Is United Airlines cheaper than other airlines flying to Chicago?

With an average return price of $573, United Airlines is the most expensive airline flying into Chicago. The cheapest airline flying to Chicago is Allegiant Air.

Which other airlines fly to Chicago?

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

How much is a flight to Chicago with United Airlines?

On average, United Airlines flights to Chicago cost $335 for one-way and $573 return.

Which airport do United Airlines flights to Chicago fly into?

United 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 Star Alliance that fly to Chicago?

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

United Airlines flights to Chicago (CHI) from $59

Flights Deals

Cheap United Airlines Flight Deals to Chicago

Here are some of the best deals found on KAYAK recently from United 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.

Round-trip

One-way

Last minute

Direct

Recent round-trip United Airlines flight deals to Chicago

KAYAK's recommended round-trip United Airlines deals departing in the coming months to Chicago.

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

12:30 pm - 2:21 pmBOS-ORD

2h 51mnonstop

7:53 pm - 11:20 pmORD-BOS

2h 27mnonstop

$117United Airlines

Find Deal

Wed, Jun 11 - Mon, Jun 16

6:59 pm - 11:37 pmBOS-ORD

5h 38m1 stop

7:30 am - 10:57 amORD-BOS

2h 27mnonstop

$123United Airlines

Find Deal

Tue, Jul 1 - Tue, Jul 8

7:45 am - 9:43 amBOS-ORD

2h 58mnonstop

7:54 pm - 11:21 pmORD-BOS

2h 27mnonstop

$134United Airlines

Find Deal

Sun, May 25 - Wed, May 28

12:15 pm - 2:12 pmBOS-ORD

2h 57mnonstop

6:25 pm - 9:57 pmORD-BOS

2h 32mnonstop

$135United Airlines

Find Deal

Sat, May 10 - Sat, May 17

6:00 am - 7:57 amBOS-ORD

2h 57mnonstop

9:20 am - 12:48 pmORD-BOS

2h 28mnonstop

$136United Airlines

Find Deal

Sun, May 18 - Wed, May 21

10:25 am - 12:05 pmLGA-ORD

2h 40mnonstop

8:00 pm - 11:18 pmORD-LGA

2h 18mnonstop

$137United Airlines

Find Deal

Tue, May 13 - Tue, May 13

8:20 pm - 10:12 pmBOS-ORD

2h 52mnonstop

6:00 am - 9:26 amORD-BOS

2h 26mnonstop

$137United Airlines

Find Deal

Fri, Jul 11 - Sun, Jul 13

6:00 am - 7:57 amBOS-ORD

2h 57mnonstop

9:20 am - 12:48 pmORD-BOS

2h 28mnonstop

$138United Airlines

Find Deal

Mon, May 19 - Wed, May 21

7:45 am - 9:43 amBOS-ORD

2h 58mnonstop

7:54 pm - 11:21 pmORD-BOS

2h 27mnonstop

$141United Airlines

Find Deal

Sun, May 25 - Tue, May 27

8:30 pm - 10:12 pmEWR-ORD

2h 42mnonstop

6:00 am - 9:13 amORD-EWR

2h 13mnonstop

$147United Airlines

Find Deal

Sat, May 24 - Sun, May 25

Useful Info

Low season	January
High season	July
Cheapest flight	$59
Average price round-trip	$946
Good deal round-trip	$605
Good deal one-way	$342

Best time to beat the crowds with an average 4% drop in price.

Most popular time to fly and prices are also 2% lower on average.

Flight from Boston to Chicago O'Hare Airport

(avg. price over the last 2 weeks)

or less

When to book flights with United Airlines to Chicago

Average price per month

Flight prices as travel date approaches

Is United Airlines cheaper than other airlines flying to Chicago?
With an average return price of $573, United Airlines is the most expensive airline flying into Chicago. The cheapest airline flying to Chicago is Allegiant Air.
Which other airlines fly to Chicago?
Along with United Airlines, you can also fly to Chicago with Southwest, American Airlines, Frontier, Contour, Denver Air Connection, Frontier, Delta, Southern / Mokulele, Allegiant Air and Allegiant Air.
How much is a flight to Chicago with United Airlines?
On average, United Airlines flights to Chicago cost $335 for one-way and $573 return.
Which airport do United Airlines flights to Chicago fly into?
United 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 Star Alliance that fly to Chicago?
Unfortunately, there are no other airlines in Star Alliance that fly to Chicago.

Looking to fly from the United States to Chicago with United Airlines? 25% of our users found flights for the following prices or less: From Ontario $158 one-way, $317 round-trip; from Allentown $308 one-way, $453 round-trip.
The cheapest flight to Chicago with United Airlines found on KAYAK in the last 2 weeks departed from Eau Claire and cost $92.

7.4

GoodBased on 8,696 verified guest reviews

7.3Comfort

7.7Boarding

7.1Entertainment

6.6Food

8.1Crew

Pros +

Cons -

Show reviews that mention

8.0 Very good

Anonymous, Apr 2025

Everything

10.0 Wonderful

David, Apr 2025

No issues, great flight, great crew

10.0 Wonderful

Vincenzo, Apr 2025

Friendly crew, all very smooth

8.0 Very good

Vincenzo, Apr 2025

Crew friendly and efficient. Nobody seated next to me

2.0 Poor

Brant, Apr 2025

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

10.0 Wonderful

Anonymous, Apr 2025

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

8.0 Very good

Anonymous, Apr 2025

A bit rush for transit. Food and entertainment are not available

8.0 Very good

Anonymous, Apr 2025

So far so good but food and entertainment are not available for this flight

10.0 Wonderful

Dr. Joseph, Apr 2025

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

8.0 Very good

Leslie, Apr 2025

Good

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Find cheap United Airlines flights to Chicago from $59

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Cheap United Airlines Flight Deals to Chicago

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Recent one-way United Airlines flight deals to Chicago

Recent last minute United Airlines flight deals to Chicago

Recent direct United Airlines flight deals to Chicago

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When to book flights with United Airlines to Chicago

FAQs for flying to Chicago with United Airlines

Is United Airlines cheaper than other airlines flying to Chicago?

Which other airlines fly to Chicago?

How much is a flight to Chicago with United Airlines?

Which airport do United Airlines flights to Chicago fly into?

Are there any other airlines in Star Alliance that fly to Chicago?

Top tips for your flights to Chicago with United Airlines

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