The secrets of Chicago, Illinois aren’t handed to you all at once. The city prefers to be discovered block by block, district by district. Among its 77 distinct communities, representing a diverse array of cultures, people, and experiences – a few stand out for visitors seeking charm, character and the best of the city’s cuisine. Here’s how to uncover the soul of Chicago, one neighbourhood at a time.
Near North Side
A stay at Hotel EMC2 sets the tone for something special. The Marriott Bonvoy boutique property feels like a love letter to Einstein and Da Vinci – high ceilings filled with books, beakers and bold modern art. Leo and Cleo, the hotel’s in-house robots, glide silently down hallways delivering room service, while the three lifts shift hues in RGB tones, expressing the easy merging of science and art. At the hotel’s restaurant, Albert (get it?), try delicate fried artichoke with lemon gremolata as well as the flawless orecchiette with broccolini and Italian sausage – comforting and clever.
Just steps away, you’ll find the Museum of Contemporary Art, a bold, often surprising collection that never plays it safe. And for afterwards, the nearby Beatrix café serves a breezy Baja chopped salad and pastries worth the queue.
Navy Pier remains an icon, and the 360 Chicago observation deck at the Hancock Tower provides the kind of skyline view that you came to this city for. Then there’s the Magnificent Mile, Chicago’s answer to the Champs-Élysées, made even better by its Netherlands partnered tulip-lined pavements and designer bags swinging from each wrist.
If shopping’s not your thing – then cycle around the city with Bobby’s Bike Hike. They offer curated tours, including a foodie tour that takes you through some of the central districts, testing Chicago’s eclectic taste in cuisine. At night, Three Dots and a Dash offers cocktails in everything from skull mugs to snowmen, served beneath glowing tiki torches. Try a group cocktail for theatrical flair, and maybe a headache tomorrow.
The Loop
In the heart of Chicago’s business district lies The Dearborn, a brasserie that’s anything but buttoned-up. Run by Irish-born sisters Amy and Clodagh Lawless, it nails both flair and flavour – especially the buffalo buttermilk chicken burger, dripping in house-made sauce with a rich blue Boursin kick.
Of course, you can’t come to the Loop without waving at The Bean (technically “Cloud Gate”) in Millennium Park. More thrilling though, is the Skydeck at Willis (formerly Sears) Tower – a glass box extending out over the city. And just nearby, the First Lady Architecture River Cruise departs on its legendary trip along the water, revealing landmark after landmark with witty commentary from volunteers of the Chicago Architecture Centre.
No Loop visit is complete without a slice from Lou Malnati’s, whose deep dish pizza is less a meal and more a rite of passage.
West Town
In Fulton Market, the mood is young, bold and unapologetically delicious. Chef Stephanie Izard’s Duck Duck Goat is a Chinese-American mashup that thrills – hand-pulled Xi’an Goat Slap Noodles, house-made dumplings and duck fried rice will have you booking your next visit on the spot.
Around the corner, the West Side Foodie Tour takes you from Roman square slices at Bonci Pizza, to Kasia’s buttery perogies, and onto bold, smoky flavours at Antique Taco.
Lincoln Park
The cycle tour takes you into the neighbouring district of Lincoln Park – not the band. A graceful mix of lakefront paths and old-town charm, Lincoln Park is Chicago’s refined exhale. It’s a neighbourhood of calm corners, ideal for lingering over coffee or wandering into boutiques.
At Maison Parisienne, the lemon tart is their iconic order, best enjoyed before a slow walk along the neighbourhood’s lakeside beaches, where the skyline peeks through trees and serenity feels entirely deliberate.
Uptown
In this quieter district sits Malt Row, a must-visit gem for beer and spirit aficionados. Work your way down Ravenswood at stops like Begyle Brewery – with fun sours like “When Tangerines Fly” and imperial stouts with the richness of coffee. Dovetail Brewery, on the other hand, is precise and steeped in European tradition, with lagers and hefeweizens served in a cavernous, barrel-filled loft.
Next door, Koval Distillery – the first to open in Chicago after Prohibition – is making waves with organic whiskey, gins and liqueurs. Book a tasting, go for a drink, but either way – try the remarkable cranberry gin liqueur.
Lake View
Even if you’re not catching a Cubs game at the iconic Wrigley Field, this area has a neighbourhood feel that draws families and travellers alike. Crosby’s Kitchen is a relaxed spot with standout dishes like lobster devilled eggs and a brussels sprout salad that somehow makes bacon and blueberries work together.
It’s also a great spot to try out a Chicago Greeter tour – a free, volunteer-led programme that matches visitors with passionate locals. Greeters operate in every corner of the city, offering insight into neighbourhoods you might not find in a guidebook. Think of it as borrowing a friend with insider knowledge – no awkward group selfies required, but I still took plenty.
Logan Square
Logan Square wears its cool effortlessly. With tree-lined boulevards, grand greystones and an independent spirit, it’s the sort of place where creatives, chefs and musicians actually live – not just perform. The neighbourhood buzzes with cocktail dens, offbeat galleries and a music scene that doesn’t wait for the weekend.
By day, Andros Taverna keeps things bright and Mediterranean – fresh oysters, the best grilled octopus in Chicago, ouzo-soaked pineapple and an incredible beetroot and feta salad. By night, Rosa’s Lounge fills with the kind of blues that put Chicago on the map. It’s not polished – it’s personal.
Grand Boulevard
Rich in cultural history and known as part of the historic Bronzeville area, Grand Boulevard once echoed with the footsteps of legends – musicians, activists, poets. Today, it’s reclaiming its spotlight with bold creativity, Black-owned enterprises and spaces that celebrate heritage.
Bronzeville Winery epitomises that new energy. A female- and Black-owned business, it offers wine flights themed by underrepresented winemakers – think Black-owned vineyards, women-led labels. The hand-battered Cajun shrimp is all crunch and fire, while the coconut curry salmon soothes everything it touches. There’s a live DJ, of course, and a crowd that knows the difference between scene and substance.
Chicago as a city is a mosaic of moods, cultures and experiences. Whether you’re being served by a robot, sipping cocktails from a skull, or drinking your way through a brewery corridor, there’s a district doing things its own way. With the CityPass booking app at your fingertips, and the Chicago Greeter tour guides answering any question you have, you can navigate it all with ease. Just don’t be surprised if you leave wanting more.
- Hotel ECM2
- Museum of Contemporary Art
- Beatrix restaurants
- Navy Pier
- 360 Chicago
- Magnificent Mile
- Bobby’s Bike Hike Westside Foodie Ride Bike Tour
- Three Dots and a Dash
- The Dearborn
- The Skydeck
- First Lady Cruises
- Lou Malnati’s
- Duck Duck Goat
- Bonci Pizza
- Kasia’s Deli
- Antique Taco
- Maison Parisienne
- Ravenswood’s Malt Row
- Begyle Brewery
- Dovetail Brewery
- Koval Distillery
- Wrigley Field
- Crosby’s Kitchen
- Chicago Greeter Tours
- Andros Taverna
- Rosa’s Lounge
- Bronzeville Winery
- CityPass
