United Airlines Toronto to Chicago Flights

Return flight: Chicago – Toronto

Cheapflightsplus.com will find cheap United Airlines flights from Toronto to Chicago. Compare airline ticket prices and book air tickets starting from $72 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of United Airlines, arrivals and departure details below.

Find Cheap Airfare Toronto (ON) — Chicago (IL) by United Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in june: one-way - $72, two-way – $123.
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Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:00 am — 10:53 am
10:00 am — 10:53 am UA8278 United Airlines
Toronto — Chicago
1h 53m
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from$72
11:00 am — 12:03 pm
11:00 am — 12:03 pm UA5676 United Airlines
Toronto — Chicago
2h 3m
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from$150
11:00 am — 12:01 pm
11:00 am — 12:01 pm UA5650 United Airlines
Toronto — Chicago
2h 1m
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from$177
11:00 am — 12:01 pm
11:00 am — 12:01 pm UA5563 United Airlines
Toronto — Chicago
2h 1m
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from$231
12:00 pm — 12:53 pm
12:00 pm — 12:53 pm UA8694 United Airlines
Toronto — Chicago
1h 53m
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from$93
1:00 pm — 2:01 pm
1:00 pm — 2:01 pm UA3605 United Airlines
Toronto — Chicago
2h 1m
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from$72
1:00 pm — 2:01 pm
1:00 pm — 2:01 pm UA3499 United Airlines
Toronto — Chicago
2h 1m
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from$149
2:10 pm — 3:04 pm
2:10 pm — 3:04 pm UA8307 United Airlines
Toronto — Chicago
1h 54m
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from$72
2:45 pm — 3:48 pm
2:45 pm — 3:48 pm UA3616 United Airlines
Toronto — Chicago
2h 3m
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from$93
2:45 pm — 3:50 pm
2:45 pm — 3:50 pm UA3404 United Airlines
Toronto — Chicago
2h 5m
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from$147
2:45 pm — 3:48 pm
2:45 pm — 3:48 pm UA5258 United Airlines
Toronto — Chicago
2h 3m
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from$153
4:30 pm — 5:23 pm
4:30 pm — 5:23 pm UA8287 United Airlines
Toronto — Chicago
1h 53m
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from$153
5:14 pm — 6:21 pm
5:14 pm — 6:21 pm UA5536 United Airlines
Toronto — Chicago
2h 7m
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from$153
5:15 pm — 6:15 pm
5:15 pm — 6:15 pm UA1371 United Airlines
Toronto — Chicago
2h
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from$88
5:15 pm — 6:12 pm
5:15 pm — 6:12 pm UA2121 United Airlines
Toronto — Chicago
1h 57m
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from$93
6:35 pm — 7:29 pm
6:35 pm — 7:29 pm UA8293 United Airlines
Toronto — Chicago
1h 54m
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from$72
7:00 am — 7:56 am
7:00 am — 7:56 am UA490 United Airlines
Toronto — Chicago
1h 56m
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from$93
8:15 am — 9:08 am
8:15 am — 9:08 am UA8533 United Airlines
Toronto — Chicago
1h 53m
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from$72
9:00 am — 9:55 am
9:00 am — 9:55 am UA1538 United Airlines
Toronto — Chicago
1h 55m
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from$72
9:00 pm — 10:07 pm
9:00 pm — 10:07 pm UA5928 United Airlines
Toronto — Chicago
2h 7m
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from$72
9:00 pm — 10:05 pm
9:00 pm — 10:05 pm UA4808 United Airlines
Toronto — Chicago
2h 5m
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from$88
9:00 pm — 10:05 pm
9:00 pm — 10:05 pm UA3640 United Airlines
Toronto — Chicago
2h 5m
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from$93
10:32 am — 2:55 pm
10:32 am — 12:15 pm UA3648 United Airlines
Toronto — Newark
1h 5m stop
1:20 pm — 2:55 pm UA2053 United Airlines
Newark — Chicago
5h 23m
including layover
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from$84
11:30 am — 7:57 pm
11:30 am — 1:05 pm UA8664 United Airlines
Toronto — Newark
5h 10m stop
6:15 pm — 7:57 pm UA254 United Airlines
Newark — Chicago
9h 27m
including layover
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from$100
11:30 am — 9:28 pm
11:30 am — 1:07 pm UA8664 United Airlines
Toronto — Newark
6h 39m stop
7:46 pm — 9:28 pm UA546 United Airlines
Newark — Chicago
10h 58m
including layover
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from$101
12:10 pm — 7:55 pm
12:10 pm — 1:38 pm UA8670 United Airlines
Toronto — Washington D.C.
5h 9m stop
6:47 pm — 7:55 pm UA2304 United Airlines
Washington D.C. — Chicago
8h 45m
including layover
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from$84
12:45 pm — 8:11 pm
12:45 pm — 2:28 pm UA3649 United Airlines
Toronto — Newark
4h 2m stop
6:30 pm — 8:11 pm UA254 United Airlines
Newark — Chicago
8h 26m
including layover
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from$84
1:55 pm — 9:26 pm
1:55 pm — 3:34 pm UA8660 United Airlines
Toronto — Newark
4h 9m stop
8:30 pm — 10:12 pm UA546 United Airlines
Newark — Chicago
8h 31m
including layover
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from$85
3:00 pm — 8:10 pm
3:00 pm — 4:50 pm UA3705 United Airlines
Toronto — Newark
1h 39m stop
6:29 pm — 8:10 pm UA2310 United Airlines
Newark — Chicago
6h 10m
including layover
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from$101
3:00 pm — 9:26 pm
3:00 pm — 4:48 pm UA3705 United Airlines
Toronto — Newark
2h 55m stop
8:30 pm — 10:12 pm UA546 United Airlines
Newark — Chicago
7h 26m
including layover
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from$108
4:30 pm — 9:16 pm
4:30 pm — 6:02 pm UA8548 United Airlines
Toronto — Washington D.C.
1h 56m stop
8:00 pm — 9:16 pm UA2218 United Airlines
Washington D.C. — Chicago
5h 46m
including layover
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from$84
4:30 pm — 8:15 pm
4:30 pm — 6:03 pm UA8548 United Airlines
Toronto — Washington D.C.
56m stop
7:11 pm — 8:27 pm UA1193 United Airlines
Washington D.C. — Chicago
4h 45m
including layover
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from$84
6:00 pm — 11:30 pm
6:00 pm — 7:48 pm UA3460 United Airlines
Toronto — Newark
1h 54m stop
9:55 pm — 11:37 pm UA1308 United Airlines
Newark — Chicago
6h 30m
including layover
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from$84
7:30 am — 1:07 pm
7:30 am — 9:04 am UA3435 United Airlines
Toronto — Newark
2h 16m stop
11:37 am — 1:14 pm UA1875 United Airlines
Newark — Chicago
6h 37m
including layover
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from$84
7:47 pm — 11:15 pm
7:47 pm — 9:25 pm UA3466 United Airlines
Toronto — Washington D.C.
45m stop
10:18 pm — 11:30 pm UA1738 United Airlines
Washington D.C. — Chicago
4h 28m
including layover
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from$84
8:10 am — 4:52 pm
8:10 am — 9:37 am UA8271 United Airlines
Toronto — Washington D.C.
6h 2m stop
3:39 pm — 4:52 pm UA1057 United Airlines
Washington D.C. — Chicago
9h 42m
including layover
Find flight
from$96
*Departure and arrival times are local. Last updated on 06/03/2025

