CHI

Find cheap American Airlines flights to Chicago from C$ 163

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, 9 Apr - Sat, 11 Apr
American Airlines Logo
12:30 p.m. - 2:10 p.m.
YUL
-
ORD
2h 40mdirect
American Airlines Logo
7:15 a.m. - 1:52 p.m.
ORD
-
YUL
5h 37m
1 stop
C$ 264American Airlines
Thu, 26 Mar - Mon, 30 Mar
American Airlines Logo
7:12 a.m. - 2:16 p.m.
YUL
-
ORD
8h 04m
1 stop
American Airlines Logo
11:44 a.m. - 2:58 p.m.
ORD
-
YUL
2h 14mdirect
C$ 272American Airlines
Tue, 24 Mar - Fri, 27 Mar
American Airlines Logo
1:10 p.m. - 2:10 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
6:40 p.m. - 9:29 p.m.
ORD
-
YYZ
1h 49mdirect
C$ 285American Airlines
Sun, 29 Mar - Sun, 5 Apr
American Airlines Logo
6:00 a.m. - 7:15 a.m.
YYZ
-
ORD
2h 15mdirect
American Airlines Logo
1:22 p.m. - 4:03 p.m.
ORD
-
YYZ
1h 41mdirect
C$ 286American Airlines
Sat, 11 Apr - Mon, 13 Apr
American Airlines Logo
12:30 p.m. - 2:10 p.m.
YUL
-
ORD
2h 40mdirect
American Airlines Logo
8:18 a.m. - 11:44 a.m.
ORD
-
YUL
2h 26mdirect
C$ 291American Airlines
Fri, 27 Mar - Tue, 31 Mar
American Airlines Logo
6:00 a.m. - 7:15 a.m.
YYZ
-
ORD
2h 15mdirect
American Airlines Logo
10:10 a.m. - 7:04 p.m.
ORD
-
YYZ
7h 54m
1 stop
C$ 298American Airlines
Tue, 31 Mar - Sat, 4 Apr
American Airlines Logo
3:45 p.m. - 5:45 p.m.
YUL
-
ORD
3h 00mdirect
American Airlines Logo
3:16 p.m. - 10:48 p.m.
ORD
-
YUL
6h 32m
1 stop
C$ 298American Airlines
Sat, 7 Mar - Sat, 14 Mar
American Airlines Logo
6:17 p.m. - 7:17 p.m.
YYZ
-
ORD
2h 00mdirect
American Airlines Logo
7:10 a.m. - 6:29 p.m.
ORD
-
YYZ
10h 19m
1 stop
C$ 300American Airlines
Tue, 24 Mar - Fri, 27 Mar
American Airlines Logo
5:22 p.m. - 9:24 p.m.
YYZ
-
ORD
5h 02m
1 stop
American Airlines Logo
6:40 p.m. - 9:29 p.m.
ORD
-
YYZ
1h 49mdirect
C$ 305American Airlines
Wed, 15 Apr - Mon, 20 Apr
American Airlines Logo
2:32 p.m. - 11:54 p.m.
YUL
-
ORD
10h 22m
1 stop
American Airlines Logo
8:18 a.m. - 11:44 a.m.
ORD
-
YUL
2h 26mdirect
C$ 305American Airlines
Useful Info

Good to know

Low seasonDecember
Cheapest flightC$ 163
Average price round-tripC$ 668
Good deal round-tripC$ 568
Most popular time to fly (26% more expensive on average)
Flight from Montreal to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less

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

  • Is American Airlines cheaper than other airlines flying to Chicago?

    American Airlines is the cheapest airline flying to Chicago with an average return price of C$ 668. Flights to Chicago with United Airlines cost C$ 691 on average, while WestJet cost C$ 810.

  • Which other airlines fly to Chicago?

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

  • How much is a flight to Chicago with American Airlines?

    On average, American Airlines flights to Chicago cost C$ 668 for a round-trip.

  • 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

  • The cheapest flight to Chicago with American Airlines found on KAYAK in the last 2 weeks departed from Québec City and cost C$ 384.
  • High season for flights to Chicago with American Airlines is July and prices are highest at this time. The cheapest month to fly is January.

American Airlines customer reviews

7.2
Good10,000 verified ratings
7.5Boarding
7.2Comfort
6.4Food
8.0Crew
6.9Entertainment
Traveler rating:
Sort by:
J
4.0 Mediocre
The flight to PHl was delayed by 3 hours.
R
10.0 Wonderful
Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.
A
4.0 Mediocre
The smell from the bathroom kept wafting through the cabin. It made people sick.
A
8.0 Very good
More comfortable seats. Better snacks.
M
6.0 Okay
The flight was really crowded. Flight attendants were just ok.
R
10.0 Wonderful
Better food Better choices
K
10.0 Wonderful
Great!
S
2.0 Poor
Never flying AA again, two delays, lost baggage.
J
2.0 Poor
Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?
S
4.0 Mediocre
Didn't get a seat assignment until the last minute even though i picked a seat.
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.
Air Canada flights to Chicago
WestJet flights to Chicago
United Airlines flights to Chicago
Porter Airlines flights to Chicago