Find cheap flights to Chicago

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Seattle (SEA)
Chicago (CHI)
Fri. 10/4
Fri. 17/4
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Cheapest flights to Chicago airports

Find the cheapest flights to these Chicago airports from your nearest city or airport
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When is the best time to fly to Chicago?

What is the cheapest month to fly to Chicago?

Travelling from most locations, it is best to book your flight to Chicago during the month of February for the best deal, although there are other times of the year which offer great deals as well.

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 from airports in Canada to Chicago found recently by users on momondo
Quickest
Cheapest
Porter Airlines
12 Jul.
YTZ
Toronto Island
1h 47m
MDW
Chicago Midway
15 Jul.
MDW
Chicago Midway
1h 42m
YTZ
Toronto Island
Multiple Airlines
15 Jun.
YYZ
Toronto Pearson Intl
1h 53m
ORD
Chicago O'Hare Intl
16 Jun.
ORD
Chicago O'Hare Intl
1h 39m
YYZ
Toronto Pearson Intl
Delta
14 Apr.
YYZ
Toronto Pearson Intl
3h 29m
1 stop
ORD
Chicago O'Hare Intl
17 Apr.
ORD
Chicago O'Hare Intl
3h 17m
1 stop
YYZ
Toronto Pearson Intl
Porter Airlines
17 Jun.
YTZ
Toronto Island
1h 47m
MDW
Chicago Midway
18 Jul.
MDW
Chicago Midway
1h 42m
YTZ
Toronto Island
Multiple Airlines
13 May
YYZ
Toronto Pearson Intl
2h 07m
ORD
Chicago O'Hare Intl
16 May
ORD
Chicago O'Hare Intl
6h 15m
1 stop
YYZ
Toronto Pearson Intl
Delta
11 May
YYZ
Toronto Pearson Intl
3h 19m
1 stop
MDW
Chicago Midway
17 May
MDW
Chicago Midway
5h 42m
1 stop
YYZ
Toronto Pearson Intl

Find the cheapest one-way flights to Chicago

If you're looking for one-way flights to Chicago, view some of our deals below provided by Delta and Porter Airlines
Quickest
Cheapest
Delta
2 May
YYZ
Toronto Pearson Intl
8h 52m
2 stops
ORD
Chicago O'Hare Intl
Multiple Airlines
22 Jun.
YUL
Montreal Pierre Elliott Trudeau Intl
19h 21m
2 stops
ORD
Chicago O'Hare Intl
Porter Airlines
6 Jun.
YUL
Montreal Pierre Elliott Trudeau Intl
5h 17m
1 stop
MDW
Chicago Midway

Which airlines fly to Chicago?

Here you can see a selection of the most popular and cheapest airlines for flights to Chicago

Airports near Chicago

Below you will find all the airports in Chicago along with their distance from the city centre

Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration
Buffalo to Chicago Flights
Fastest flight time
4h 28m
Cheapest price
149 C$
Toronto to Chicago Flights
Fastest flight time
1h 47m
Cheapest price
202 C$
Calgary to Chicago Flights
Fastest flight time
3h 25m
Cheapest price
243 C$
Ottawa to Chicago Flights
Fastest flight time
2h 08m
Cheapest price
285 C$
Montreal to Chicago Flights
Fastest flight time
2h 25m
Cheapest price
286 C$
Vancouver to Chicago Flights
Fastest flight time
3h 59m
Cheapest price
309 C$
Saskatoon to Chicago Flights
Fastest flight time
9h 43m
Cheapest price
318 C$
Edmonton to Chicago Flights
Fastest flight time
5h 46m
Cheapest price
327 C$
Winnipeg to Chicago Flights
Fastest flight time
2h 29m
Cheapest price
348 C$
Québec City to Chicago Flights
Fastest flight time
2h 51m
Cheapest price
351 C$
Halifax to Chicago Flights
Fastest flight time
7h 35m
Cheapest price
386 C$
Victoria to Chicago Flights
Fastest flight time
7h 58m
Cheapest price
407 C$
Regina to Chicago Flights
Fastest flight time
10h 19m
Cheapest price
463 C$
London to Chicago Flights
Fastest flight time
9h 24m
Cheapest price
477 C$
Moncton to Chicago Flights
Fastest flight time
7h 53m
Cheapest price
477 C$
Kingston to Chicago Flights
Fastest flight time
4h 38m
Cheapest price
485 C$
Kelowna to Chicago Flights
Fastest flight time
10h 24m
Cheapest price
526 C$
St. John's to Chicago Flights
Fastest flight time
10h 47m
Cheapest price
542 C$
Grande Prairie to Chicago Flights
Fastest flight time
12h 05m
Cheapest price
551 C$
Deer Lake to Chicago Flights
Fastest flight time
8h 54m
Cheapest price
599 C$
View more

Start planning your trip to Chicago

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