Flight Information

There are 22 flights by United Airlines from Toronto to Chicago every week with departures from Pearson International, Toronto Island, Buttonville Municipal. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:00 am to 9:20 am. Nonstop flight is 1h 53m. The time difference between Toronto and Chicago is 1h.

  • The fastest flight 1h 53m
  • Average flight time 2h 1m
  • The earliest flight 10:00 am
  • The latest flight 9:20 am
  • Distance 436 ml

The cheapest months for traveling to Chicago are october (from 96 $), september (from 97 $), july (from 118 $).

The most expensive and popular months are november (from 256 $), february (from 220 $), january (from 204 $).

The cheapest flight by United Airlines that our users were able to find is $72. This airfare is economy class on one-way UA3605 flight for October 7, 2025 leaving Pearson International in Toronto at 1:00 pm, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides United Airlines there are other 10 airline carriers between Toronto and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Toronto to Chicago.

Nonstop flights

There are 39 direct flights every day from Toronto. Airlines and fares are below:

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

  • from $101
    Find
  • from $129
    Find
  • F8 - Freedom Airlines
    from $120
    Find
  • AS - Alaska Airlines
    from $218
    Find
  • AV - Avianca
    from $408
    Find
  • SY - Sun Country Airlines
    from $162
    Find
  • WS - WestJet
    from $132
    Find
  • AM - Aeromexico
    from $498
    Find
  • LX - SWISS International Air Lines
    from $3152
    Find
  • TS - Air Transat
    from $146
    Find
See more connecting flights

How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
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  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

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