CHI

Find cheap American Airlines flights to Chicago from C$ 141

1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap American Airlines Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from American Airlines to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip American Airlines flight deals to Chicago

Thu, 5 Feb - Sun, 8 Feb
American Airlines Logo
3:45 p.m. - 10:20 p.m.
YYZ
-
ORD
7h 35m1 stop
American Airlines Logo
6:00 a.m. - 11:59 a.m.
ORD
-
YYZ
4h 59m1 stop
C$ 255American Airlines
Thu, 5 Feb - Sun, 8 Feb
American Airlines Logo
3:50 p.m. - 5:50 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
6:05 a.m. - 1:45 p.m.
ORD
-
YUL
6h 40m1 stop
C$ 266American Airlines
Fri, 6 Feb - Sun, 8 Feb
American Airlines Logo
4:44 p.m. - 5:44 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
6:42 a.m. - 3:30 p.m.
ORD
-
YYZ
7h 48m1 stop
C$ 268American Airlines
Thu, 5 Feb - Sun, 8 Feb
American Airlines Logo
7:30 a.m. - 1:59 p.m.
YUL
-
ORD
7h 29m1 stop
American Airlines Logo
6:05 a.m. - 1:45 p.m.
ORD
-
YUL
6h 40m1 stop
C$ 273American Airlines
Thu, 5 Feb - Sun, 8 Feb
American Airlines Logo
3:50 p.m. - 5:50 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
6:05 a.m. - 1:45 p.m.
ORD
-
YUL
6h 40m1 stop
C$ 275American Airlines
Thu, 19 Feb - Mon, 23 Feb
American Airlines Logo
3:45 p.m. - 8:44 p.m.
YYZ
-
ORD
5h 59m1 stop
American Airlines Logo
9:47 a.m. - 12:32 p.m.
ORD
-
YYZ
1h 45mdirect
C$ 277American Airlines
Sun, 1 Feb - Wed, 4 Feb
American Airlines Logo
10:59 a.m. - 4:50 p.m.
YYZ
-
ORD
6h 51m1 stop
American Airlines Logo
9:41 a.m. - 12:34 p.m.
ORD
-
YYZ
1h 53mdirect
C$ 278American Airlines
Thu, 15 Jan - Sun, 25 Jan
American Airlines Logo
6:00 a.m. - 7:15 a.m.
YYZ
-
ORD
2h 15mdirect
American Airlines Logo
8:07 a.m. - 10:53 a.m.
ORD
-
YYZ
1h 46mdirect
C$ 280American Airlines
Sat, 14 Feb - Tue, 17 Feb
American Airlines Logo
7:30 a.m. - 12:07 p.m.
YUL
-
ORD
5h 37m1 stop
American Airlines Logo
11:51 a.m. - 3:10 p.m.
ORD
-
YUL
2h 19mdirect
C$ 281American Airlines
Sat, 24 Jan - Sat, 31 Jan
American Airlines Logo
7:04 p.m. - 8:04 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
1:20 p.m. - 4:03 p.m.
ORD
-
YYZ
1h 43mdirect
C$ 282American Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flightC$ 141
Average price round-tripC$ 482
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly (53% more expensive on average)
Flight from Calgary to Chicago
(price for this month)

When to book flights with American Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with American Airlines

  • Which other airlines fly to Chicago?

    Along with American Airlines, you can also fly to Chicago with Porter Airlines, Porter Airlines, United Airlines and Air Canada.

  • Which airport do American Airlines flights to Chicago fly into?

    American Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

  • Are there any other airlines in oneworld that fly to Chicago?

    Unfortunately, there are no other airlines in oneworld that fly to Chicago.

Top tips for your flights to Chicago with American Airlines

  • High season for flights to Chicago with American Airlines is May and prices are highest at this time. The cheapest month to fly is March.

American Airlines customer reviews

7.2
Good10,000 verified ratings
6.5Food
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
Pros +
  • Flight crew was pleasant enough. (in 437 reviews)
  • Crew was good and mostly attentive (in 1650 reviews)
Cons -
  • Plane was also dirty and I had to whipe down my own area (in 1199 reviews)
Show reviews that mention
Traveler rating:
Sort by:
A
8.0 Very good
Quick and efficient boarding
J
10.0 Wonderful
Good flight
C
8.0 Very good
it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..
J
10.0 Wonderful
I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You
J
8.0 Very good
I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.
A
2.0 Poor
Worst experience in a long time. American sucks!
J
2.0 Poor
Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane
D
10.0 Wonderful
Attendants were pleasant and the flight was smooth and relaxed.
D
10.0 Wonderful
A little late at the start but all worked out well.
J
10.0 Wonderful
It was fine. No drinks nor snacks offered though. I thought that was unusual.
Read more about American Airlines

Everything you need to know for your flight to Chicago

Other airlines flying to Chicago

Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
WestJet flights to Chicago
United Airlines flights to Chicago
Air Canada flights to Chicago
Porter Airlines flights to Chicago