Cheap Flights from Toronto, ON to Chicago, IL from $84
Return flight: Chicago – Toronto
On Cheapflightsplus.com you will find 9 direct and 56 connecting flights from Toronto to Chicago. You can compare airfare deals from 9 airlines and multiple travel sites from $84, book and save on cheap plane tickets and last minute offers. Also check out YTO-CHI flight schedule to find best flight time, convenient departure and arrival airports.
Find One-Way and Round-Trip Toronto to Chicago Flight Deals
To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights».
To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight.
Cheapest flights in November: $84 (one-way), $144 (round-trip).
Direct flights
Check prices for return flight
Best Flights from Toronto to Chicago Today
Take a look at the list of non stop flights and flights with layovers from Toronto to Chicago with the lowest price of $84. The fastest direct flight takes 1h 49m and the fastest connecting – 5h 7m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $84 | 15:35 Toronto Toronto Island | 16:24 Chicago Midway | 1h 49m | Porter Airlines | PD2393 |
| from $98 | 14:10 Toronto Pearson International | 15:04 Chicago O'Hare International | 1h 54m | United Airlines | UA8307 |
| from $98 | 18:35 Toronto Pearson International | 19:29 Chicago O'Hare International | 1h 54m | United Airlines | UA8293 |
| from $98 | 13:00 Toronto Pearson International | 14:01 Chicago O'Hare International | 2h 1m | United Airlines | UA3605 |
| from $126 | 15:35 Toronto Toronto Island | 16:24 Chicago Midway | 1h 49m | Air Transat | TS7314 |
| from $127 | 12:20 Toronto Pearson International | 13:13 Chicago O'Hare International | 1h 53m | United Airlines | UA8694 |
| from $127 | 17:15 Toronto Pearson International | 18:15 Chicago O'Hare International | 2h 0m | United Airlines | UA1371 |
| from $203 | 21:00 Toronto Pearson International | 22:05 Chicago O'Hare International | 2h 5m | United Airlines | UA3640 |
| from $209 | 11:00 Toronto Pearson International | 12:01 Chicago O'Hare International | 2h 1m | United Airlines | UA3499 |
| from $114 | 21:10 Toronto Pearson International | 07:38+1 день Chicago O'Hare International | 11h 28m layover 7h 12m - Newark | United Airlines | UA8266 UA2164 |
| from $137 | 08:10 Toronto Pearson International | 14:33 Chicago O'Hare International | 7h 23m layover 3h 43m - Washington D.C. | United Airlines | UA8271 UA2331 |
| from $209 | 09:45 Toronto Toronto Island | 20:00 Chicago O'Hare International | 11h 15m layover 7h 15m - New York | Porter Airlines | PD2127 NK1179 |
| from $213 | 14:50 Toronto Pearson International | 20:00 Chicago O'Hare International | 6h 10m layover 2h 0m - New York | Porter Airlines | PD605 NK1179 |
