How long is the flight to Chicago with American Airlines?

The average American Airlines flight time from Canada to Chicago is 2 hours and 20 minutes.

Which other airlines can I fly to Chicago with?

At the moment, American Airlines, United, Air Canada, Alaska Airlines and Envoy Air all fly to Chicago too.

Is there anywhere else I could fly to with American Airlines?

American Airlines currently also flies to Dallas Fort Worth International, Chicago O'Hare International and Charlotte Douglas.

What's the cheapest month to fly to Chicago with American Airlines?

Although it's difficult to get an accurate idea of when American Airlines flights to Chicago are cheapest, the lowest fares are currently for departures in June .

C$189 American Airlines Flights to Chicago

The best American Airlines flight deals to Chicago

Looking for a last-minute deal or the best direct flight? Find the biggest savings on one-way and round-trip flights to Chicago with American Airlines.

Chicago.C$189 per passenger.Departing Fri, Jun 7.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Calgary on Fri, Jun 7, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$189, select.

Chicago.C$215 per passenger.Departing Tue, Aug 20.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Toronto Pearson International on Tue, Aug 20, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$215, select.

Chicago.C$215 per passenger.Departing Fri, Jul 5.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Toronto Pearson International on Fri, Jul 5, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$215, select.

Chicago.C$224 per passenger.Departing Wed, Sep 11.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Montreal Pierre Elliott Trudeau on Wed, Sep 11, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$224, select.

Chicago.C$261 per passenger.Departing Fri, Oct 4.One-way flight with American Airlines.Outbound indirect flight with American Airlines, departing from Montreal Pierre Elliott Trudeau on Fri, Oct 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$261, select.

Chicago.C$279 per passenger.Departing Fri, Oct 4.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Montreal Pierre Elliott Trudeau on Fri, Oct 4, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$279, select.

Chicago.C$299 per passenger.Departing Thu, May 30.One-way flight with American Airlines.Outbound direct flight with American Airlines departing from Toronto Pearson International on Thu, May 30, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$299, select.

Chicago.C$326 per passenger.Departing Mon, Dec 9.One-way flight with American Airlines.Outbound indirect flight with American Airlines, departing from Calgary on Mon, Dec 9, arriving in Chicago O'Hare International.Price includes taxes and charges.From C$326, select.

Find the cheapest time to fly to Chicago with American Airlines

Flexible on travel dates? Here's when plane tickets are cheapest.

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

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Apr

Find which Chicago airports American Airlines flies to

We were able to find fares for the following Chicago airports. Find the one that works for you.

Flying to Chicago with American Airlines

The things to know before you go.

Cheapest flight found	C$189
Cheapest month to fly	June

How to find cheap flights to Chicago with American Airlines

Looking for cheap plane tickets to Chicago? Here are a few tips on how to find the best price.

Simply hit "search"

We've compared every online travel agent and flight provider out there to find the cheapest American Airlines plane tickets to Chicago. And with us, there are no added fees – what you see is what you pay.

Fly from Calgary

At the moment, the best route to Chicago with American Airlines is from Calgary to Chicago.

Fly in June

The cheapest time to go to Chicago with American Airlines is currently June.

Flex your dates for the best rates

If you're flexible on your departure dates, use Skyscanner's whole month tool to find the cheapest month, and even day, to get flights to Chicago with American Airlines.

Set up a Price Alert

We'll let you know when the price of your flight to Chicago goes up or down so you can book when the time is just right. You're even able to watch specific American Airlines flights.

Book your American Airlines flight to Chicago with extra peace of mind

Find flexible American Airlines flights to Chicago

American Airlines might offer amendable tickets to Chicago, which means you won't lose out if your booking has to be changed or canceled.

Add travel cost protection

Make sure you have the right travel insurance before flying to Chicago. That way you can cover the costs of any unexpected events, such as delays or lost luggage.

Reduce your carbon footprint

To check whether there are any lower-emissions flights available on your route, simply check the “only show flights with lower CO₂ emissions” box when you search for a flight with us.

Flying to Chicago with American Airlines: FAQs

: The average American Airlines flight time from Canada to Chicago is 2 hours and 20 minutes.
: At the moment, American Airlines, United, Air Canada, Alaska Airlines and Envoy Air all fly to Chicago too.
: American Airlines currently also flies to Dallas Fort Worth International, Chicago O'Hare International and Charlotte Douglas.
: Although it's difficult to get an accurate idea of when American Airlines flights to Chicago are cheapest, the lowest fares are currently for departures in June.