early 2000s.
Read: The best Mexican food in London
Experience Teatro ZinZanni’s Spectacular Circus Dinner Show
Teatro ZinZanni offers something distinctly local – a blend of cirque-style acrobatics, classic Chicago speakeasy vibes, and a four-course feast. Housed in the historic Cambria Hotel in the Loop, this intimate venue puts you right in the middle of the action. The performers interact with diners throughout the evening, and the vintage spiegeltent setting makes you feel like you’ve stepped back into Chicago’s roaring twenties. Book the early show – the later one can run past midnight, and you’ll want to savour every moment.
Similarly theatrical, and among the most unique fun things to do in Chicago, Cirque du Soleil’s performances transform the city’s historic venues into otherworldly spaces. Whether they’re taking over the United Center (where the Bulls play basketball during regular season) or gracing the ornate Chicago Theatre with their presence, Cirque brings something special to the Windy City. The shows feel different here – maybe it’s the way the acrobatics echo off the Theatre’s 1920s French Baroque architecture, or how the lake wind sweeps around the United Center’s plaza before you step into their magical world. Unlike touring stops in other cities, Chicago performances often enjoy extended runs, allowing for more elaborate staging and rigging setups.
Book tickets well in advance – locals snap up the best seats months ahead, especially for winter shows when everyone’s looking for indoor entertainment. Pro tip: the seats in the first few rows of the mezzanine often offer better views of the aerial acts than the ground-level premium seats.
Catch Jazz At The Green Mill
The Green Mill isn’t just another jazz club – it’s a living piece of Chicago history. Built in 1907, this art deco time capsule was Al Capone’s favourite hangout during Prohibition, and if you know where to look, you can still spot the escape tunnels the mobsters used during raids. The spittoon-lined bar and vintage booths remain unchanged since the days when Charlie Chaplin performed here.
Sunday night’s Poetry Slam (the oldest in the country) is a Chicago institution, but the real magic happens during Tuesday’s jazz sessions when local legends drop in for impromptu performances. Get there early to snag one of the original wooden booths – they’ve been there since opening night.
Browse Myopic Books, Then Hit Stan’s Donuts
Independent bookshops are increasingly rare, but Myopic Books keeps the flame burning bright. This three-floor literary labyrinth in Wicker Park stays open until midnight and houses over 70,000 books, arranged in a charmingly chaotic system that encourages serendipitous discoveries. Their poetry section is unmatched, and the creaky wooden floors and resident shop cat (named Pages) make it properly atmospheric.
Afterwards, walk five minutes to Stan’s for their pocket doughnuts filled with Nutella. They’re best eaten on the Blue Line platform while watching trains rumble past – a quintessential Chicago moment.
Experience Logan Square’s Food Revolution
Ten years ago, Logan Square was just another working-class neighbourhood. Now it’s the epicentre of Chicago’s culinary renaissance. Skip River North’s overpriced restaurants and head northwest.
Start at Mini Mott for their legendary burger (originally a secret menu item at their sister restaurant that became so popular it needed its own venue), then bar-hop down Milwaukee Avenue.
End at Lula Cafe, a neighbourhood institution that pioneered farm-to-table dining in Chicago long before it was trendy. Their Monday night farm dinners are the stuff of local legend – each week’s menu is entirely different and based on what arrived that morning from local farms.
Get Local At Montrose Point Bird Sanctuary
Navy Pier might top the tourist lists, but locals know the real magic happens here. This hidden spot, nicknamed ‘The Magic Hedge’ by locals, offers the best skyline views in the city. Originally a Cold War Nike missile site, this 15-acre peninsula has been transformed into a crucial stopover for migratory birds. It’s where serious photographers catch sunrise over the lake, and during spring migration, you might spot rare warblers among the trees. Bring a thermos and watch the morning rowing crews glide past.
End Your Night In Pilsen’s Art District
Pilsen, Chicago’s heart of Mexican-American culture since the 1950s, is living proof that street art can rival anything hanging in galleries. This vibrant neighbourhood is home to some of the city’s most stunning murals – massive, building-sized works that tell stories of immigration, resistance, and celebration.
Start at 16th and Blue Island to see the best street art, then head to Thalia Hall, an 1892 opera house modelled after Prague’s State Opera House. End your night with mezcal cocktails at Caminos de Michoacan, where the jukebox plays nothing but vintage Mexican vinyl and the bartenders can tell you the story behind every bottle.
Local Know-How
- The Ventra app for public transport is essential, but keep a physical backup card—phone batteries die at the worst moments
- Chicago winters are brutal. That ‘Windy City’ nickname might refer to politicians, but -20°C with windchill is no joke
- Join the Chicago Architecture Center as a member if you’re staying more than a few days—the walking tours alone make it worth it
- The 606 elevated trail (Chicago’s answer to New York’s High Line) is lovely, but go early (before 9am) on weekdays to avoid the lycra-clad crowd
- Always carry cash—many of the best local spots still don’t take cards, particularly the old-school jazz clubs
- ‘The Loop’ refers to the elevated train loop downtown, not the whole city centre as some guides claim
- Don’t ask for ketchup on your hot dog at classic stands like Hot “G” Dog – it’s considered sacrilege in Chicago
Remember: Chicago’s not just about ticking off tourist spots—it’s about finding your own corner of the city to fall in love with. These recommendations aren’t exhaustive, but they’ll help you start exploring like a local rather than following the herd. And unlike many American cities, Chicago’s neighbourhoods are well connected by the ‘L’ train system, so you can easily explore beyond downtown without needing a car.