Flights to Chicago from CAD198*
Lowest Fares to Chicago
CAD
From Toronto (YTO) to Chicago (MDW)
Apr 12, 2025
Starting from
CAD202*
Seen:1dayago
One-way fare/Economy
From Toronto (YTZ) to Chicago (MDW)
Apr 15, 2025
Starting from
CAD202*
Seen:5hoursago
One-way fare/Economy
From Ottawa (YOW) to Chicago (MDW)
Apr 15, 2025
Starting from
CAD277*
Seen:5hoursago
One-way fare/Economy
From Montreal (YUL) to Chicago (MDW)
Apr 16, 2025
Starting from
CAD220*
Seen:4hoursago
One-way fare/Economy
From Thunder Bay (YQT) to Chicago (MDW)
Apr 06, 2025
Starting from
CAD254*
Seen:5daysago
One-way fare/Economy
From Halifax (YHZ) to Chicago (MDW)
Apr 14, 2025
Starting from
CAD241*
Seen:2daysago
One-way fare/Economy
From Moncton (YQM) to Chicago (MDW)
Mar 25, 2025
Starting from
CAD398*
Seen:2daysago
One-way fare/Economy
From Sault Ste. Marie (YAM) to Chicago (MDW)
Apr 16, 2025
Starting from
CAD229*
Seen:4daysago
One-way fare/Economy
From Fredericton (YFC) to Chicago (MDW)
Apr 01, 2025
Starting from
CAD470*
Seen:16hoursago
One-way fare/Economy
*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.
Miles and miles of magnificence
From architecture and fine art, to endless live music events and a thriving theatre scene, the Windy City will blow you away when you book flights to Chicago.
Make Millennium Park your first stop when your flight to Chicago lands. This popular park hosts free concerts on summer evenings and is full of famous attractions and art displays, including Anish Kapoor’s iconic Cloud Gate, more widely known as “the Bean”. There’s fun to be had in winter at the McCormick Tribune Ice Rink and in summer when it converts to outdoor dining as the Park Grill Plaza.
After your flight to Chicago lands, take in the beautiful artwork that’s found at the Art Institute of Chicago. This museum, founded in the late 1800s, is the second largest in the country and boasts incredible collections of international art, contemporary photography, and architecture. With thousands of pieces and stunning architecture, this top tourist attraction is sure to keep even the most casual art lover busy for hours.
Experience more of Chicago’s architectural wonders through its endless venues that house its expansive music scene. Annual lakefront jazz and blues festivals beautifully capture Chicago’s musical history, but there are always tons of choices for fans of every genre.
Flights to Chicago continue to entertain when you visit the Navy Pier. Start off your time at the pier by enjoying a cold one alongside lakefront views from the beer garden. After your drink, set sail on a boat cruise or skate by the lake at Chicago’s outdoor summer ice rink. In between adventures, you’ll spot public art, sculptures, galleries, and gardens.
For some family fun at the pier, step right up with the little ones, who will love the carnival rides and three floors of interactive exhibits at the Chicago Children’s Museum. Kids will have a blast digging for dinosaur fossils, painting, and splashing around at an indoor waterpark.
Visit Shedd Aquarium and you’ll find yourself marvelling at the architecture as well as the colourful marine life. Opened in 1930, Shedd Aquarium is the largest indoor aquarium in the world. Dive in deep with thousands of freshwater and saltwater species from around the globe.
Discover endless entertainment and miles of magnificence when you book flights to Chicago.
Logan Square
Chicago’s hottest hood
Visit Logan Square to discover restaurants, shops, and attractions at every corner when your flight to Chicago lands.
Whether you’re shopping for your wardrobe or looking to add to your record collection, Logan Square is sure to have something in store for you. From the shelves of book and record shops to the racks of streetwear stores, explore this neighbourhood and you’re likely to find some unique boutique goods.
Take some time to relax after your flight to Chicago by visiting the beautiful Humboldt Park. The park offers stunning rose beds, tennis courts, an inland beach, baseball fields, bike paths, and a lagoon that’s perfect for swimming and fishing.
Surrounding the lagoon, you’ll find food trucks, gorgeous gardens, and frequent festivals to help you enjoy your stay. The Barrio Arts Festival attracts visitors each year with culture-focused lectures, food vendors, public workshops, and live performances.
