Users have found that booking a flight from Region of Ontario to Chicago at least 60 days early can save you up to 45% on average compared to booking a flight this week. If booking 60 days before your flight isn’t an option for you, users have found flights from Region of Ontario to Chicago for as little as C$ 385 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 472 for flights departing within the next 3 days.
The best pricing can be found in the month of June. Prices to Chicago from Region of Ontario average C$ 348. You can even find prices in June for less than C$ 348, as users have found deals to Chicago from as low as C$ 217. The month of March appears to be one of the more expensive times to travel to Chicago from Region of Ontario. Flying in the targeted month can save you up to 14%.
When flying from Region of Ontario to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 42mPorter Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
Nonstop
1h 54mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
8h 53mUnited Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
Nonstop
2h 00mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
5h 16mUnited Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
1 stop
4h 54mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
4h 52mUnited Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
Nonstop
2h 08mChicago O'Hare Intl
Toronto Pearson Intl
Nonstop
1h 35mAmerican Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
Nonstop
2h 06mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
15h 30mAmerican Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
Nonstop
2h 06mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
6h 35mAmerican Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
Nonstop
1h 51mChicago O'Hare Intl
Toronto Pearson Intl
Nonstop
1h 43mAir Canada
Toronto Island
Chicago Midway
Nonstop
1h 50mChicago Midway
Toronto Island
Nonstop
1h 37mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 47mChicago Midway
Toronto Island
Nonstop
1h 42mPorter Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
1 stop
11h 07mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
24h 15mMultiple Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
1 stop
11h 07mChicago O'Hare Intl
Toronto Pearson Intl
2 stops
24h 34mMultiple Airlines
Toronto Pearson Intl
Chicago O'Hare Intl
1 stop
14h 44mChicago O'Hare Intl
Toronto Pearson Intl
1 stop
13h 10mMultiple Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mPorter Airlines
Toronto Island
Chicago Midway
Nonstop
1h 50mPorter Airlines
Toronto Kitchener-Waterloo
Chicago O'Hare Intl
2 stops
17h 55mMultiple Airlines
Some of our airline partners flying from Ontario to Chicago have new flexible policies in place due to COVID-19. Air Canada, Porter Airlines, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.
Yes, there are multiple flights from Region of Ontario to Chicago for under C$ 300. The cheapest flight booked recently is on Porter Airlines for just C$ 270, but on average you can expect to pay C$ 286.
Cheapflights has 20 direct flights from Region of Ontario to Chicago under C$ 200. A good price for a direct flight from Region of Ontario to Chicago is less than C$ 285.
There are currently 20+ open flights from Region of Ontario to Chicago within the next 7 days for less than C$ 300.
Direct flights are available for this route on the following days: Friday, Saturday.
Travellers can expect 5 flights from Region of Ontario to Chicago on average per day.
Morning (6am - Midday) - 100% of flight departures
For as low as C$ 270, Porter Airlines can have you in Chicago from Region of Ontario in 1h 50m. Region of Ontario and Chicago are separated by a distance of 703 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.
The cheapest airline one-way is Porter Airlines, with whom users have recently found tickets for as low as C$ 160. However, be on the lookout for offers from Air Canada and American Airlines, as they are both options that can get you from Region of Ontario to Chicago for a low price.
When deciding which route to take from Region of Ontario to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Toronto Island - Chicago Midway or Toronto Pearson Intl - Chicago Midway as they are the most popular.
Before booking your flight from Region of Ontario to Chicago check out the most popular airlines for this route: Undisclosed Carrier, American Airlines or Air Canada.
No one likes to see their flight delayed. When booking a flight from Region of Ontario to Chicago consider choosing Copa Airlines (86%), Envoy Air (86%) or Republic Airways (85%) as they are the most reliable in getting you off to your destination on time.
On average you can expect to pay C$ 1,646 for a flight from Region of Ontario to Chicago. The cheapest flight overall is C$ 273 while the most popular route, (Toronto Pearson Intl - Chicago O'Hare Intl) is currently priced at C$ 314.
24%of flight departures | Early morningMidnight to 6 am |
---|---|
32%of flight departures | Morning6 am to noon |
35%of flight departures | AfternoonNoon to 6 pm |
9%of flight departures | Evening6 pm to midnight |