Cheap flights from Toronto Pearson Intl Airport to Chicago

Round-trip
1 adult
Economy
From?
To?
Tue 9/21
Tue 9/28

Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Toronto Pearson Intl to Chicago.
View current United States travel restrictions

Flight information for Toronto Pearson Intl Airport to Chicago
(YYZ to CHI)

Find info about flight duration, direct flights, and airports for your flight from Toronto Pearson Intl Airport to Chicago
Best Price Found$247The best flight deal from Toronto Pearson Intl Airport to Chicago found on momondo in the last 72 hours is $247
Fastest flight time2h 00mThe fastest flight from Toronto Pearson Intl Airport to Chicago takes 2h 00m
Direct flightsSatDirect flights go from Toronto Pearson Intl Airport to Chicago on Saturday. The only airline offering direct flights is United Airlines.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Toronto Pearson Intl Airport to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago?

April

The cheapest time of year to fly to Chicago from Toronto Pearson Intl Airport is April. Most expensive is October

What is the cheapest airline that flies to Chicago from Toronto Pearson Intl Airport?

Air Canada

Air Canada, American Airlines, and Delta are the most popular carriers operating from Toronto Pearson Intl Airport to Chicago

How far in advance should you book Toronto Pearson Intl Airport to Chicago flights?

38 days before

The cheapest time to buy a flight from Toronto Pearson Intl Airport to Chicago is approximately 38 days to departure


Easily compare round-trip flights from Toronto Pearson Intl Airport to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Toronto Pearson Intl Airport to Chicago by changing tabs
Multiple Airlines
Nov 4
YYZ4:05 amToronto Pearson Intl
16h 58m
1 stop
ORD9:03 pmChicago O'Hare Intl
Nov 7
ORD2:10 pmChicago O'Hare Intl
28h 15m
1 stop
YYZ6:25 pmToronto Pearson Intl
Multiple Airlines
Nov 2
YYZ3:55 amToronto Pearson Intl
10h 43m
1 stop
ORD2:38 pmChicago O'Hare Intl
Nov 4
ORD3:45 amChicago O'Hare Intl
15h 40m
1 stop
YYZ7:25 pmToronto Pearson Intl
Multiple Airlines
Nov 7
YYZ3:15 amToronto Pearson Intl
16h 48m
1 stop
ORD8:03 pmChicago O'Hare Intl
Nov 8
ORD2:45 amChicago O'Hare Intl
15h 40m
1 stop
YYZ6:25 pmToronto Pearson Intl
Multiple Airlines
Nov 2
YYZ2:15 amToronto Pearson Intl
18h 48m
2 stops
ORD9:03 pmChicago O'Hare Intl
Nov 4
ORD3:45 amChicago O'Hare Intl
15h 40m
1 stop
YYZ7:25 pmToronto Pearson Intl
Multiple Airlines
Nov 4
YYZ4:05 amToronto Pearson Intl
31h 04m
2 stops
ORD11:09 amChicago O'Hare Intl
Nov 7
ORD2:10 pmChicago O'Hare Intl
28h 15m
1 stop
YYZ6:25 pmToronto Pearson Intl
Multiple Airlines
Dec 3
YYZ2:55 pmToronto Pearson Intl
28h 37m
1 stop
ORD7:32 pmChicago O'Hare Intl
Dec 6
ORD12:52 amChicago O'Hare Intl
17h 33m
1 stop
YYZ6:25 pmToronto Pearson Intl

Find the cheapest one-way flights from Toronto Pearson Intl Airport to Chicago

If you're looking for one-way flights from Toronto Pearson Intl Airport to Chicago, view some of our deals below provided by Air Canada and American Airlines
Air Canada
Jan 18
YYZ6:10 amToronto Pearson Intl
8h 22m
2 stops
ORD2:32 pmChicago O'Hare Intl
Air Canada
Nov 7
YYZ9:10 amToronto Pearson Intl
8h 22m
2 stops
ORD5:32 pmChicago O'Hare Intl
Air Canada
Jan 18
YYZ9:10 amToronto Pearson Intl
6h 29m
1 stop
ORD3:39 pmChicago O'Hare Intl

