CHI

Find cheap United Airlines flights to Chicago from $64

1 adult
1 adult, Economy

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

Recent round-trip United Airlines flight deals to Chicago

Sat, Nov 15 - Thu, Nov 20
United Airlines Logo
6:23 pm - 8:23 pmBOS-ORD
3h 00mnonstop
United Airlines Logo
6:15 am - 9:30 amORD-BOS
2h 15mnonstop
$127United Airlines
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Thu, Oct 16 - Mon, Oct 20
United Airlines Logo
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
United Airlines Logo
9:20 pm - 12:50 amORD-BOS
2h 30mnonstop
$133United Airlines
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Tue, Jan 6 - Tue, Jan 6
United Airlines Logo
8:15 am - 10:11 amLGA-ORD
2h 56mnonstop
United Airlines Logo
12:10 pm - 3:23 pmORD-LGA
2h 13mnonstop
$134United Airlines
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Wed, Nov 5 - Fri, Nov 7
United Airlines Logo
6:00 am - 8:00 amBOS-ORD
3h 00mnonstop
United Airlines Logo
9:25 pm - 12:45 amORD-BOS
2h 20mnonstop
$134United Airlines
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Sat, Nov 1 - Mon, Nov 3
United Airlines Logo
6:26 pm - 8:25 pmBOS-ORD
2h 59mnonstop
United Airlines Logo
6:15 am - 9:30 amORD-BOS
2h 15mnonstop
$135United Airlines
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Wed, Oct 22 - Wed, Oct 22
United Airlines Logo
7:28 am - 9:05 amLGA-ORD
2h 37mnonstop
United Airlines Logo
6:30 pm - 9:54 pmORD-LGA
2h 24mnonstop
$137United Airlines
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Thu, Nov 13 - Sun, Nov 16
United Airlines Logo
12:25 pm - 2:25 pmBOS-ORD
3h 00mnonstop
United Airlines Logo
9:25 pm - 12:45 amORD-BOS
2h 20mnonstop
$137United Airlines
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Thu, Oct 16 - Fri, Oct 17
United Airlines Logo
7:28 am - 9:05 amLGA-ORD
2h 37mnonstop
United Airlines Logo
5:00 pm - 8:17 pmORD-LGA
2h 17mnonstop
$138United Airlines
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Tue, Oct 14 - Wed, Oct 15
United Airlines Logo
8:25 am - 10:02 amLGA-ORD
2h 37mnonstop
United Airlines Logo
11:00 am - 2:19 pmORD-LGA
2h 19mnonstop
$139United Airlines
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Thu, Oct 16 - Sun, Oct 19
United Airlines Logo
6:00 am - 7:56 amBOS-ORD
2h 56mnonstop
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
$145United Airlines
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Good to know

Low seasonJanuary
Cheapest flight$64
Average price round-trip$449
Good deal round-trip$340
Good deal one-way$326
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Boston 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 $441, United Airlines is cheaper than Alaska Airlines when it comes to flights to Chicago. However, the cheapest airline flying to Chicago is Allegiant Air, with an average return price of $161.

  • Which other airlines fly to Chicago?

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

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

    On average, United Airlines flights to Chicago cost $323 for one-way and $441 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.

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 $184 one-way, $296 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.

United Airlines customer reviews

7.4
Good8,933 verified ratings
7.7Boarding
7.1Entertainment
7.3Comfort
6.6Food
8.1Crew
Pros +
  • The flight arrived early and that was great (in 143 reviews)
Cons -
  • Customer service was very poor. (in 236 reviews)
Show reviews that mention
Traveler rating:
Sort by:
D
8.0 Very good
It went easy and on time
J
10.0 Wonderful
N/A
A
6.0 Okay
Lufthansa was great from Lisbon to Frankfurt. The United Airlines flight from Frankfurt to Denver was very cramped. In that tight space, when the seat in front was fully declined I could barely move. I'm a fairly small person, I can't imagine what a larger person would feel like.
A
6.0 Okay
It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.
A
2.0 Poor
See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.
A
6.0 Okay
My husband and I had boarded the flight from Denver to Chicago, and one of the last passengers to get on the plane opened the overhead bin above my husband's seat and threw his bag out of the bin to make space for his own. He said, "Mine is bigger!" The flight attendant supported the new passenger. They didn't care that my husband has two artificial knees and must have the foot room in front of his seat to be able to fit his legs in -- and to be able to stand, much less walk, at the end of the flight. I have never seen this happen before, and it was a disaster.
A
2.0 Poor
Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.
T
10.0 Wonderful
You are working very good! Thanks.
A
6.0 Okay
Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours
A
2.0 Poor
I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

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.

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