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Find cheap United Airlines flights to Chicago from $59

1 adult
0 bags
Thu 6/13
Thu 6/20

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Good to know

Low season

January

High season

June

Cheapest flight

$59

Average price round-trip

$2,987

Good deal round-trip

$1,075

Good deal one-way

$259
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from New York LaGuardia Airport to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less
or less

When to book flights with United Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with United Airlines

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

    With an average return price of $567, United Airlines is cheaper than American Airlines when it comes to flights to Chicago. However, the cheapest airline flying to Chicago is Allegiant Air, with an average return price of $105.

  • Which other airlines fly to Chicago?

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

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

    On average, United Airlines flights to Chicago cost $363 for one-way and $567 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.

See more FAQs

Top tips for your flights to Chicago with United Airlines

  • 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 Washington, D.C. Dulles Intl Airport $142 one-way, $289 round-trip; from San Jose $210 one-way, $456 round-trip; from Fresno $236 one-way, $433 round-trip.
  • The cheapest flight to Chicago with United Airlines found on KAYAK in the last 2 weeks departed from Johnstown and cost $100.

United Airlines customer reviews

7.4
GoodBased on 10,980 verified guest reviews
7.7Boarding
6.7Food
7.2Comfort
7.1Entertainment
8.1Crew
Pros +
Cons -
Traveler rating:
Sort by:
R
6.8 Okay
Pros:The crew was excellent - courteous/aware/friendly. The flight, although 2 hours delayed (9;20pm scheduled departure) was pleasant and smooth. Also, the de-boarding process was surprisingly quick.
Cons:A 2 hour delay at 9:20pm at night is unfortunate yet frustrating experience, especially when we moved our flight up due to a travel warning for EWR (ironically enough, our originally scheduled flight (1922 MCO-EWR). I'm giving an overall OK (instead of good) due to the fact that there were no snacks (although I did not want anything, it didn't go unnoticed) and although there was free inflight entertainment for personal devices, I feel the passengers should have been given free internet access - in my opinion, it would have been the appropriate thing to do. In any case, this experience doesn't change my positive opinion of United.
A
4.6 Mediocre
Cons:The first contact in the airport was quite rude when informing me that I had to measure my suitcase for size. I have carried this suitcase on on every airline for over 10 years....the size got smaller and United got $25.00....not happy. There was NO free movies, no access to TV, flight pattern....nothing and it could not be turned off. ONE cookie for a coast-to-coast flight. What happened to United?
A
10.0 Wonderful
On time departure and arrival.
A
10.0 Wonderful
Pros:Nice smooth flight
Cons:Everything
B
5.6 Fair
Cons:More water, drinks. The food was absolutely horrible.
A
7.3 Good
Pros:Amazing crew
Cons:Tight seats, no access to actual WiFi unless you purchase a yearly or monthly plan
S
4.6 Mediocre
Pros:Ordered the Protein Box, it was ok.. crew members nice.
Cons:The Smell on the flight was unacceptable, I was sitting about a couple rows across the middle bathroom, and it smelled horrible, I had never had an experience like this on any other flight, I fly United many times a year, and this had me really uncomfortable for almost 5 hours, since the flight was delayed almost 1.5 hours while we sat onboard the aircraft at the gate, that had me miss dinner plans too in San Francisco as well. I really hope they can fix that, For the good of the passengers, felt like I was going to be nauseous all the time, and I'm really not someone that complains or takes time to review badly.
N
4.6 Mediocre
Cons:2.5 hour delay. No working bathrooms. Couldn't hear the tv and headphones that they gave out were useless.
A
2.0 Poor
Cons:Purchased tickets 4 months before this flight for a departure time of 6:05pm. Tried to check in and check baggage at 9:30am but was turned away saying I could only check in 3 hrs prior to my flight. Came back at 3:00pm to check-in and they could not find my information. An hour later they find out that they cancelled the flight and moved my departure time to 8:25am for that day. They say they emailed 3 times in May but I never got it (I'm a bit crazy about my email staying clean) so they say it might have went in to my spam folder due to they types of emails they send to customers. They only kept repeating that they notified me so there is nothing they could do. I ended up going to Air Canada to get a flight to PHX the next day. No apology, no help, no hotel for the night...Terrible experience by United. They gave me a customer relations group contact information to follow up with for complaint but since they sent me the 3 emails in May about the change, they have no liability to fix the situation.
A
2.0 Poor
Cons:Departure was delayed. No explanation. The boarding area is crowded and confusing. The plane's bins were too small for roller boards so passengers had to carry bags outdoors in snow and terrible wind, to get them loaded. The Newark airport where the plane landed was miserable! Departure from Newark was worse than landing if that could be possible! Awful!
Read more about United Airlines

Book Cheap flights with United Airlines to Chicago

Recent round-trip flight deals

5/27Mon
nonstopUnited Airlines
2h 35mLGA-ORD
5/31Fri
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$117
6/12Wed
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$127
6/8Sat
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Recent one-way flight deals

5/27Mon
nonstopUnited Airlines
2h 35mLGA-ORD
$59
6/26Wed
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2h 38mLGA-ORD
$64
6/4Tue
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2h 35mEWR-ORD
$69
5/30Thu
nonstopUnited Airlines
2h 50mBOS-ORD
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6/12Wed
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3h 58mSEA-ORD
$75
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8/17Sat
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2h 35mEWR-ORD
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8/21Wed
1 stopUnited Airlines
9h 45mSEA-ORD
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2h 35mLGA-ORD
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7/8Mon
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2h 46mBOS-ORD
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1 stopUnited Airlines
5h 05mDFW-ORD
$98

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Flights to Chicago - United Airlines

Return flight deals:

Chicago - United States

Cabin classes:

$326
First Class flights to Chicago
$296
Business Class flights to Chicago
$246
$37

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