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$23 Find cheap flights from North America to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
sáb 8/24
sáb 8/31

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Good to know

Low season

January

High season

July

Cheapest flight

$23
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Boston to Chicago O'Hare Airport

FAQs for booking flights from North America to Chicago

  • How does KAYAK find such low prices on flights from North America to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from North America to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from North America to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from North America is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from North America to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to North America with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from North America to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from North America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from North America to Chicago?

Find which airlines fly direct from North America to Chicago, which days they fly and book direct flights.

Nonstop departures

North America to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

See more direct flights

Nonstop returns

Chicago to North America

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

See more direct flights
See more direct flights

Top 5 airlines serving from North America to Chicago

Need help choosing which airline to fly with from North America to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 9630 reviews
8.0Entertainment
7.4Food
7.9Comfort
8.2Boarding
8.6Crew
Airline reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

6.0 GoodKathy, Jul 2024ANC - SLC
Read more about Delta reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

We requested wheelchair assistance at ATL. This request was booked in advance of travel, we have requested this service before. We have had issues with accommodations for accessibility in the past, but this was beyond not having a chair on the ramp. We arrived in ATL international gates and had to search for a wheelchair for 40 mins. There were no delta or airport employees available to help. No service phones, nothing. With the help of another passenger I was able to get my elderly mother from the plane to the gate seating bench. She was able to wait there while I searched for a wheel chair.

Flights were terribly delayed. I was at At,anta Airport for over 4 hours waiting for my connection.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

Excellent. No issue and it was on time and arrived early, the best!

You cancelled my flight and made me Sleep at the airport.

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

The new Airbus A231neo has neat tech but the economy seats are so tight together that I always had my shoulders against one passenger or the other. I was very miffed that Basic Economy REQUIRES check-in of bags other than your personal carry-on; if you want to offer low-cost airline prices and then add services for a fee, just let me carry on my duffel. Hell, I could have put my carry on IN the duffel and called it a day but the gate agent would not let me; I ended up paying $40 for the risk of losing my bag. Not the worst flight, but far from the best.

My flight was delayed by a whole day, so I lost a day of my vacation.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

It was freezing in there. When I asked about it, the response is “we would have to tell them” and then she just walked away and continued to serve beverages. Everyone was cold and they didn’t care at all.

I did not enjoy continuously being lied to about the amount of time we would circle Chicago before deciding to redirect to Milwaukee. Then the amount of time we would sit on the ground in Milwaukee waiting for gas, or to take off again. Or the amount of time it would then take to get to Chicago again, or sit on the runway waiting for a gate. The whole time continuously hopefully we would make our connecting flight that kept getting delayed as well. Only to scramble and miss it. Enough with the BS. Tell me the truth. "Sorry, things are backed up and your probably not going to make your flight. You should rebook on the next flight now rather than wait." You'll never hear those words from an airline. Speaking of which. If the flight has been redirected and/or is seriously delayed, how about making the WiFi free for everyone so they get to rebooking and reserving hotel rooms while still in the air. You've inconvenienced me already and now you want me to pay $20 for Internet so I can try to make other plans. Absolutely disgusting!

Great flight. The captain did a great job of minimizing some minor turbulence and in general it was a smooth flight. Early departure and early arrival at destination. Great service.

Our flight left on time and we arrived a few minutes early. Great service!

Our 9:10 am scheduled flight continued to get delayed all day with no information given from the agents as to why. It wasn’t until I went to the customer service desk and got us switched to another flight at 2:44 pm (that wasn’t nonstop like our booked flight) that the agent finally was able to find out it was due to a fuel leak. I don’t know if our original flight ever took off but I don’t find it acceptable to leave people sitting in an airport all day with no explanation.

