Which other airlines fly to Chicago?

Along with American Airlines, you can also fly to Chicago with United Airlines, Southwest, Allegiant Air, United Airlines, Frontier, Frontier, Delta, Alaska Airlines, Contour, Denver Air Connection, Contour and Allegiant Air.

How much is a flight to Chicago with American Airlines?

On average, American Airlines flights to Chicago cost $337 one-way.

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?

The only other oneworld airline flying to Chicago is Alaska Airlines.

American Airlines flights to Chicago (CHI) from $78

Flight Deals

Cheap American Airlines Flight Deals to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip American Airlines flight deals to Chicago

Sat, Jul 11 - Wed, Jul 15

1:50 pm - 3:46 pm

JFK

ORD

2h 56mnonstop

4:26 pm - 8:00 pm

ORD

JFK

2h 34mnonstop

$119American Airlines

Sat, Jun 6 - Sat, Jun 13

9:59 am - 11:47 am

JFK

ORD

2h 48mnonstop

4:44 pm - 8:15 pm

ORD

JFK

2h 31mnonstop

$153American Airlines

Wed, Jul 15 - Sat, Jul 18

12:01 pm - 2:02 pm

BOS

ORD

3h 01mnonstop

8:30 pm - 11:59 pm

ORD

BOS

2h 29mnonstop

$157American Airlines

Fri, May 1 - Fri, May 8

4:34 pm - 6:51 pm

BOS

ORD

3h 17mnonstop

8:56 pm - 12:25 am

ORD

BOS

2h 29mnonstop

$158American Airlines

Sat, May 23 - Wed, May 27

6:36 pm - 9:00 pm

BOS

ORD

3h 24mnonstop

7:00 am - 10:29 am

ORD

BOS

2h 29mnonstop

$160American Airlines

Thu, Apr 30 - Sun, May 3

8:03 am - 10:12 am

BOS

ORD

3h 09mnonstop

6:00 am - 9:27 am

ORD

BOS

2h 27mnonstop

$167American Airlines

Sat, May 16 - Sat, May 23

6:30 am - 8:44 am

BOS

ORD

3h 14mnonstop

5:20 pm - 8:53 pm

ORD

BOS

2h 33mnonstop

$168American Airlines

Sat, May 16 - Sat, May 23

6:52 pm - 9:04 pm

BOS

ORD

3h 12mnonstop

8:45 pm - 12:15 am

ORD

BOS

2h 30mnonstop

$169American Airlines

Wed, Apr 29 - Wed, Apr 29

12:10 pm - 2:13 pm

JFK

ORD

3h 03mnonstop

4:36 pm - 8:03 pm

ORD

JFK

2h 27mnonstop

$172American Airlines

Thu, May 7 - Thu, May 7

5:59 am - 8:01 am

LGA

ORD

3h 02mnonstop

10:02 am - 1:17 pm

ORD

LGA

2h 15mnonstop

$172American Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$78
Average price round-trip	$279

Best time to beat the crowds with an average 6% drop in price.

Most popular time to fly and prices are also 3% lower on average.

Flight from Boston to Chicago O'Hare Airport

(price for this month)

When to book flights with American Airlines to Chicago

Average price per month

Flight prices as travel date approaches

Which other airlines fly to Chicago?
Along with American Airlines, you can also fly to Chicago with United Airlines, Southwest, Allegiant Air, United Airlines, Frontier, Frontier, Delta, Alaska Airlines, Contour, Denver Air Connection, Contour and Allegiant Air.
How much is a flight to Chicago with American Airlines?
On average, American Airlines flights to Chicago cost $337 one-way.
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?
The only other oneworld airline flying to Chicago is Alaska Airlines.

The cheapest flight to Chicago with American Airlines found on KAYAK in the last 2 weeks departed from Manchester and cost $132.
If you’re intending to fly with American Airlines, book your flight to Chicago at least 2 weeks before departure to ensure a below-average price.
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.

7.1

Good10,000 verified ratings

7.5Boarding

6.4Food

7.2Comfort

6.9Entertainment

7.9Crew

4.0 Mediocre

Jana, Apr 2026

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

6.0 Okay

Adam, Apr 2026

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

8.0 Very good

Jane, Apr 2026

Poor at assisting passengers with disabilities.

2.0 Poor

Serena, Apr 2026

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

2.0 Poor

Anonymous, Apr 2026

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

2.0 Poor

Kathryn, Apr 2026

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

10.0 Wonderful

Michael, Apr 2026

It was perfect

2.0 Poor

Ian, Apr 2026

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

6.0 Okay

Mary, Apr 2026

Overall experience was good.

2.0 Poor

Mary, Apr 2026

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

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Cheap American Airlines Flight Deals to Chicago

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When to book flights with American Airlines to Chicago

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 United Airlines, Southwest, Allegiant Air, United Airlines, Frontier, Frontier, Delta, Alaska Airlines, Contour, Denver Air Connection, Contour and Allegiant Air.

How much is a flight to Chicago with American Airlines?

On average, American Airlines flights to Chicago cost $337 one-way.

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?

The only other oneworld airline flying to Chicago is Alaska Airlines.

Top tips for your flights to Chicago with American Airlines

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Everything you need to know for your flight to Chicago

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