Travelers have found it’s best to book a flight 38 days in advance to save up to 90% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Region of Ontario to Illinois 1-2 weeks in advance for as low as $337, or $489 for flights within the next 24 hours.
Flights from Region of Ontario to Illinois lean towards being more expensive in September. Prices are generally better when you fly from Region of Ontario to Illinois in April, with the cheapest ticket starting at $193.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Region of Ontario to Illinois as you normally would.
Fly from
Fly to
Budget
$210 - $414
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Mon 7/29
Nonstop1h 47m
Chicago Midway
Sat 8/3
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 6/27
Nonstop1h 47m
Chicago Midway
Thu 7/4
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 6/19
Nonstop1h 57m
Chicago O'Hare Intl
Wed 6/26
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 6/14
1 stop7h 04m
Chicago O'Hare Intl
Mon 6/17
1 stop8h 25m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 9/30
Nonstop1h 56m
Chicago O'Hare Intl
Sat 10/12
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 7/2
Nonstop1h 56m
Chicago O'Hare Intl
Mon 7/8
1 stop5h 57m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 6/18
Nonstop1h 55m
Chicago O'Hare Intl
Fri 6/21
1 stop5h 29m
Montreal Pierre Elliott Trudeau IntlChicago O'Hare Intl
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Mon 7/1
1 stop4h 21m
Chicago O'Hare Intl
Mon 7/8
1 stop4h 59m
Montreal Pierre Elliott Trudeau IntlChicago O'Hare Intl
YUL - ORD
YULORD
Montreal Pierre Elliott Trudeau Intl
Sun 6/23
1 stop11h 40m
Chicago O'Hare Intl
Thu 6/27
1 stop13h 36m
No data available for this route at this time. Please check back soon.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
12%of flight departures | Early morningMidnight to 6 am |
---|---|
34%of flight departures | Morning6 am to noon |
45%of flight departures | AfternoonNoon to 6 pm |
9%of flight departures | Evening6 pm to midnight |
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