EN
Languages
USD
Top currencies
All currencies
Help
Within the United States +1-833-896-0077 English: 24/7
Global Access Number +1-646-362-8606 English: 24/7
App
Download the App for Free

Cheap Flights from Toronto to Chicago

  • Toronto Chicago

    Fri, Feb 7 - Sun, Feb 9

    From US$141.16
  • Toronto Chicago

    Fri, Feb 7 - Sun, Feb 9

    From US$186.32
  • Toronto Chicago

    Fri, Feb 7 - Sun, Feb 9

    From US$194.13
  • Toronto Chicago

    Sat, Jan 4 - Thu, Jan 9

    From US$214.86
  • Toronto Chicago

    Fri, Jan 10 - Sun, Jan 12

    From US$237.72
  • Toronto Chicago

    Sun, May 17 - Tue, May 19

    From US$268.68

Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)

Toronto to Chicago Flight Information

Below are some common questions asked about this flight route:

Best time to book Toronto to Chicago flights

Generally the best time to book Toronto to Chicago flights is two months in advance. And the cheapest days to fly are Tuesdays, Wednesdays, and Saturdays. Sunday is the most expensive.

How many direct flights from Toronto to Chicago?

There are 196 direct flights from Toronto to Chicago.

What is the most popular airline for non-stop flights from Toronto to Chicago?

Air Canada provides 27.000002 of the non-stop flights between Toronto and Chicago.

Airlines flying this route:
Airports in Toronto:
Airports in Chicago:
Average duration of direct flights: 1h53m

Toronto to Chicago Flight Schedule

Flight info. Departure
Arrival
Route Weekly Schedule
11:09 YYZ 12:02 ORD
Toronto to Chicago SMTWTFS Search
07:44 YYZ 08:50 ORD
Toronto to Chicago SMTWTFS Search
11:45 YYZ 12:37 ORD
Toronto to Chicago ----TFS Search
17:40 YYZ 18:38 ORD
Toronto to Chicago SMT---- Search
13:40 YYZ 14:22 ORD
Toronto to Chicago -MTW--S Search
AC509
14:55 YYZ 15:44 ORD
Toronto to Chicago SMTWTFS Search
AC501
06:40 YYZ 07:29 ORD
Toronto to Chicago SMTWTFS Search
08:15 YYZ 09:19 ORD
Toronto to Chicago SMTWTFS Search
AC505
10:10 YYZ 10:59 ORD
Toronto to Chicago SMTWTFS Search
AC513
18:15 YYZ 19:04 ORD
Toronto to Chicago SMTWTFS Search
AC511
16:40 YYZ 17:29 ORD
Toronto to Chicago SMTWTFS Search
AC507
12:55 YYZ 13:44 ORD
Toronto to Chicago SMTWTFS Search
AC515
20:55 YYZ 21:44 ORD
Toronto to Chicago SMTWTFS Search
18:05 YTZ 18:55 MDW
Toronto to Chicago -MT---- Search
AY4106
15:13 YYZ 16:13 ORD
Toronto to Chicago ------S Search
NH7763
ANA
08:16 YYZ 09:03 ORD
Toronto to Chicago SMTWTFS Search
NH7383
ANA
13:51 YYZ 14:43 ORD
Toronto to Chicago SMTWTFS Search
08:25 YTZ 09:15 MDW
Toronto to Chicago -MT---- Search
08:15 YYZ 09:14 ORD
Toronto to Chicago SMTWTFS Search
AC5588
13:50 YYZ 14:39 ORD
Toronto to Chicago ---WTFS Search

Toronto to O'Hare International Airport (ORD)

07:45, Feb 7 - 07:56, Feb 9
AA | American Airlines
2h 17m
YYZ - ORD
Nonstop
US$142
Round-trip from
Search
21:18, Feb 7 - 07:56, Feb 9
UA | United Airlines
2h 5m
YYZ - ORD
Nonstop
US$196
Round-trip from
Search
12:55, May 17 - 19:35, May 19
AC | Air Canada
1h 49m
YYZ - ORD
Nonstop
US$271
Round-trip from
Search
09:45, Feb 7 - 07:56, Feb 9
DL | Delta Air Lines
4h 20m
YYZ - ORD
1 stop
US$188
Round-trip from
Search
17:59, Dec 29 - 17:50, Jan 5
WS | Westjet
5h 8m
YYZ - ORD
1 stop
US$473
Round-trip from
Search

Toronto to Midway International Airport (MDW)

09:45, Dec 24 - 11:20, Dec 30
PD | Porter Airlines
1h 50m
YTZ - MDW
Nonstop
US$218
Round-trip from
Search
06:14, Jan 30 - 07:56, Feb 2
DL | Delta Air Lines
6h 39m
YYZ - MDW
1 stop
US$195
Round-trip from
Search
09:45, Jan 4 - 06:30, Jan 9
PD | Porter Airlines
1h 50m
YTZ - MDW
1 stop
US$217
Round-trip from
Search
11:58, Feb 12 - 09:18, Feb 18
DL | Delta Air Lines
5h 22m
YYZ - MDW
2 stop
US$195
Round-trip from
Search

Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)

Roundtrip vs One-Way Flights from Toronto to Chicago

There is usually no major price difference between buying a roundtrip flight versus a one-way flight. Increased flexibility is the main benefit when it comes to buying a one-way flight from Toronto to Chicago. However, booking a roundtrip flight is a simpler process. You can compare roundtrip and one-way flights by using our flight comparison tool.

Nonstop vs Connecting Flights from Toronto to Chicago

The average price for connecting flights from Toronto to Chicago is USD 197.46.The average price for nonstop flights from Toronto to Chicago is USD 207.24.

Travel from Toronto to Chicago

Chicago attracts thousands of visitors every year for both business and pleasure. Planning a trip from Toronto to Chicago is easy when you use Trip.com to help you make travel arrangements. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online.

A Trip to Remember

Make your journey from Toronto to Chicago a trip to remember when you use Trip.com to review city attractions before you arrive. With a preview of what's available at your destination, you can make any necessary reservations in advance for the best travel experience possible.