Find cheap flights to Chicago

Wed. 21/8
Wed. 28/8
Any month
Compare vs. momondo |

When is the best time to fly to Chicago?

+45.0%
+30.0%
+15.0%
Base
Price
357 - 489 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
05 Nov.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
MDW
10 Nov.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
238 CAD
Porter Airlines
Porter Airlines
YTZ
12 Dec.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
MDW
16 Dec.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
240 CAD
Porter Airlines
Porter Airlines
YTZ
15 Sep.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
20 Sep.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
242 CAD
Porter Airlines
Porter Airlines
YTZ
10 Sep.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
11 Sep.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
264 CAD
Porter Airlines
Porter Airlines
YTZ
17 Oct.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
20 Oct.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
264 CAD
Porter Airlines
Porter Airlines
YTZ
18 Oct.
Toronto Island airport
1h 45m
MDW
Chicago Midway airport
Porter Airlines
MDW
21 Oct.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
270 CAD
United Airlines
United Airlines
YYZ
25 Oct.
Toronto Pearson Intl airport
1h 47m
ORD
Chicago O'Hare Intl airport
United Airlines
ORD
28 Oct.
Chicago O'Hare Intl airport
1h 36m
YYZ
Toronto Pearson Intl airport
336 CAD
Porter Airlines
Porter Airlines
YTZ
12 Dec.
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
MDW
16 Dec.
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
240 CAD
Porter Airlines
Porter Airlines
YTZ
18 Oct.
Toronto Island airport
1h 45m
MDW
Chicago Midway airport
Porter Airlines
MDW
21 Oct.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
270 CAD
Porter Airlines
Porter Airlines
YTZ
15 Sep.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
20 Sep.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
242 CAD
Porter Airlines
Porter Airlines
YTZ
10 Sep.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
11 Sep.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
264 CAD
Porter Airlines
Porter Airlines
YTZ
17 Oct.
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
MDW
20 Oct.
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
264 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
Fastest flight time
1h 45m
Cheapest price
238 CAD
Montreal to Chicago
Fastest flight time
3h 42m
Cheapest price
281 CAD
Ottawa to Chicago
Fastest flight time
3h 32m
Cheapest price
313 CAD
Buffalo to Chicago
Fastest flight time
1h 50m
Cheapest price
314 CAD
Calgary to Chicago
Fastest flight time
3h 26m
Cheapest price
322 CAD
Québec City to Chicago
Fastest flight time
4h 14m
Cheapest price
333 CAD
Saskatoon to Chicago
Fastest flight time
5h 17m
Cheapest price
370 CAD
Edmonton to Chicago
Fastest flight time
7h 35m
Cheapest price
378 CAD
Vancouver to Chicago
Fastest flight time
3h 59m
Cheapest price
409 CAD
Halifax to Chicago
Fastest flight time
3h 48m
Cheapest price
442 CAD
London to Chicago
Fastest flight time
5h 04m
Cheapest price
457 CAD
Victoria to Chicago
Fastest flight time
7h 00m
Cheapest price
481 CAD
Kelowna to Chicago
Fastest flight time
12h 02m
Cheapest price
485 CAD
Winnipeg to Chicago
Fastest flight time
2h 24m
Cheapest price
493 CAD
St. John's to Chicago
Fastest flight time
9h 47m
Cheapest price
626 CAD
Saint John to Chicago
Fastest flight time
7h 32m
Cheapest price
655 CAD
Grande Prairie to Chicago
Fastest flight time
10h 54m
Cheapest price
715 CAD
Fort McMurray to Chicago
Fastest flight time
7h 54m
Cheapest price
794 CAD
Regina to Chicago
Fastest flight time
12h 56m
Cheapest price
887 CAD
Moncton to Chicago
Fastest flight time
11h 12m
Cheapest price
889 CAD
View more

Start planning your trip to Chicago