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About Flights to Chicago

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

C$ 97

Best Round-Trip Price

C$ 270

Fastest flight time

1h 47m

Operated By

3 airlines
The best one-way flight price to Chicago from Canada in the last 72 hours is C$ 97 (Toronto Pearson Intl to Chicago O'Hare Intl).
The best round-trip flight price to Chicago from Canada in the last 72 hours is C$ 270 (Toronto Island to Chicago Midway).
The fastest flight to Chicago from Canada takes 1h 47m (Toronto Island to Chicago Midway).
There are 3 airlines operating flights to Chicago, including British Airways, Air Canada and Porter Airlines.

Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

What is the cheapest month to fly to Chicago?

The month of November is another great option to travel to Chicago, with average flight prices from Canada averaging around C$ 315.

What is the absolute cheapest flight to Chicago?

Users booking trips to Chicago from Houston found flights 81% cheaper than the average price of flights to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.
See prices from:

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as C$ 318. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 362. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Canada to Chicago when you can find flight prices for as low as C$ 326. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the evening is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 389 per ticket.

How long does it take to fly to Chicago?

Flight times from Canada to Chicago vary, but if you’re flying out of Toronto Pearson Intl and flying into Chicago O'Hare Intl (one of the most popular routes), then the duration is 1h 32m on average. Another popular route from Canada to Chicago is flying from Vancouver Intl to Chicago O'Hare Intl, which will take roughly 3h 40m. Keep in mind that layovers or delays could extend your travel time.

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Canada is 60 days out, which is when prices tend to be around C$ 345.

Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
Toronto Pearson Intl Airport
Chicago O'Hare Intl Airport

CHEAPEST ROUTE FROM Toronto TO Chicago

Toronto Island Airport (YTZ) to Chicago Midway Airport (MDW)

Typically, flights to Chicago from Toronto are cheaper when flying from Toronto Island to Chicago Midway, which has an average price of C$ 333


Frequently asked questions about flying to Chicago

Hikers looking for a more family-friendly day in the great outdoors would be best suited to plan their flight to Chicago for September and October, when they can visit Grant Park and enjoy all that the park has to offer.

The best time to plan to fly to Chicago to go sightseeing would be when the temperature is not unbearable and the chance of rain is only moderate. Considering those guidelines, May or June seem like the best times of year to plan your visit.

Those flying to Chicago could potentially find better pricing at Chicago O'Hare Intl Airport (26 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre) depending on the month and departure airport.

Chicago Midway Airport has an average price of C$ 481 per person and is typically the cheapest airport to fly into when visiting Chicago. This average price does vary based on departure city. Try momondo’s Airport-to-Airport Pricing Tool to find the cheapest flight.

Yes, if you fly to Chicago Midway in Chicago which is the closest available airport to Logan Square (15.4 km away).

The closest airport to Magnificent Mile is Chicago Midway, 15.7 km away.


Chicago flight deals found on momondo

Check out some of the best fares from airports in Canada to Chicago found recently by users on momondo

Which airlines fly to Chicago?

Here you can see a selection of the most popular and cheapest airlines for flights to Chicago

Which airlines fly to Chicago?

When flying to Chicago from Canada, momondo travellers will most often fly with one of these popular airlines: Air Canada, Porter Airlines, United Airlines or American Airlines. Depending on what airport in Canada you fly from, you may be able to find flights with any of these popular airlines.

Egypt Air Flights to Chicago

Egypt Air will jet to Chicago around 3 times in an average week. Where you fly from will dictate what kind of deals you can get for Egypt Air, but prices as low as C$ 303 have been found from Toronto Pearson Intl to Chicago. Egypt Air has scored 7.7/10 in momondo user reviews.

WestJet Flights to Chicago

C$ 127 is the best round-trip WestJet deal to Chicago found on momondo in the last few days. The deal departed from Edmonton. WestJet has 50 flights to Chicago most weeks, with prices varying by availability. 124 momondo users have reviewed WestJet, scoring the airline a 7.4/10 on average.


Airports near Chicago

Below you will find all the airports in Chicago along with their distance from the city centre

Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration
Toronto to Chicago Flights
Fastest flight time1h 32m
Cheapest priceC$ 253
Vancouver to Chicago Flights
Fastest flight time3h 40m
Cheapest priceC$ 397
Montreal to Chicago Flights
Fastest flight time3h 57m
Cheapest priceC$ 283
Calgary to Chicago Flights
Fastest flight time3h 18m
Cheapest priceC$ 406
Ottawa to Chicago Flights
Fastest flight time3h 40m
Cheapest priceC$ 377
Edmonton to Chicago Flights
Fastest flight time10h 45m
Cheapest priceC$ 397
Winnipeg to Chicago Flights
Fastest flight time6h 11m
Cheapest priceC$ 451
Buffalo to Chicago Flights
Fastest flight time1h 52m
Cheapest priceC$ 294
Halifax to Chicago Flights
Fastest flight time6h 30m
Cheapest priceC$ 349
Grande Prairie to Chicago Flights
Fastest flight time16h 06m
Cheapest priceC$ 1,083
Kelowna to Chicago Flights
Fastest flight time11h 25m
Cheapest priceC$ 1,043
Québec City to Chicago Flights
Fastest flight time5h 45m
Cheapest priceC$ 327
London, Ontario to Chicago Flights
Fastest flight time3h 57m
Cheapest priceC$ 451
Victoria to Chicago Flights
Fastest flight time7h 30m
Cheapest priceC$ 739
Nanaimo to Chicago Flights
Fastest flight time37h 45m
Cheapest priceC$ 894
New York to Chicago Flights
Fastest flight time2h 50m
Cheapest priceC$ 268
Sudbury, Ontario to Chicago Flights
Fastest flight time6h 59m
Cheapest priceC$ 799
Los Angeles to Chicago Flights
Fastest flight time4h 10m
Cheapest priceC$ 644
Regina to Chicago Flights
Fastest flight time7h 10m
Cheapest priceC$ 502
Fort McMurray to Chicago Flights
Fastest flight time9h 01m
Cheapest priceC$ 792

Start planning your trip to Chicago


Why use momondo?

It is quick and easy to find flights to Chicago on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Yes. All flights to Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

momondo provides multiple filters to help you find the best flight to Chicago. Filter by price, airline, airport, cabin, aircraft, payment method, number of stops and more.

Yes momondo offers price alerts on flights to Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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