I am very disappointed with american. We have flown American airlines numerous times, as well as other airlines and never had such an experience. My son's flight for Sunday afternoon was cancelled around 11 am. We were told not to do anything bec AA would. After an hour of not seeing a change in his flight status. I called AA. I was on hold for half hour then opted for a call back. That call back never came. So I called again, in meantime I started looking online at my options. No flights were leaving that day from AA. But other airlines were flying out. We needed our son in Chicago asap.i kept calling AA for a callback, but never received one. Finally i called back later in the afternoon and a representative answered the call. She told me there were no flights out till Tuesday morning. I asked how this is possible, I had seen flights from AA and other airlines leaving Monday. She said she checked all NYC airports and there were no AA flights till Tuesday AM. Then I asked about getting on another airline. She responded i would be responsible for that. When I asked how AA would reimburse. She became nasty and told me AA has not responsibility to reimburse anything they will put me in a flight for Tuesday morning. When i explained he must be there Monday by 8am, she told me there's nothing to do and practically hung up. At that point I just asked her to book the Tuesday morning flight. I had this experience with other airlines, cancelled due to weather and they and their reps were much more helpful. Either way Tuesday morning flight was delayed as well. Over an hour! I expect more from AA.

The flight from Venice to Chicago was flawless. The flight crew was outstanding

When you pay for Premium Economy on an 787 and you’re promised amenities for the extra money, you expect them to work. They didn’t. USB connector wouldn’t charge continuously. 120v outlet wouldn’t hold anything you plugged into it. The adapter would just fall out. The noise canceling headphones stopped noise cancelling in the first 15 minutes for EVERYONE. No one on the plane knew how to fix it so I couldn’t listen to any movies. I just put in my AirPods and went to sleep. Very unhappy with the crappy Panasonic entertainment system. I won’t buy premium again.

Our flight was delayed by 18 hours. Poor accommodations made and no apology.

This flight was awful all around. Delays on the tarmac at PHL before takeoff and at the tarmac in Chicago caused me to miss my final connection. This was completely avoidable, in my opinion.

For the price we paid, the service was outstanding, we took off on time, everything went very smoothly, we landed on time, and we didn't need anything extra.

You get what you pay for, but those tickets weren't cheap, so I expected better, but Spirit is just one of those airlines.

Cancelled the return flight moments before boarding, horrible customer service in assisting with any rebooking. Never again will I fly Spirit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Better than expected.on time. Friendly staff in NY however MYR not so nice.

The flight crew and flight attendants are poorly trained and demonstrate poor professionalism. They have a sloppy appearance and communicate with patrons poorly. It is embarrassing for them to be representatives of an airline and for them to be called professionals.

After 5 hours of delay, they cancelled the flight. Very disappointed

My flight to LA was cancelled. I waited at the airport for 3 hrs saying it was delayed and then all of a sudden it was cancelled. Frontier only gave me a voucher and refund but could not rebook me. Flights on other airlines were too expensive last minute. I had to drive down to LA and didn’t even take my return flight home since I had to drive. One of the worst airline experiences in my life. It’s crazy how airlines can just upend people’s plans just like that.

Very delayed with little to no communication from the captain or flight crew. All announcements made were not audibly understood by passengers. Very poor communication. After arrival it took approximately 20 minutes to get a jet bridge to the plane.

Flying Frontiier was extremely poor!! I paid for a7:15am flight on flight 1601 from PHL To Las Vegas and the delay was brutally, excruciatingly and disgustingly long (8 hrs). I arrived by Uber to PHL at 5:30 am and had to spend the entire 8 hr delay inside the airport. Even more atrocious was that the flight was delayed twice. On the phone with customer service for two hours and was not fully compensated. I feel taken advantage of with this airline. They offered a menial couched for another flight within 90 days to me and my husband who has never flown but this experience has made us almost 100% sure to not fly this airline and will suggest that others don’t either. We don’t want to book ever again, don’t want a menial voucher and I believe by standard and because the flight was delayed for 8 hours, I should be fully reimbursed for the entire round trip. There is no excuse why this should have ever occurred. After sharing my experience with others in Vegas and Philadelphia, I was told that Frontier airlines is notorious for long delayed flights, poor customer service and refusal to compensate people correctly. I’m very nervous to see what departing from Vegas to Philadelphia will bring.

I fly Frontier often and generally don't have any issues. For some reason, the Denver to Houston's George Bush Intercontinental (IAH) flight always needs to wait on the tarmac in Houston because a gate is not available after landing. I've been stuck for as little as 15 minutes and as much as a little over an hour. I know only fly the Frontier Denver to IAH route when there is not an available flight to Houston Hobby (HOU).

