
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $175 (SmartFares) |
One-way from | $116 (Kiwi.com) |
Popular in | December |
Cheapest in | July |
Average price | $264 |
Good round-trip deal | $194 or less |
Good one-way deal | $112 or less |
Fly from
Fly to
Route
Depart
Return
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
週四 4/16
9:25 am-10:15 am
Nonstop1h 50m
Chicago Midway
週一 4/20
11:00 am-1:42 pm
Nonstop1h 42m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週六 4/25
5:00 pm-6:52 pm
Nonstop2h 52m
Chicago O'Hare Intl
週一 4/27
7:13 am-10:40 am
Nonstop2h 27m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週三 4/15
5:00 pm-6:52 pm
Nonstop2h 52m
Chicago O'Hare Intl
週一 4/20
6:00 am-1:09 pm
1 stop6h 09m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週五 4/24
6:35 pm-11:43 pm
1 stop6h 08m
Chicago O'Hare Intl
週日 4/26
7:13 am-10:40 am
Nonstop2h 27m
CalgaryChicago
YYC - ORD
YYCORD
Calgary
週五 4/17
1:27 pm-12:30 am
1 stop10h 03m
Chicago O'Hare Intl
週一 4/20
10:04 pm-1:53 pm
1 stop16h 49m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
週四 6/4
8:50 am-9:50 am
Nonstop2h 00m
Chicago O'Hare Intl
週二 6/9
7:09 am-9:54 am
Nonstop1h 45m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週五 4/10
6:35 pm-11:43 pm
1 stop6h 08m
Chicago O'Hare Intl
週五 4/24
2:25 pm-12:13 am
1 stop8h 48m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週二 4/21
11:23 am-4:04 pm
1 stop5h 41m
Chicago O'Hare Intl
週二 4/28
7:00 am-1:09 pm
1 stop5h 09m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
週四 4/9
9:25 am-10:15 am
Nonstop1h 50m
Chicago Midway
週六 4/11
12:55 pm-3:37 pm
Nonstop1h 42m
MontrealChicago
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
週六 4/18
5:00 pm-6:52 pm
Nonstop2h 52m
Chicago O'Hare Intl
週二 4/21
9:00 am-4:10 pm
1 stop6h 10m
Currently, June is the cheapest month in which you can book a flight from Canada to Illinois (average of $83). Flying from Canada to Illinois in July is currently the most expensive (average of $146). 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 Canada to Illinois in the afternoon. Doing so could potentially save you 20% on the flight price compared to flying at noon, which is usually more expensive.
Travelers seeking maximum savings on their Canada to Illinois flight should consider departing on Thursday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CA0 to USIL are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (44 on average).
Crew
Comfort
Overall
Boarding
Entertainment
Food
Reviews
John,Mar 2026
YYZ - PVR
Crew
Comfort
Overall
Boarding
Entertainment
Food
Reviews
John,Mar 2026
YYZ - PVR
Crew
Comfort
Overall
Boarding
Entertainment
Food
Reviews
John,Mar 2026
YYZ - PVR
Crew
Comfort
Overall
Boarding
Entertainment
Food
Reviews
John,Mar 2026
YYZ - PVR
Crew
Comfort
Overall
Boarding
Entertainment
Food
Reviews
John,Mar 2026
YYZ - PVR
Crew
Comfort
Overall
Boarding
Entertainment
Food
Reviews
John,Mar 2026
YYZ - PVR
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$80 | Average$336 | FlexibilityNo cancel fee | On-time52% | |
| Cheapest$83 | Average$381 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$90 | Average$408 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$138 | Average$242 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$167 | Average$373 | FlexibilityNo cancel fee | On-time71% |