Find cheap flights to Chicago

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When is the best time to fly to Chicago?

512 CAD
459 CAD
406 CAD
353 CAD
Price
353 - 484 CAD

When is the best time to fly to Chicago?

Most travellers find the cheapest round-trip airfare to Chicago when booking during the month of February.

When is the best time to book flights to Chicago?

Most flyers found that booking flight tickets 60 days in advance of their planned departure date is, on average, the best time to get cheap flights to Chicago.

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

Most of our users find that booking their departure to Chicago on a Wednesday is the cheapest. Conversely, departing on a Sunday seems to be the most expensive.

What is the cheapest time of day to fly to Chicago?

In general, when looking for the cheapest flight to Chicago, our data indicates that noon flights are the most cost-effective. evening flights tend to be the most expensive.


Chicago flight deals found on momondo

Check out some of the best fares to Chicago found recently by users on momondo
Quickest
Cheapest
Porter Airlines
Porter Airlines
YTZ
08 Dec.
Toronto Island airport
1h 48m
MDW
Chicago Midway airport
Porter Airlines
MDW
14 Dec.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
236 CAD
Porter Airlines
Porter Airlines
YTZ
15 Nov.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
18 Nov.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
240 CAD
Major Airline
Major Airline
YTZ
12 Feb.
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Major Airline
MDW
16 Feb.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
268 CAD
Major Airline
Major Airline
YTZ
26 Mar.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Major Airline
MDW
21 Apr.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
268 CAD
Porter Airlines
Porter Airlines
YTZ
15 Nov.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
17 Nov.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
271 CAD
Delta
Delta
YYZ
06 Nov.
Toronto Pearson Intl airport
3h 39m
1 Stop
ORD
Chicago O'Hare Intl airport
Delta
ORD
26 Nov.
Chicago O'Hare Intl airport
3h 09m
1 Stop
YYZ
Toronto Pearson Intl airport
283 CAD
Porter Airlines
Porter Airlines
YTZ
15 Nov.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
18 Nov.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
240 CAD
Porter Airlines
Porter Airlines
YTZ
08 Dec.
Toronto Island airport
1h 48m
MDW
Chicago Midway airport
Porter Airlines
MDW
14 Dec.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
236 CAD
Porter Airlines
Porter Airlines
YTZ
20 Nov.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
MDW
26 Nov.
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
287 CAD
Major Airline
Major Airline
YTZ
26 Mar.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Major Airline
MDW
21 Apr.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
268 CAD
Porter Airlines
Porter Airlines
YTZ
13 Dec.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
MDW
15 Dec.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
283 CAD
Porter Airlines
Porter Airlines
YTZ
15 Nov.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
17 Nov.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
271 CAD

Airports near Chicago

Below you will find all the airports in Chicago along with their distance from the city centre
Chicago Midway
13 km from city centre
Chicago O'Hare Intl
24 km from city centre
Chicago Greater Rockford
126 km from 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 time
1h 47m
Cheapest price
236 CAD
Buffalo to Chicago Flights
Fastest flight time
1h 47m
Cheapest price
243 CAD
Montreal to Chicago Flights
Fastest flight time
3h 48m
Cheapest price
279 CAD
Ottawa to Chicago Flights
Fastest flight time
3h 40m
Cheapest price
281 CAD
Québec City to Chicago Flights
Fastest flight time
4h 20m
Cheapest price
337 CAD
Winnipeg to Chicago Flights
Fastest flight time
2h 13m
Cheapest price
343 CAD
Calgary to Chicago Flights
Fastest flight time
3h 19m
Cheapest price
371 CAD
Vancouver to Chicago Flights
Fastest flight time
3h 59m
Cheapest price
408 CAD
Halifax to Chicago Flights
Fastest flight time
6h 12m
Cheapest price
415 CAD
Saskatoon to Chicago Flights
Fastest flight time
5h 17m
Cheapest price
416 CAD
Victoria to Chicago Flights
Fastest flight time
8h 45m
Cheapest price
440 CAD
Edmonton to Chicago Flights
Fastest flight time
5h 59m
Cheapest price
444 CAD
Regina to Chicago Flights
Fastest flight time
10h 50m
Cheapest price
469 CAD
Moncton to Chicago Flights
Fastest flight time
6h 15m
Cheapest price
497 CAD
Saint John to Chicago Flights
Fastest flight time
6h 05m
Cheapest price
567 CAD
St. John's to Chicago Flights
Fastest flight time
11h 09m
Cheapest price
588 CAD
Deer Lake to Chicago Flights
Fastest flight time
8h 00m
Cheapest price
685 CAD
Grande Prairie to Chicago Flights
Fastest flight time
9h 59m
Cheapest price
687 CAD
Kelowna to Chicago Flights
Fastest flight time
9h 37m
Cheapest price
688 CAD
London to Chicago Flights
Fastest flight time
3h 48m
Cheapest price
806 CAD
View more

Start planning your trip to Chicago