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*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

Book Air Canada flights to Chicago (ORD)

Chicago city guide

Lost Lake

For the banana daiquiris

Renowned bartender Paul McGee and co-owner Shelby Allison have created the ideal tiki-style escape, any time of the year. Drinks like the frothy banana daiquiri come bedecked with flowers and other Instagrammable accoutrements. Snacks from executive chef Fred Noinaj (try the coconut-shrimp toast or caramel-fish-sauce wings) set you up perfectly for another round.


For the Korean shared plates

Chef-owner Jennifer Kim, an up-and-comer on the Chicago dining scene, presents a wholly personal take on Korean fare, which she melds with Italian influences. Case in point: the housemade rice cakes dressed with lamb ragu. Order an array of sharables to start, then finish with the short-rib kalbi, sided with kimchi and other seasonal banchan.


For the splurge-worthy tasting menus

With three tasting menus – choose from 7, 12 or 20 courses – dinner at the two-Michelin-starred Smyth is pricey, but worth the splurge. Husband-and-wife team John and Karen Shields have many ingredients grown specifically for them on a nearby farm, and the resulting dishes, which change daily, are an inventive take on Midwestern fare. Reservations are a must.

U.B. Dogs

For hot dogs with all the toppings

Hot dogs are a Chicago delicacy, and this lunch-only spot serves some of the best in town. Order the classic Chicago, all-beef on an S. Rosen poppy-seed bun, or the house specialty: the Joey dog, dressed with fries and garlic-wasabi aioli. If you don’t fancy a frank, other options include a halal burger and Italian beef sandwich.

Pizzeria Bebu

For the thin-crust pies

The city may be known for deep-dish pizza, but many Chicagoans are partial to thin-crust pies, making Pizzeria Bebu a true local favourite. The pizzas come decked out with imaginative toppings, like carbonara or spicy vodka sauce. Can’t decide? Order the half-and-half and try two different flavours.

Baker Miller

For the all-day brunch

House-ground flours and grits form the basis for the baked goods and brunch dishes at this cozy café. The oatmeal, topped with cream and jam, is rightly called “famous,” while the ever-changing array of pastries includes scones, cakes and pies. For a tasty souvenir, buy take-and-bake sourdough cinnamon rolls to make when you go home.

Dark Matter Coffee

For the freshly roasted beans

One of Chicago’s best local coffee roasters, Dark Matter has multiple locations (including a new one, Caravanserai, with Mexican drinking chocolate), but the first location, dubbed the Mothership, is a good place to start. Try barrel-aged coffee, or cool down with an iced Chocolate City coffee, served on draft.

The iO Theater

For the laughs

This comedy club, which also offers improv classes, is the best spot to see up-and-coming acts: alums include Tina Fey, Amy Poehler and Stephen Colbert. Most shows begin with an audience suggestion, then spiral from there. Grab a drink or snack at the central bar post-show and mingle with the performers.

Art Institute of Chicago

For the artistic masterpieces

With thousands of works of art on display, including Edward Hopper’s Nighthawks and Grant Wood’s American Gothic, two wings and special exhibits, it’s easy to lose yourself here for the day. If you don’t have that long, snag a brochure at the entrance that details how to fit the museum’s highlights within an hour.

Garfield Park Conservatory

For the urban jungle

When Chicagoans need a dose of lushness in the depths of winter, they head to this conservatory – free and open 365 days a year – for lofty spaces filled with palms and ferns (the latter evoking the prehistoric local landscape). Come summer, explore 12 acres of outdoor gardens, including a Play & Grow area designed for kids.

Chicago Architecture Center: Art Deco Skyscrapers Tour

For the art deco landmarks

A river cruise will show you the sights, but understanding the city’s rich architectural history demands closer attention. This 90-minute walking tour through the Loop includes visits to the lobbies of four art deco landmarks, including the quintessential Chicago Board of Trade building, for a more detail-oriented experience.

The Green Mill

For the jazz acts

This more-than-century-old jazz club is legendary – Al Capone was a regular – but somehow manages to be non-touristy. Expect a fresh lineup of jazz acts nightly, plus weekly events like open poetry slams. You can catch music until the wee hours most nights (with some shows running until 5 a.m.), so it’s a perfect stop for a lively nightcap.

Wicker Park

For the fashionable indie stores

Milwaukee Avenue in Wicker Park is packed with local independent shops, including Una Mae’s (a destination for new and vintage clothing and home decor), Reckless Records and Volumes Bookstore. Pick up flowers and jewellery at Asrai Garden, or men’s denim at Mildblend Supply Co. Between stops, refuel at Chicago favourite Intelligentsia Coffee.

