Find cheap flights to Chicago

Sun 20/1
Sun 27/1
Any month
Compare vs. momondo |

When is the best time to fly to Chicago?

+60%
+40%
+20%
Base
Price
343 - 503 CAD

Chicago flight deals found on momondo

Check out some of the best fares to Chicago found recently by users on momondo
Quickest
Cheapest
Compagnie importante
Compagnie importante
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Compagnie importante
MDW
23:00
Chicago Midway airport
1h 37min
1:37
+1
YTZ
Toronto Island airport
242 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 37min
1:37
+1
YTZ
Toronto Island airport
247 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 37min
1:37
+1
YTZ
Toronto Island airport
248 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 35min
1:35
+1
YTZ
Toronto Island airport
250 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 35min
1:35
+1
YTZ
Toronto Island airport
258 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 42min
1:42
+1
YTZ
Toronto Island airport
258 CAD
Air Canada
Air Canada
YYZ
0:00
Toronto Pearson Intl airport
1h 48min
0:48
ORD
Chicago O'Hare International airport
Air Canada
ORD
23:00
Chicago O'Hare International airport
1h 35min
1:35
+1
YYZ
Toronto Pearson Intl airport
271 CAD
Air Canada
Air Canada
YYZ
0:00
Toronto Pearson Intl airport
1h 48min
0:48
ORD
Chicago O'Hare International airport
Air Canada
ORD
23:00
Chicago O'Hare International airport
1h 36min
1:36
+1
YYZ
Toronto Pearson Intl airport
286 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 35min
1:35
+1
YTZ
Toronto Island airport
250 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 35min
1:35
+1
YTZ
Toronto Island airport
258 CAD
Compagnie importante
Compagnie importante
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Compagnie importante
MDW
23:00
Chicago Midway airport
1h 37min
1:37
+1
YTZ
Toronto Island airport
242 CAD
Porter Airlines
Porter Airlines
YTZ
0:00
Toronto Island airport
1h 50min
0:50
MDW
Chicago Midway airport
Porter Airlines
MDW
23:00
Chicago Midway airport
1h 37min
1:37
+1
YTZ
Toronto Island airport
247 CAD

Which airlines operate flights to Chicago?

While low cost carriers are the cheapest, don’t forget that the fares often do not include checked baggage, meals, or drinks. Take a look at our estimated additional fees in your search results to get an idea of how much extra you may have to pay.


Airports near Chicago

Below you will find all the airports in Chicago along with the distance from the city centre
Chicago Midway
13 km from city centre
Chicago O'Hare International
24 km from city centre
Chicago Greater Rockford
126 km from city centre

Quick facts about Chicago

Time, currency, and the basics — see the local time and get an idea of how much money you will spend on the basics in Chicago
Local time
Currency
US Dollar
Beer
Domestic Beer (.5 litre)
2.40 CAD
Food
Inexpensive restaurant
20 CAD
Public transport
One-way ticket
3.33 CAD

Start planning your trip to Chicago


Popular routes to Chicago

Most frequently searched flights to Chicago along with the cheapest price and shortest flight duration