At the heart of Logan Square is the neighbourhood's pulse where Milwaukee Avenue, Kedzie Avenue, and Logan Boulevard intersect. Milwaukee Avenue is dotted with dive bars with local charm and vintage arcade games, gourmet coffeehouses and cocktail lounges. Around this area you’ll also discover intimate music venues and beautiful tree-lined boulevards.
All sides of Logan Square are waiting to be explored when you book flights to Chicago.
Wicker Park
Big culture in a small package
Come and see what makes Wicker Park a local favourite when you book flights to Chicago.
Wicker Park is named after the public urban park at its centre. It became a part of Chicago in 1837 and has grown and diversified greatly over the years. Known for its local hipster culture, art community, nightlife, and food scene, Wicker Park is the perfect place to go for a hangout.
The park itself is the place to be to relax after your flight to Chicago. Here you’ll find indoor and outdoor movie screenings and an ice rink. You may even catch locals pitching a game of 16-inch softball, a Chicago invention dating back to the late 19th century.
Back on Wicker Park’s main streets, art buffs will find a few gems with Wicker Park’s collection of prestigious and innovative art spaces. Corbett vs Dempsey, established over a decade ago, is an absolute must for art lovers flying to Chicago. This creative space is a proud display of American modernism, abstract, and contemporary art.
When you’re feeling hungry, chow down in Wicker Park. With over 100 restaurants in the area, you’re sure to find something you’re feeling. Japanese, Thai, Italian, Middle Eastern cuisine, and French fusion feasts serve up food to satisfy every craving.
When you’re all done enjoying the neighbourhood, you’re in a great spot to easily discover more of what Chicago has to offer. The Loop and some of the city’s most famous landmarks are just an easy train ride away from Wicker Park.
With diverse food, culture-focused fun, and a pathway to other amazing attractions, be sure to visit Wicker Park when you book flights to Chicago.
Getting to Chicago Midway International Airport (MDW)
Porter’s check-in desk is located in concourse A.
Chicago Midway International Airport (MDW) is about 9 km / 6 mi from downtown Chicago.
Transportation
Taxis from downtown cost about $20 USD per person. Car service is available.
Car rental services are available at Chicago Midway Airport (MDW). Take the shuttle to the rental car area from the pick-up location at door 3 of the lower level, near the baggage claim area.
Please allow sufficient time to drop off your car rental before your departing flight.
Uber and Lyft pickup is available at Chicago Midway Airport. To find your ride, exit at the baggage claims level, exit through door 4, and cross the street. Fares from MDW to downtown Chicago start at $23.
The Go Airport Express shuttle bus provides service to the airport from downtown. The fare is $27 USD.
Take the Chicago Transit Authority orange line train from the Midway stop. The fare is $2.50 USD.
Chicago Midway International Airport Parking
Driving to Chicago Midway International Airport? There are many parking options at Chicago Airport. There are two economy parking lots with a rate of $2 USD for 30 minutes, $5 USD for 30 minutes to an hour, and a maximum of $15 USD for 24 hours. Or, choose the terminal garage, which offers hourly or daily rates. The daily lot has a 24-hour rate of $30 USD and is a long-term lot. You may also reserve a parking space ahead of time for a fee of $10 USD per space, per day.
The information and figures above are for reference only, and may not be current. Please visit each airport's website for up-to-date details.
Great deals to Chicago
CAD
| From | To | Dates | Fare Type | Price |
|---|---|---|---|---|
Toronto (YTZ) | Chicago (MDW) | Jun 15, 2025 | One-way fare/Economy | |
Toronto (YTO) | Chicago (MDW) | May 24, 2025 | One-way fare/Economy | |
Ottawa (YOW) | Chicago (MDW) | Apr 19, 2025 | One-way fare/Economy | |
Montreal (YUL) | Chicago (MDW) | Apr 17, 2025 | One-way fare/Economy | |
Thunder Bay (YQT) | Chicago (MDW) | Jun 02, 2025 | One-way fare/Economy | |
Halifax (YHZ) | Chicago (MDW) | May 05, 2025 | One-way fare/Economy | |
Moncton (YQM) | Chicago (MDW) | Apr 29, 2025 | One-way fare/Economy | |
Sault Ste. Marie (YAM) | Chicago (MDW) | Apr 17, 2025 | One-way fare/Economy | |
Fredericton (YFC) | Chicago (MDW) | Apr 25, 2025 | One-way fare/Economy | |
Charlottetown (YYG) | Chicago (MDW) | Jun 05, 2025 | One-way fare/Economy |
*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.