Flight was 3 hours late leaving. Poor communication from the staff about delays. Impossible to get in touch with customer service (by design). And it actually didn't come out to be much cheaper than a non-budget airline! Not worth the headache, I'm never flying Frontier again

I’ve never flown frontier without a flight getting canceled. I understand that things go wrong with planes, but all other airlines handle cancellations so well. Frontier becomes a dumpster fire if a problem appears for them.

Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.

Book cheap flights from North America to Chicago

Recent round-trip flight deals

10/5sáb
nonstopSpirit Airlines
2h 52mBOS-ORD
10/8ter
nonstopSpirit Airlines
2h 25mORD-BOS
$40
9/7sáb
nonstopSpirit Airlines
2h 52mBOS-ORD
9/14sáb
nonstopSpirit Airlines
2h 25mORD-BOS
$47
8/19seg
nonstopFrontier
2h 37mDFW-ORD
8/20ter
nonstopFrontier
2h 29mORD-DFW
$56
9/10ter
nonstopFrontier
2h 24mDFW-ORD
9/11qua
nonstopFrontier
2h 22mORD-DFW
$57
9/5qui
nonstopDelta
2h 56mJFK-ORD
9/9seg
nonstopDelta
2h 26mORD-JFK
$108
9/14sáb
nonstopUnited Airlines
4h 22mSFO-ORD
9/17ter
nonstopUnited Airlines
4h 43mORD-SFO
$119
8/24sáb
nonstopAmerican Airlines
2h 14mBWI-ORD
8/26seg
nonstopAmerican Airlines
1h 55mORD-BWI
$119
8/14qua
nonstopDelta
2h 56mJFK-ORD
8/25dom
nonstopDelta
2h 16mORD-JFK
$134
9/13sex
nonstopAmerican Airlines
2h 15mBWI-ORD
9/16seg
nonstopAmerican Airlines
1h 52mORD-BWI
$139
8/13ter
nonstopUnited Airlines
2h 35mEWR-ORD
8/27ter
nonstopUnited Airlines
2h 14mORD-EWR
$159

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Recent one-way flight deals

9/28sáb
nonstopSpirit Airlines
2h 52mBOS-ORD
$23
9/18qua
nonstopSpirit Airlines
2h 52mBOS-ORD
$24
8/17sáb
nonstopFrontier
2h 49mDFW-ORD
$28
9/24ter
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2h 24mDFW-ORD
$29
9/6sex
nonstopUnited Airlines
2h 36mLGA-ORD
$64
10/5sáb
nonstopAmerican Airlines
2h 42mJFK-ORD
$68
10/29ter
nonstopDelta
2h 50mJFK-ORD
$69
8/31sáb
nonstopAmerican Airlines
2h 51mJFK-ORD
$70
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1 stopDelta
4h 43mEWR-ORD
$79
8/23sex
nonstopUnited Airlines
2h 10mDCA-ORD
$87

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Last minute flights from North America to Chicago

Last minute flight, train and bus deals

7/30ter
nonstopSpirit Airlines
2h 38mLGA-ORD
7/31qua
nonstopSpirit Airlines
2h 16mORD-LGA
$97
7/30ter
nonstopSpirit Airlines
2h 38mLGA-ORD
8/6ter
nonstopSpirit Airlines
2h 18mORD-LGA
$98
7/30ter
nonstopFrontier
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8/1qui
nonstopFrontier
2h 35mORD-DFW
$134
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nonstopFrontier
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8/7qua
multi-stopFrontier
4h 46mORD-DFW
$139
7/30ter
nonstopAmerican Airlines
2h 35mEWR-ORD
8/1qui
nonstopAmerican Airlines
2h 10mORD-EWR
$181
7/30ter
nonstopDelta
2h 58mLGA-ORD
8/1qui
nonstopDelta
2h 14mORD-LGA
$181
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nonstopAmerican Airlines
2h 35mEWR-ORD
8/2sex
nonstopAmerican Airlines
2h 04mORD-EWR
$194
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nonstopDelta
2h 58mLGA-ORD
8/2sex
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$194
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nonstopUnited Airlines
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8/2sex
nonstopUnited Airlines
2h 35mORD-BOS
$257
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2h 35mEWR-ORD
8/19seg
nonstopUnited Airlines
2h 29mORD-EWR
$302

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Flights to Chicago

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Chicago - North America

Cabin classes:

$257
$209
$213
$24