Find cheap flights to Chicago

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When is the best time to fly to Chicago?

550 C$
480 C$
410 C$
344 C$
Price
344 C$ - 489 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
American Airlines
American Airlines
10 Feb.
YYZ
Toronto Pearson Intl airport
2h 17m
ORD
Chicago O'Hare Intl airport
American Airlines
13 Feb.
ORD
Chicago O'Hare Intl airport
5h 07m
1 Stop
YYZ
Toronto Pearson Intl airport
254 C$
Porter Airlines
Porter Airlines
20 Jan.
YTZ
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Porter Airlines
24 Jan.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
259 C$
Porter Airlines
Porter Airlines
01 Mar.
YTZ
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
31 Mar.
MDW
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
263 C$
Porter Airlines
Porter Airlines
10 Feb.
YTZ
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Porter Airlines
13 Feb.
MDW
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
268 C$
Delta
Delta
21 Jan.
YYZ
Toronto Pearson Intl airport
4h 58m
1 Stop
ORD
Chicago O'Hare Intl airport
Delta
29 Jan.
ORD
Chicago O'Hare Intl airport
1h 43m
YYZ
Toronto Pearson Intl airport
272 C$
Porter Airlines
Porter Airlines
13 Jan.
YTZ
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Porter Airlines
16 Jan.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
281 C$
Air Canada
Air Canada
22 Mar.
YYZ
Toronto Pearson Intl airport
1h 50m
ORD
Chicago O'Hare Intl airport
Air Canada
27 Mar.
ORD
Chicago O'Hare Intl airport
1h 36m
YYZ
Toronto Pearson Intl airport
313 C$
Porter Airlines
Porter Airlines
01 Mar.
YTZ
Toronto Island airport
1h 50m
MDW
Chicago Midway airport
Porter Airlines
31 Mar.
MDW
Chicago Midway airport
1h 37m
YTZ
Toronto Island airport
263 C$
Porter Airlines
Porter Airlines
20 Jan.
YTZ
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Porter Airlines
24 Jan.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
259 C$
United Airlines
United Airlines
10 Mar.
YYZ
Toronto Pearson Intl airport
1h 53m
ORD
Chicago O'Hare Intl airport
United Airlines
14 Mar.
ORD
Chicago O'Hare Intl airport
1h 35m
YYZ
Toronto Pearson Intl airport
288 C$
Porter Airlines
Porter Airlines
13 Jan.
YTZ
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Porter Airlines
16 Jan.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
281 C$
Porter Airlines
Porter Airlines
10 Jan.
YTZ
Toronto Island airport
1h 53m
MDW
Chicago Midway airport
Porter Airlines
17 Jan.
MDW
Chicago Midway airport
1h 35m
YTZ
Toronto Island airport
289 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
Toronto to Chicago Flights
Fastest flight time
1h 47m
Cheapest price
254 C$
Buffalo to Chicago Flights
Fastest flight time
1h 47m
Cheapest price
283 C$
Ottawa to Chicago Flights
Fastest flight time
2h 11m
Cheapest price
318 C$
Montreal to Chicago Flights
Fastest flight time
3h 45m
Cheapest price
326 C$
Calgary to Chicago Flights
Fastest flight time
3h 19m
Cheapest price
349 C$
Winnipeg to Chicago Flights
Fastest flight time
2h 27m
Cheapest price
358 C$
Edmonton to Chicago Flights
Fastest flight time
5h 58m
Cheapest price
396 C$
Saskatoon to Chicago Flights
Fastest flight time
6h 12m
Cheapest price
407 C$
London to Chicago Flights
Fastest flight time
4h 45m
Cheapest price
408 C$
Vancouver to Chicago Flights
Fastest flight time
3h 58m
Cheapest price
415 C$
Québec City to Chicago Flights
Fastest flight time
4h 12m
Cheapest price
423 C$
Halifax to Chicago Flights
Fastest flight time
3h 34m
Cheapest price
439 C$
Kelowna to Chicago Flights
Fastest flight time
12h 17m
Cheapest price
533 C$
Victoria to Chicago Flights
Fastest flight time
7h 03m
Cheapest price
539 C$
Regina to Chicago Flights
Fastest flight time
10h 35m
Cheapest price
554 C$
Deer Lake to Chicago Flights
Fastest flight time
8h 20m
Cheapest price
558 C$
Kingston to Chicago Flights
Fastest flight time
4h 44m
Cheapest price
597 C$
St. John's to Chicago Flights
Fastest flight time
6h 35m
Cheapest price
633 C$
Moncton to Chicago Flights
Fastest flight time
6h 15m
Cheapest price
671 C$
Grande Prairie to Chicago Flights
Fastest flight time
8h 50m
Cheapest price
687 C$
View more

Start planning your trip to Chicago