| from $213 | 07:15 Toronto Pearson International | 20:00 Chicago O'Hare International | 13h 45m layover 9h 35m - New York | Porter Airlines | PD603 NK1179 |
| from $226 | 12:15 Toronto Pearson International | 16:52 Chicago O'Hare International | 5h 37m layover 1h 57m - Washington D.C. | United Airlines | UA8670 UA1057 |
| from $219 | 07:00 Toronto Toronto Island | 20:00 Chicago O'Hare International | 14h 0m layover 2h 57m - Ottawa 6h 0m - New York | Porter Airlines | PD2205 PD2335 NK1179 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 26, 2025
Flight Schedule Toronto (Ontario) to Chicago (Illinois)
Full flight schedule will help you in detecting at what time planes fly from Toronto to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
| Departure | Arrival | Flight Details | Flight Duration | Price |
|---|---|---|---|---|
|
11:00 — 12:01
|
11:00 — 12:01
UA3499
United Airlines
Toronto — Chicago
|
2h 1m |
Find flight
from$209 |
|
|
12:20 — 13:13
|
12:20 — 13:13
UA8694
United Airlines
Toronto — Chicago
|
1h 53m |
Find flight
from$127 |
|
|
13:00 — 14:01
|
13:00 — 14:01
UA3605
United Airlines
Toronto — Chicago
|
2h 1m |
Find flight
from$98 |
|
|
14:10 — 15:04
|
14:10 — 15:04
UA8307
United Airlines
Toronto — Chicago
|
1h 54m |
Find flight
from$98 |
|
|
15:35 — 16:24
|
15:35 — 16:24
PD2393
Porter Airlines
Toronto — Chicago
|
1h 49m |
Find flight
from$84 |
|
|
15:35 — 16:24
|
15:35 — 16:24
TS7314
Air Transat
Toronto — Chicago
|
1h 49m |
Find flight
from$126 |
|
|
17:15 — 18:15
|
17:15 — 18:15
UA1371
United Airlines
Toronto — Chicago
|
2h |
Find flight
from$127 |
|
|
18:35 — 19:29
|
18:35 — 19:29
UA8293
United Airlines
Toronto — Chicago
|
1h 54m |
Find flight
from$98 |
|
|
21:00 — 22:05
|
21:00 — 22:05
UA3640
United Airlines
Toronto — Chicago
|
2h 5m |
Find flight
from$203 |
|
|
06:15 — 14:19
|
06:15 — 08:37
WS8135
WestJet
Toronto — Atlanta
4h 34m stop
13:11 — 14:19
WS7273
WestJet
Atlanta — Chicago
|
9h 4m including layover |
Find flight
from$259 |
|
|
06:30 — 12:02
|
06:30 — 07:45
WS6353
WestJet
Toronto — Minneapolis
2h 50m stop
10:35 — 12:02
WS7997
WestJet
Minneapolis — Chicago
|
6h 32m including layover |
Find flight
from$288 |
|
|
07:15 — 20:00
|
07:15 — 08:55
PD603
Porter Airlines
Toronto — New York
9h 35m stop
18:30 — 20:00
NK1179
Spirit Airlines
New York — Chicago
|
13h 45m including layover |
Find flight
from$213 |
|
|
08:10 — 14:33
|
08:10 — 09:39
UA8271
United Airlines
Toronto — Washington D.C.
3h 43m stop
13:20 — 14:33
UA2331
United Airlines
Washington D.C. — Chicago
|
7h 23m including layover |
Find flight
from$137 |
|
|
09:45 — 20:00
|
09:45 — 11:15
PD2127
Porter Airlines
Toronto — New York
7h 15m stop
18:30 — 20:00
NK1179
Spirit Airlines
New York — Chicago
|
11h 15m including layover |
Find flight
from$209 |
|
|
12:15 — 16:52
|
12:10 — 13:41
UA8670
United Airlines
Toronto — Washington D.C.
