
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (Kiwi.com) |
One-way from | $125 (iWofly) |
Popular in | April |
Cheapest in | July |
Average price | $254 |
Good round-trip deal | $183 or less |
Good one-way deal | $102 or less |
Fly from
Fly to
Route
Depart
Return
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
wo 7/1
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
di 7/7
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
za 7/18
8:50 am-9:40 am
Nonstop1h 50m
Chicago Midway
za 7/25
10:25 am-1:05 pm
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
vr 6/19
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
zo 6/21
3:20 pm-6:00 pm
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
vr 5/22
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
wo 6/3
10:15 am-12:55 pm
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
za 6/6
8:45 am-9:35 am
Nonstop1h 50m
Chicago Midway
wo 6/10
10:15 am-12:55 pm
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
vr 6/5
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
zo 6/7
10:15 am-12:55 pm
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
wo 5/27
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
za 5/30
10:30 am-1:10 pm
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
do 5/28
1:00 pm-2:06 pm
Nonstop2h 06m
Chicago O'Hare Intl
ma 6/1
9:15 pm-11:59 pm
Nonstop1h 44m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
wo 6/3
5:15 pm-6:18 pm
Nonstop2h 03m
Chicago O'Hare Intl
wo 6/10
7:09 am-9:54 am
Nonstop1h 45m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
vr 5/29
1:45 pm-2:35 pm
Nonstop1h 50m
Chicago Midway
zo 5/31
3:20 pm-6:00 pm
Nonstop1h 40m
Booking 87 days in advance of your planned departure date is, on average, the best time to get cheap flights from Toronto to Illinois. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Currently, August is the cheapest month in which you can book a flight from Toronto to Illinois (average of $228). Flying from Toronto to Illinois in December is currently the most expensive (average of $935). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
It’s typically best to fly out from Toronto to Illinois in the morning. Doing so could potentially save you 32% on the flight price compared to flying in the evening, which is usually more expensive.
Travelers seeking maximum savings on their Toronto to Illinois flight should consider departing on Tuesday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from YTO to USIL are scheduled on a Thursday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (37 on average).
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
John,Mar 2026
YYZ - PVR
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
John,Mar 2026
YYZ - PVR
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
John,Mar 2026
YYZ - PVR
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
John,Mar 2026
YYZ - PVR
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
John,Mar 2026
YYZ - PVR
Entertainment
Boarding
Food
Crew
Overall
Comfort
Reviews
John,Mar 2026
YYZ - PVR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$350 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$146 | Average$280 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$165 | Average$267 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$189 | Average$292 | FlexibilityNo cancel fee | On-time71% |