Find cheap flights to Chicago

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When is the best time to fly to Chicago?

480 C$
440 C$
390 C$
339 C$
Price
339 C$ - 483 C$

When is the best time to fly to Chicago?

From most locations, the cheapest flights to Chicago can be found during the month of February; however great deals can be found at other times.

When is the best time to book flights to Chicago?

On average, from most locations, when planning your trip to Chicago, try to book your flight in the region of 60 days in advance for the cheapest prices.

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 Monday 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
07 Feb.
YTZ
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
10 Feb.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
252 C$
American Airlines
American Airlines
11 Feb.
YYZ
Toronto Pearson Intl airport
2h 17m
ORD
Chicago O'Hare Intl airport
American Airlines
31 Mar.
ORD
Chicago O'Hare Intl airport
3h 48m
1 Stop
YYZ
Toronto Pearson Intl airport
253 C$
Porter Airlines
Porter Airlines
05 Jun.
YTZ
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
07 Jun.
MDW
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
269 C$
Porter Airlines
Porter Airlines
28 Mar.
YTZ
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
01 Apr.
MDW
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
272 C$
Porter Airlines
Porter Airlines
04 May
YTZ
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
11 May
MDW
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
276 C$
Delta
Delta
08 Feb.
YYZ
Toronto Pearson Intl airport
6h 36m
1 Stop
MDW
Chicago Midway airport
Delta
11 Feb.
MDW
Chicago Midway airport
3h 25m
1 Stop
YYZ
Toronto Pearson Intl airport
282 C$
Porter Airlines
Porter Airlines
07 Feb.
YTZ
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
10 Feb.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
252 C$
Porter Airlines
Porter Airlines
28 Mar.
YTZ
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
01 Apr.
MDW
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
272 C$
United Airlines
United Airlines
28 Feb.
YYZ
Toronto Pearson Intl airport
1h 53m
ORD
Chicago O'Hare Intl airport
United Airlines
01 Mar.
ORD
Chicago O'Hare Intl airport
1h 35m
YYZ
Toronto Pearson Intl airport
328 C$
Porter Airlines
Porter Airlines
05 Jun.
YTZ
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
07 Jun.
MDW
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
269 C$
Porter Airlines
Porter Airlines
04 May
YTZ
Toronto Island airport
1h 47m
MDW
Chicago Midway airport
Porter Airlines
11 May
MDW
Chicago Midway airport
1h 42m
YTZ
Toronto Island airport
276 C$
Interjet
Interjet
05 Jun.
YYZ
Toronto Pearson Intl airport
1h 55m
ORD
Chicago O'Hare Intl airport
Interjet
07 Jun.
ORD
Chicago O'Hare Intl airport
1h 39m
YYZ
Toronto Pearson Intl airport
329 C$

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
Calgary to Chicago Flights
Fastest flight time
3h 19m
Cheapest price
213 C$
Buffalo to Chicago Flights
Fastest flight time
1h 49m
Cheapest price
251 C$
Toronto to Chicago Flights
Fastest flight time
1h 45m
Cheapest price
252 C$
London to Chicago Flights
Fastest flight time
4h 50m
Cheapest price
257 C$
Montreal to Chicago Flights
Fastest flight time
3h 42m
Cheapest price
298 C$
Ottawa to Chicago Flights
Fastest flight time
3h 40m
Cheapest price
320 C$
Saskatoon to Chicago Flights
Fastest flight time
5h 13m
Cheapest price
345 C$
Québec City to Chicago Flights
Fastest flight time
4h 12m
Cheapest price
383 C$
Vancouver to Chicago Flights
Fastest flight time
3h 58m
Cheapest price
426 C$
Edmonton to Chicago Flights
Fastest flight time
5h 59m
Cheapest price
444 C$
Halifax to Chicago Flights
Fastest flight time
3h 34m
Cheapest price
457 C$
Moncton to Chicago Flights
Fastest flight time
5h 55m
Cheapest price
465 C$
Winnipeg to Chicago Flights
Fastest flight time
2h 13m
Cheapest price
478 C$
Kelowna to Chicago Flights
Fastest flight time
7h 00m
Cheapest price
509 C$
Fort McMurray to Chicago Flights
Fastest flight time
12h 14m
Cheapest price
525 C$
Victoria to Chicago Flights
Fastest flight time
6h 05m
Cheapest price
533 C$
St. John's to Chicago Flights
Fastest flight time
10h 47m
Cheapest price
550 C$
Regina to Chicago Flights
Fastest flight time
8h 04m
Cheapest price
589 C$
Saint John to Chicago Flights
Fastest flight time
5h 40m
Cheapest price
590 C$
Deer Lake to Chicago Flights
Fastest flight time
7h 29m
Cheapest price
608 C$
View more

Start planning your trip to Chicago