Humboldt House

For the locally made homeware

Claire Tibbs has stocked her sunny shop with finds by Chicago makers, perfect as gifts for others or yourself. Find brass cuffs by Lindsay Lewis, speckled mugs by Commune Pottery, and hand-poured scented candles by Tatine Candles. Sister shop Little Peach Fuzz, a block south, features toys and books for kids.

Lost Girls Vintage

For the cheerful vintage womenswear

This funky, brightly coloured shop is a popular haunt for vintage-clothing lovers, whether you’re scouring the city for a Victorian blouse or 1970s glitter dress. Clothing sizes range from 00 to 26 – a partnership with Luvsick Plus, which specializes in vintage for curvy women, means you will find inclusive options on offer.

Unabridged Bookstore

For the recommended reads

It’s hard to leave this beloved store without a tote full of new books, thanks to personal recommendations from staff (on handwritten notes peppered around the shelves), a featured book of the week highlighting lesser-known writers, and a large selection of marked-down titles.

The Robey

For the rooftop scene

Revamping two historic buildings – an art deco skyscraper and an adjacent industrial warehouse – this hip hotel offers minimalist rooms flooded with natural light. Head to the rooftop for impressive 360-degree views, where you will also find a happening pool scene in summer. Come winter, wind down in the Up Room cocktail bar with an on-point old-fashioned.

Chicago Athletic Association

For the buzzy atmosphere

A boisterous private club for more than 115 years, the Chicago Athletic Association remains one of the city’s best spots to socialize in its latest incarnation as a boutique hotel. You can dine at seven bars and restaurants without stepping outside (though the location, facing Millennium Park, is prime for sightseeing). Settle by the fireplace in the Drawing Room, where locals and travellers converge over oysters, local brews and classic cocktails.

Ace Hotel Chicago

For the centre-of-everything location

It would be easy to spend all your time at the Ace, grabbing a cold brew at Stumptown or dining at City Mouse (a partnership with the critically adored restaurant Giant). But the West Loop is also home to more than 100 restaurants and bars – and counting – all walkable from the hotel. Borrow a Tokyobike from the front desk to explore farther afield.

Viceroy Chicago

For the elegant stay

If you’re here to splurge, it’s hard to top the Viceroy, where you will find plush rooms (the smallest is 337 square feet), rides in the hotel’s Tesla, and complimentary bike rentals to wheel around the Gold Coast area. Dining at Somerset is a must – Michelin-starred chef Lee Wolen serves one of the best fried-chicken sandwiches in town.

The Langham, Chicago

For the business amenities

If you’re in town on business, this Ludwig Mies van der Rohe-designed building on the Chicago River is walking distance to nearly everywhere you will need to go. Join the Langham Club (for an extra fee) for numerous handy amenities, including a 4,000-square-foot lounge with all-day refreshments, boardroom access and complimentary local car service.

Info about getting from the airport, public transportation and more.

Getting From the Airport

To get a taxi at O’Hare International Airport, head to the pickup areas, at the lower-level curbside outside baggage claim, at each of the four terminals. A cab downtown costs approximately US$30–$40, or US$24 per person for a shared ride; expect the trip to take about 30 - 45 minutes.

The Chicago Transit Authority (CTA) also operates a Blue Line train to and from O’Hare. A US$5 ticket will get you downtown (to Jackson station) in about 45 minutes.

Public Transportation

The CTA operates buses and "L" train throughout the city. A bus fare is US$2.25 and a train fare is US$2.50, with daily passes starting at US$10.


Taxis are available around the city, but harder to find outside downtown. To book in advance, the city offers two apps, Arro and Curb. Uber and Lyft also operate in Chicago.


The bikeshare service Divvy has numerous pickup and drop-off spots around the city. One 30-minute ride costs US$3, and day passes go for US$15. You can rent at the kiosks, or save time by downloading the app. Besides riding around town, the lakefront has a bike path with lake and skyline views.

Weather in Chicago

Monday light rain
4°C Oct 26, 2020
Tuesday broken clouds
6°C Oct 27, 2020
Wednesday sky is clear
10°C Oct 28, 2020
Thursday overcast clouds
9°C Oct 29, 2020
Friday broken clouds
7°C Oct 30, 2020
Saturday few clouds
10°C Oct 31, 2020
Sunday sky is clear
10°C Nov 01, 2020
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Book today for the lowest fares to Chicago

There are no flight results that match your filtered criteria. Please adjust your search criteria.

*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.