Search last-minute flights to Chicago from Toronto Pearson Intl Airport

Find and compare flight prices for your last-minute flight from Toronto Pearson Intl Airport to Chicago
Air Canada
Sep 26
YYZ8:00 amToronto Pearson Intl
1h 50m
ORD9:50 amChicago O'Hare Intl
Oct 4
ORD8:45 amChicago O'Hare Intl
5h 36m
1 stop
YYZ2:21 pmToronto Pearson Intl
Air Canada
Sep 26
YYZ4:35 amToronto Pearson Intl
1h 50m
ORD6:25 amChicago O'Hare Intl
Oct 15
ORD5:30 pmChicago O'Hare Intl
9h 26m
1 stop
YYZ2:56 amToronto Pearson Intl
Delta
Sep 26
YYZ12:00 pmToronto Pearson Intl
3h 23m
1 stop
ORD3:23 pmChicago O'Hare Intl
Oct 15
ORD3:00 amChicago O'Hare Intl
8h 04m
1 stop
YYZ11:04 amToronto Pearson Intl
Air Canada
Sep 21
YYZ12:00 pmToronto Pearson Intl
4h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 28
ORD8:45 amChicago O'Hare Intl
5h 36m
1 stop
YYZ2:21 pmToronto Pearson Intl
Air Canada
Sep 22
YYZ11:00 amToronto Pearson Intl
5h 43m
1 stop
ORD4:43 pmChicago O'Hare Intl
Sep 29
ORD8:45 amChicago O'Hare Intl
5h 36m
1 stop
YYZ2:21 pmToronto Pearson Intl
Air Canada
Sep 21
YYZ6:55 amToronto Pearson Intl
1h 50m
ORD8:45 amChicago O'Hare Intl
Sep 28
ORD5:00 amChicago O'Hare Intl
7h 21m
1 stop
YYZ12:21 pmToronto Pearson Intl

Best airlines flying from Toronto Pearson Intl Airport to Chicago

Compare and see reviews for airlines that fly from Toronto Pearson Intl Airport to Chicago with momondo
AirlineRatingFree CancellationPrice
American Airlines
PriceFrom $150
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.1

Entertainment

6.8

Food

Reviews

Flight attendant for first class is definitely not a morning person. Oh and the WiFi DID NOT WORK!

1 / 10
Air Canada
PriceFrom $179
Free Cancellation
Rating
7.5
7.8

Boarding

7.3

Comfort

8.1

Crew

7.3

Entertainment

5.9

Food

Reviews

The food selection has been better in the past but due to Covid it is understandable. This particular flight did not have any entertainment and the Air Canada App did not work to access movies.

1 / 10
United Airlines
PriceFrom $198
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.

1 / 10
Delta
PriceFrom $225
Free Cancellation
Rating
8.3
8.3

Boarding

8.5

Comfort

8.4

Crew

8.1

Entertainment

8.1

Food

Reviews

Great

1 / 10

  • Are airlines flying from Toronto Pearson Intl to Chicago offering flexible cancellation due to COVID-19?

    To ease the stress of booking flights, some of our airline partners flying from Toronto Pearson Intl to Chicago are responding to the global pandemic. The following airlines may have a flexible cancellation policy to help accommodate travelers: American Airlines, Air Canada, and United Airlines.

  • How far is Toronto Pearson Intl to Chicago by plane?

    The straight-line distance from Toronto Pearson Intl to Chicago is 424.4 mi. Typically, this will take 1h 42m by plane in normal conditions.


Can I fly to Chicago from Toronto Pearson Intl right now?

Information is based on travel restrictions from Toronto Pearson Intl to Chicago

Most visitors from Toronto Pearson Intl need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Toronto Pearson Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Toronto Pearson Intl are not required to quarantine after entering Chicago.

Can I fly back to Toronto Pearson Intl from Chicago?

Returning to Toronto Pearson Intl from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Toronto Pearson Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Toronto Pearson Intl.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.

Alternative routes for Toronto Pearson Intl Airport to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Toronto to Chicago Flights
Fastest flight time1h 41m
Cheapest price$204