Find cheap flights to Chicago

Round-trip
Economy
Washington (WAS)
Chicago (CHI)
Mon. 13/7
Mon. 20/7
Any month
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Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
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When is the best time to fly to Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Canada, with most prices found around 298 C$. If you don’t want to visit Chicago in February, then you should wait until March to fly from Canada, when ticket prices are also cheap, with an average price of 310 C$.

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

We recommend purchasing flights from Canada to Chicago 60 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago for 339 C$. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Canada for as low as 255 C$ on momondo.

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 Wednesday when prices can be found for as low as 344 C$. This is often the case because there is less demand to fly during this day of the week. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Chicago on Monday is 373 C$.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Canada to Chicago during this time can be as low as 328 C$. If you have a flexible travel schedule, then try to avoid flying in the evening when prices are 366 C$ on average. Flights to Chicago from Canada in the evening are generally more expensive because this time of day is more convenient for travellers’ schedules.

Is there a good place to hike near Chicago?

If you’re looking to do your hiking in warmer conditions, consider planning your flight to Chicago for September and October. Parks like Grant Park are popular hot spots in those months.

When is it best to fly to Chicago to go sightseeing?

Sights like Magnificent Mile, Grant Park, and Chicago Theater are most enjoyable in months with moderate weather conditions like May or June. Plan your flight to Chicago for those months.


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
Cheapest
Best
Quickest
Japan Airlines
25 Sep.
YYZ
Toronto Pearson Intl
1h 55m
ORD
Chicago O'Hare Intl
27 Sep.
ORD
Chicago O'Hare Intl
1h 38m
YYZ
Toronto Pearson Intl
Porter Airlines
20 Oct.
YTZ
Toronto Island
1h 47m
MDW
Chicago Midway
4 Nov.
MDW
Chicago Midway
1h 37m
YTZ
Toronto Island
Delta
3 Nov.
YVR
Vancouver Intl
8h 38m
1 stop
ORD
Chicago O'Hare Intl
2 Dec.
ORD
Chicago O'Hare Intl
8h 41m
1 stop
YVR
Vancouver Intl
Multiple Airlines
18 Sep.
YYZ
Toronto Pearson Intl
1h 55m
ORD
Chicago O'Hare Intl
20 Sep.
ORD
Chicago O'Hare Intl
1h 34m
YYZ
Toronto Pearson Intl
Qantas Airways
23 Jun.
YYZ
Toronto Pearson Intl
1h 55m
ORD
Chicago O'Hare Intl
30 Jun.
ORD
Chicago O'Hare Intl
1h 45m
YYZ
Toronto Pearson Intl
British Airways
18 Sep.
YYZ
Toronto Pearson Intl
1h 52m
ORD
Chicago O'Hare Intl
20 Sep.
ORD
Chicago O'Hare Intl
5h 19m
1 stop
YYZ
Toronto Pearson Intl

Find the cheapest one-way flights to Chicago

If you're looking for one-way flights to Chicago, view some of our deals below provided by Porter Airlines and Lufthansa
Cheapest
Best
Quickest
Porter Airlines
12 Aug.
YTZ
Toronto Island
1h 47m
MDW
Chicago Midway
Lufthansa
12 Aug.
YYZ
Toronto Pearson Intl
1h 59m
ORD
Chicago O'Hare Intl
Delta
7 Sep.
YVR
Vancouver Intl
6h 50m
1 stop
ORD
Chicago O'Hare Intl

Which airlines fly to Chicago?

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

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
Buffalo to Chicago Flights
Fastest flight time
1h 55m
Cheapest price
207 C$
Toronto to Chicago Flights
Fastest flight time
1h 47m
Cheapest price
236 C$
Vancouver to Chicago Flights
Fastest flight time
3h 59m
Cheapest price
245 C$
Moncton to Chicago Flights
Fastest flight time
6h 16m
Cheapest price
329 C$
Ottawa to Chicago Flights
Fastest flight time
4h 55m
Cheapest price
338 C$
Regina to Chicago Flights
Fastest flight time
10h 09m
Cheapest price
339 C$
Calgary to Chicago Flights
Fastest flight time
3h 19m
Cheapest price
343 C$
Québec City to Chicago Flights
Fastest flight time
2h 51m
Cheapest price
351 C$
Victoria to Chicago Flights
Fastest flight time
11h 10m
Cheapest price
374 C$
Montreal to Chicago Flights
Fastest flight time
2h 26m
Cheapest price
376 C$
Halifax to Chicago Flights
Fastest flight time
6h 52m
Cheapest price
399 C$
Winnipeg to Chicago Flights
Fastest flight time
4h 04m
Cheapest price
423 C$
Grande Prairie to Chicago Flights
Fastest flight time
10h 50m
Cheapest price
429 C$
Saskatoon to Chicago Flights
Fastest flight time
11h 33m
Cheapest price
442 C$
Kelowna to Chicago Flights
Fastest flight time
8h 56m
Cheapest price
446 C$
London to Chicago Flights
Fastest flight time
9h 36m
Cheapest price
461 C$
Kingston to Chicago Flights
Fastest flight time
5h 28m
Cheapest price
461 C$
St. John's to Chicago Flights
Fastest flight time
10h 47m
Cheapest price
487 C$
Nanaimo to Chicago Flights
Fastest flight time
9h 40m
Cheapest price
536 C$
Saint John to Chicago Flights
Fastest flight time
10h 14m
Cheapest price
615 C$
View more

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