1h 57m stop
15:35 — 16:48
UA1057
United Airlines
Washington D.C. — Chicago
|
5h 37m including layover |
Find flight
from$226 |
|
|
13:20 — 18:49
|
13:20 — 15:44
WS7106
WestJet
Toronto — Atlanta
1h 45m stop
17:29 — 18:49
WS6651
WestJet
Atlanta — Chicago
|
6h 29m including layover |
Find flight
from$239 |
|
|
14:50 — 20:00
|
14:50 — 16:30
PD605
Porter Airlines
Toronto — New York
2h stop
18:30 — 20:00
NK1179
Spirit Airlines
New York — Chicago
|
6h 10m including layover |
Find flight
from$213 |
|
|
16:00 — 15:06
+1 day
|
16:00 — 18:54
WS1224
WestJet
Toronto — Orlando
18h 15m stop
18:20 — 20:17
F93853
Frontier Airlines
Orlando — Chicago
|
24h 6m including layover |
Find flight
from$428 |
|
|
18:05 — 13:50
+1 day
|
18:05 — 06:15
AY5992
Finnair
Toronto — London
4h 50m stop
11:05 — 13:50
AY5535
Finnair
London — Chicago
|
20h 45m including layover |
Find flight
from$3463 |
|
|
20:05 — 06:03
+1 day
|
20:05 — 21:55
PD655
Porter Airlines
Toronto — Las Vegas
2h 39m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
10h 58m including layover |
Find flight
from$259 |
|
|
20:05 — 06:03
+1 day
|
20:05 — 21:58
TS7230
Air Transat
Toronto — Las Vegas
2h 39m stop
00:34 — 06:03
NK1053
Spirit Airlines
Las Vegas — Chicago
|
10h 58m including layover |
Find flight
from$282 |
|
|
21:10 — 07:38
+1 day
|
21:10 — 22:47
UA8266
United Airlines
Toronto — Newark
7h 12m stop
06:00 — 07:38
UA2164
United Airlines
Newark — Chicago
|
11h 28m including layover |
Find flight
from$114 |
|
|
07:00 — 20:00
|
07:00 — 07:58
PD2205
Porter Airlines
Toronto — Ottawa
2h 57m stop
11:00 — 12:30
PD2335
Porter Airlines
Ottawa — New York
6h stop
18:30 — 20:00
NK1179
Spirit Airlines
New York — Chicago
|
14h including layover |
Find flight
from$219 |
|
|
08:30 — 23:53
|
08:30 — 10:00
PD2123
Porter Airlines
Toronto — Newark
7h 23m stop
17:23 — 20:35
NK1218
Spirit Airlines
Newark — Miami
55m stop
21:30 — 23:53
NK1219
Spirit Airlines
Miami — Chicago
|
16h 23m including layover |
Find flight
from$566 |
|
|
09:30 — 15:31
+1 day
|
09:30 — 10:28
PD2219
Porter Airlines
Toronto — Ottawa
5h 57m stop
16:25 — 19:44
PD505
Porter Airlines
Ottawa — Orlando
17h 39m stop
13:23 — 15:31
NK1369
Spirit Airlines
Orlando — Chicago
|
31h 1m including layover |
Find flight
from$401 |
|
|
11:40 — 09:41
+1 day
|
11:40 — 12:53
SY1918
Sun Country Airlines
Toronto — Minneapolis
6h 57m stop
19:50 — 23:08
G4246
Allegiant Air
Minneapolis — Fletcher
9h 52m stop
09:00 — 09:41
G41848
Allegiant Air
Fletcher — Chicago
|
23h 1m including layover |
Find flight
from$355 |
|
|
16:00 — 11:41
+1 day
|
16:00 — 18:55
WS1224
WestJet
Toronto — Orlando
2h 4m stop
20:59 — 23:11
F93311
Frontier Airlines
Orlando — Denver
9h 4m stop
08:15 — 11:41
F92210
Frontier Airlines
Denver — Chicago
|
20h 41m including layover |
Find flight
from$750 |
|
|
17:15 — 07:04
+1 day
|
17:15 — 18:45
PD2141
Porter Airlines
Toronto — Newark
3h 15m stop
22:00 — 00:32
NK1212
Spirit Airlines
Newark — Atlanta
5h 28m stop
06:00 — 07:04
NK1116
Spirit Airlines
Atlanta — Chicago
|
14h 49m including layover |
Find flight
from$566 |
|
|
22:25 — 17:39
+1 day
|
22:25 — 00:44
WS679
WestJet
Toronto — Calgary
9h 46m stop
10:30 — 14:07
WS1610
WestJet
Calgary — Minneapolis
1h 58m stop
16:05 — 17:39
WS8011
WestJet
Minneapolis — Chicago
|
20h 14m including layover |
Find flight
from$960 |
|
|
22:30 — 13:06
+1 day
|
22:30 — 00:13
WS535
WestJet
Toronto — Winnipeg
8h 22m stop
08:35 — 10:05
WS5407
WestJet
Winnipeg — Minneapolis
1h 22m stop
11:27 — 13:06
WS8687
WestJet
Minneapolis — Chicago
|
15h 36m including layover |
