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When is the best time to fly to Chicago?

+45.0%
+30.0%
+15.0%
Base
Price
346 - 481 CAD

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
04 Sep.
Toronto Island airport
1h 45m
MDW
Chicago Midway airport
Porter Airlines
MDW
10 Sep.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
240 CAD
Porter Airlines
Porter Airlines
YTZ
05 Sep.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
17 Sep.
Chicago Midway airport
1h 40m
YTZ
Toronto Island airport
261 CAD
Porter Airlines
Porter Airlines
YTZ
16 Aug.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
18 Aug.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
268 CAD
Porter Airlines
Porter Airlines
YTZ
16 Jul.
Toronto Island airport
1h 45m
MDW
Chicago Midway airport
Porter Airlines
MDW
23 Jul.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
269 CAD
Porter Airlines
Porter Airlines
YTZ
01 Oct.
Toronto Island airport
1h 49m
MDW
Chicago Midway airport
Porter Airlines
MDW
04 Oct.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
269 CAD
Delta
Delta
YYZ
04 Sep.
Toronto Pearson Intl airport
6h 56m
1 Stop
ORD
Chicago O'Hare Intl airport
Delta
ORD
10 Sep.
Chicago O'Hare Intl airport
4h 48m
1 Stop
YYZ
Toronto Pearson Intl airport
278 CAD
United Airlines
United Airlines
YYZ
17 Oct.
Toronto Pearson Intl airport
1h 47m
ORD
Chicago O'Hare Intl airport
United Airlines
ORD
18 Oct.
Chicago O'Hare Intl airport
1h 36m
YYZ
Toronto Pearson Intl airport
319 CAD
Porter Airlines
Porter Airlines
YTZ
04 Sep.
Toronto Island airport
1h 45m
MDW
Chicago Midway airport
Porter Airlines
MDW
10 Sep.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
240 CAD
Air Canada
Air Canada
YYZ
02 Aug.
Toronto Pearson Intl airport
1h 48m
ORD
Chicago O'Hare Intl airport
Air Canada
ORD
04 Aug.
Chicago O'Hare Intl airport
1h 39m
YYZ
Toronto Pearson Intl airport
349 CAD
Porter Airlines
Porter Airlines
YTZ
05 Sep.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
17 Sep.
Chicago Midway airport
1h 40m
YTZ
Toronto Island airport
261 CAD
Porter Airlines
Porter Airlines
YTZ
16 Jul.
Toronto Island airport
1h 45m
MDW
Chicago Midway airport
Porter Airlines
MDW
23 Jul.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
269 CAD
Porter Airlines
Porter Airlines
YTZ
16 Aug.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
18 Aug.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
268 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
Vancouver to Chicago
Fastest flight time
4h 00m
Cheapest price
403 CAD
Montreal to Chicago
Fastest flight time
3h 42m
Cheapest price
319 CAD
Toronto to Chicago
Fastest flight time
1h 45m
Cheapest price
240 CAD
Calgary to Chicago
Fastest flight time
3h 19m
Cheapest price
378 CAD
Québec City to Chicago
Fastest flight time
4h 12m
Cheapest price
351 CAD
Winnipeg to Chicago
Fastest flight time
2h 13m
Cheapest price
498 CAD
Edmonton to Chicago
Fastest flight time
7h 50m
Cheapest price
391 CAD
Halifax to Chicago
Fastest flight time
3h 48m
Cheapest price
397 CAD
Ottawa to Chicago
Fastest flight time
3h 27m
Cheapest price
331 CAD
Saskatoon to Chicago
Fastest flight time
7h 57m
Cheapest price
366 CAD
Buffalo to Chicago
Fastest flight time
1h 45m
Cheapest price
269 CAD
London to Chicago
Fastest flight time
4h 19m
Cheapest price
395 CAD
Victoria to Chicago
Fastest flight time
8h 01m
Cheapest price
473 CAD
Regina to Chicago
Fastest flight time
10h 41m
Cheapest price
635 CAD
View more

Start planning your trip to Chicago