From architecture and fine art, to endless live music events and a thriving theatre scene, there is always something surprising in the Windy City

Exploring the Windy City’s diverse neighbourhoods, from the Gold Coast to Magnificent Mile, is key to discovering what makes Chicago tick. (Please, don’t call it Chi-town.) Below our Chicago City Guide helps you prepare for the perfect blend of sophisticated culture and Midwestern hospitality.

Panoramic views and posh rooms are the stuff of Chicago hotels

Rooms with a view or two

Lobby. The Langham Chicago

The Lobby. Photo by the Langham Hotel, Chicago

Bedding down for the night in a Mies van der Rohe building is part of The Langham allure. Rooms offer panoramic views of Lake Michigan and the Chicago River and there’s that 20-metre swimming pool. From US$383.

Book-lover’s dream

Staying in the Author Suite on the 46th floor of the Four Seasons Chicago means you have the hotel’s extensive literary collection all to yourself. The award-winning Allium Restaurant & Bar promises fine lobster nachos and a Chicago Dog “with house-made everything.” From US$358.

Portable VIP

PHOTO: Chicago Peninsula

Through the Keys to the City program, guests at the Peninsula Chicago get special access to VIP lounges in the city, personal tours of the Michelin-starred Grace Restaurant and are fast-tracked through museums and gallery lineups. From US$535.

Everything old is new again

Thanks to a $100-million renovation, the 434-room Ritz-Carlton Chicago has swapped its traditional design for a more modern vibe. Great views of the pier from the Rooftop at Torali bar or from a treadmill in the fitness centre. From US$329.

Make it a spa day

Lobby. PHOTO: Waldorf Astoria

Lobby. PHOTO: Waldorf Astoria

After a day spent touring the Windy City, spoil yourself with the Waldorf Cleanse in the spa at the Waldorf Astoria Chicago. Well-appointed rooms on the northwest corner of the hotel overlook the iconic Gold Coast neighbourhood. From US$375.

Deep dish pizza is a must, but so are the award-winning eateries

Michelin-starred dining

Panzanella | Heirloom Tomato, Cucumber, Burrata

Panzanella | Heirloom Tomato, Cucumber, Burrata. PHOTO: Next Restaurant

Chicagoans who’ve patronized Grant Achatz’s three-Michelin-starred Alinea now line up for the chef’s themed tasting menu at his latest eatery, Next. Insider tip: The prix-fixe menu costs less on weeknights.

From a sow’s ear

James Beard award-winner Jimmy Bannos, owner of The Purple Pig, has a thing for pork. Try the pork saltimbocca with prosciutto and honey or the sweet and crunchy pig’s ears.

No-frills thrills

PHOTO: Schwa Restaurant / ?: @jayp_orig.215

BYOB. Minimalist setting. No coat check. The cooks at Michael Carlson’s 26-seat, 1 Michelin Star – Schwa Restaurant serve your food. The menu changes every six weeks, but almost always includes the popular parsnip custard with candied sweetbreads. Book ahead.

The art of donut-making

How about an Horchata Old Fashioned Boston Cream? The Doughnut Vault specializes in artisanal donuts at its two locations (North Franklin and North Canal).

Oh, for the love of goat!


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A post shared by Cabra Chicago (@cabrachicago)

Top Chef winner Stephanie Izard, who’s behind a handful of successful Chicago restaurants, serves up sophisticated takes on traditional  Peruvian Cuisine at Cabra Chicago. Pollo a la Brasa: half cornish hen, yuca fries, ají verde, aj́i pickes, salsa criolla is a must! Her other restaurants are Little Goat Diner, Girl & The Goat, Duck Duck Goat.

Chicago mixologists think outside the glass

Creative cocktails in Fulton Market

The Kimchi

If you’re thirsty and peckish in Fulton Market, The Aviary serves a five- or seven-course cocktail-and-food tasting menu that should satisfy both needs. Try the Kimchi, a blend of kimchi juice, soju, granny smith, and cucumber.

A chocolate chip cookie with that cocktail?

Gin-infused cocktails rule at the Victorian-style Scofflaw Bar in Logan Square. Complimentary chocolate chip cookies are served at midnight.

Behind the façade

Lie Chi & Steal: Wild Turkey 101 Bourbon, Cihuatan Jade Rum, lychee, ginger, honey, coconut & lime bitter.

Lie Chi & Steal: Wild Turkey 101 Bourbon, Cihuatan Jade Rum, lychee, ginger, honey, coconut & lime bitter.

The James Beard award-winning Violet Hour Bar is dedicated to artisanal cocktails. Consider the Lie Chi & Steal: Wild Turkey 101 Bourbon, Cihuatan Jade Rum, lychee, ginger, honey, coconut & lime bitter. No cell phone use inside the lounge.

Impressionists, improv, innovative theatre and more

Art Insitute of Chicago


Plan your art attack!

The Art Institute of Chicago is mammoth. If strapped for time, head directly to the Impressionist galleries. Expect fewer lineups at lunchtime and early afternoon.

The right cruise

Riverboat cruises are plentiful. However, Chicago Architecture Foundation’s tours are led by specially trained docents who are well-versed in the architectural wonders along the Chicago River.

Heights of fancy

Panoramic Views of Chicago from the skydeck

Panoramic Views of Chicago from the the Ledge. Photo by @tibosantacruz

Catching the view from the Skydeck atop the 412-metre Willis Tower is a rite of passage for first-time visitors to Chicago. Insider tip: arrive just before dusk to glimpse the cityscape at night.

Get your game on

Wrigley Field encapsulates more than 100 years of baseball history. Remember that tours held on game-days do not include a Club House visit.

They’re funny that way

Tina Fey and Steve Carell crafted their improv at the Second City Comedy Club in Chicago. For great sketch comedy, book tickets for Mondays at 8pm or weekends at 4pm.

Now for something completely different

The Neo-Futurists have been performing fast-clipped experimental theatre since 1988. In their Too Much Light Makes the Baby Go Blind, the troupe performs 30 plays in 60 minutes. Oh, and your ticket price is determined by a throw of the dice.

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