Find flight
from$972 |
|
|
23:05 — 21:16
+1 day
|
23:05 — 00:27
WS598
WestJet
Toronto — Montreal
9h 33m stop
10:00 — 14:23
WS2902
WestJet
Montreal — Punta Cana
2h 45m stop
17:08 — 21:16
F981
Frontier Airlines
Punta Cana — Chicago
|
23h 11m including layover |
Find flight
from$521 |
|
|
23:15 — 08:07
+2 days
|
23:15 — 00:22
WS374
WestJet
Toronto — Ottawa
16h 3m stop
16:25 — 19:44
PD505
Porter Airlines
Ottawa — Orlando
10h 21m stop
06:05 — 08:07
F93043
Frontier Airlines
Orlando — Chicago
|
33h 52m including layover |
Find flight
from$673 |
|
*Departure and arrival times - local. Updated on July 26, 2025
Flight Information
Below we will explain in detail what the flights cost on the destination from Toronto to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Toronto and Chicago is 701 miles. Time difference between the cities is 1h. Airplanes depart 06:04 to 23:50 from 3 Toronto airports and arrive 06:04 to 23:50 to 7 Chicago airports. Average flight time is 1h 54m.
- The fastest flight 1h 49m
- Average flight time 1h 54m
- The earliest flight 06:04
- The latest flight 23:50
- Distance 436 ml
The cheapest months to travel to Chicago are october (from 84 $), september (from 99 $), july (from 103 $).
The most expensive months are february (from 224 $), january (from 208 $), november (from 183 $).
What is the lowest airfare Toronto to Chicago?
The cheapest plane ticket found by our users is $84. This airfare is for economy class on one-way PD2393 flight by Porter Airlines for October 7, 2025 which leaves Toronto Island in Toronto at 15:35 am and arrives at Chicago Midway at 16:24.
Economy class
$84
Business class
?
First class
?
Popular Airlines on the Route
The flight Toronto — Chicago is served by 9 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Air Canada - 1 departures per week at the price of from $ 1029 . And the most expensive tickets are offered by Finnair airline - from $ 3496.
Direct flights
There are 9 nonstop flights on the route. The fastest direct flight is PD2393 by Porter Airlines takes 1h 49m and the cheapest is PD2393 by Porter Airlines for $84.
- from $84Find
- from $98Find
- TS - Air Transatfrom $126Find
See more direct flights
Connecting Flights
There are 56 flights with layovers on the route. The fastest connecting flight is UA3633 by United Airlines takes 5h 7m and the cheapest is PD2393 by Porter Airlines for $114.
- from $1029Find
- from $209Find
- from $114Find
- F8 - Freedom Airlinesfrom $257Find
- AV - Aviancafrom $1131Find
- SY - Sun Country Airlinesfrom $355Find
- AY - Finnairfrom $3463Find
- WS - WestJetfrom $239Find
- TS - Air Transatfrom $251Find
See more connecting flights
Airports
You can fly from Toronto to Chicago from 3 airports (Buttonville Municipal, Toronto Island, Pearson International).
Toronto airports
- Buttonville Municipal-YKZFind
- Toronto Island-YTZfrom $84Find
- Pearson International-YYZfrom $98Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Toronto by 9 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top International Destinations from Toronto
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $75Find
- from $55Find
- from $64Find
- from $54Find
- from $72Find
- from $78Find
- from $73Find
- from $65Find
- from $56Find
- from $66Find
How to book a plane 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.
- Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
- Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
- 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.
To find a plane ticket, please select dates.