$65 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 9/14. 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.
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Cheap Flights from North America to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from North America 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 flight deals from North America to Chicago

Wed, Sep 17 - Sun, Sep 21
Frontier Logo
8:00 am - 10:40 amDFW-ORD
2h 40mnonstop
Frontier Logo
6:00 am - 9:16 amORD-DFW
27h 16m1 stop
$114Frontier
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Wed, Oct 8 - Tue, Oct 14
Frontier Logo
8:00 am - 1:38 pmDFW-MDW
5h 38m1 stop
Frontier Logo
5:20 pm - 8:01 pmMDW-DFW
2h 41mnonstop
$114Frontier
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Tue, Dec 9 - Fri, Dec 12
Spirit Airlines Logo
7:20 am - 9:44 amDFW-ORD
2h 24mnonstop
Spirit Airlines Logo
3:11 pm - 5:42 pmORD-DFW
2h 31mnonstop
$121Spirit Airlines
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Mon, Dec 8 - Thu, Dec 11
Spirit Airlines Logo
6:47 pm - 9:15 pmDFW-ORD
2h 28mnonstop
Spirit Airlines Logo
3:11 pm - 5:42 pmORD-DFW
2h 31mnonstop
$128Spirit Airlines
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Wed, Sep 24 - Tue, Sep 30
American Airlines Logo
5:33 pm - 8:01 pmDFW-ORD
2h 28mnonstop
American Airlines Logo
4:12 pm - 6:45 pmORD-DFW
2h 33mnonstop
$157American Airlines
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Sat, Sep 13 - Wed, Sep 17
United Airlines Logo
9:18 am - 10:55 amLGA-ORD
2h 37mnonstop
United Airlines Logo
11:00 am - 2:19 pmORD-LGA
2h 19mnonstop
$157United Airlines
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Thu, Sep 4 - Sun, Sep 7
United Airlines Logo
10:20 am - 11:57 amLGA-ORD
2h 37mnonstop
United Airlines Logo
8:55 am - 12:14 pmORD-LGA
2h 19mnonstop
$162United Airlines
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Mon, Oct 27 - Tue, Oct 28
American Airlines Logo
7:40 pm - 9:24 pmEWR-ORD
2h 44mnonstop
American Airlines Logo
8:35 pm - 11:59 pmORD-EWR
2h 24mnonstop
$175American Airlines
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Sat, Aug 30 - Sat, Sep 6
Southwest Logo
10:30 am - 10:00 pmSEA-ORD
9h 30m1 stop
Southwest Logo
4:20 pm - 10:30 pmORD-SEA
8h 10m1 stop
$203Southwest
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Tue, Sep 16 - Tue, Sep 23
Southwest Logo
5:15 am - 2:10 pmSEA-ORD
6h 55m1 stop
Southwest Logo
7:30 am - 1:40 pmORD-SEA
8h 10m1 stop
$208Southwest
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Good to know

Low seasonJanuary
Cheapest flight$65
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Dallas/Fort Worth Airport to Chicago O'Hare Airport

Flights from North America to Chicago: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from North America to Chicago 
DouglasFlew with American AirlinesHSV-ORDJun 2025
Check your app for delay notices. This notice did come out early in the morning - I failed to check it. Checking it could have saved 4 hours at the airport
Verified travelerFlew with British AirwaysDSM-ORDJun 2025
Make sure your luggage receipts have the ID numbers on them
Verified travelerFlew with Air CanadaJAX-ORDApr 2025
Chicago is a huge airport, wear comfortable shoes if you're looking to make a connection. It might be a 15 minute speed walk. Jacksonville is a little more compact and easier to navigate. Lots of food and beverage options in each.
StaceyFlew with American AirlinesPHX-ORDFeb 2025
Don’t be that person who holds up the plane because of your carry on. Whether putting in over bin (able to lift it on your own) or refusing to not listen when space is full and need to check it.
Verified travelerFlew with United AirlinesBTV-ORDDec 2024
Get to know the airport plan in advance because it is a confusing one.
LisaFlew with United AirlinesYWG-ORDDec 2024
Turn on your data or the wifi in case gates change.
valerieFlew with Air CanadaSTL-ORDJan 2025
Usually it is unreliable - always leave lots of time for connection.
StephenFlew with United AirlinesEWR-ORDJan 2025
Don't bring a carry on roller bag. It won't fit. They will gate check it. It will take forever.
RodFlew with United AirlinesSAN-ORDSep 2024
Yes! Don’t reserve a flight with less than 1 1/2 hour connection time or you have a good possibility of missing your connection.
GeraldFlew with Alaska AirlinesSFO-ORDOct 2024
Book a flight as early in the day as possible to avoid incoming flight delays.
BrianFlew with Air CanadaYYZ-ORDOct 2024
Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.
AdamFlew with SouthwestDEN-ORDOct 2024
Arriving T5 at ORD on Southwest is often a LONG walk, with no moving walkways going out, to baggage claim / pickup.
DinaFlew with United AirlinesHSV-ORDNov 2024
Be prepared for delays and plan to check your luggage. Overhead bins are ⅓ the size of a typical bin.
KimFlew with American AirlinesSNA-ORDNov 2024
Bring extra foods and buy extra drinks bring your meds
LeoFlew with United AirlinesCLT-ORDJun 2024
Get precheck TSA if you’re flying in early morning. Get a seat on the right side of the plane if you want to see sunrise.
Verified travelerFlew with American AirlinesPHL-ORDJul 2024
Fly out the night before you have anything to do in Chicago so you don’t get delayed and miss out on plans
JenniferFlew with American AirlinesCLT-ORDJul 2024
Both the Charlotte and O'Hare airports are large and well organized. Wear you comfy walking shoes and enjoy the journey!
CameonFlew with FrontierSLC-ORDJul 2024
Fly Delta! Book directly through the airline, not a second booking party.
GailFlew with JetBlueBOS-ORDJul 2024
Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.
SheenaFlew with SouthwestLGA-MDWJun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
Verified travelerFlew with United AirlinesSEA-ORDJul 2024
Budget if you’re planning on shopping for meals or souvenirs at Sea-Tac, it’s not cheap.
Steven AnthonyFlew with United AirlinesYUL-ORDAug 2024
Don't take the 6am flight. Airport security and customs only open at 430am. So if you show up the recommended 3 hours before, you're waiting in line for nothing
Verified travelerFlew with WestJetYYC-ORDJun 2024
checkin luggage online as they jack up the price 100% at airport
ShirleyFlew with United AirlinesLAX-ORDMay 2024
Check-in using the United AirLines app to access your boarding pass. Arrive at least two hours early at LAX airport.
JorgeFlew with FrontierCUN-ORDMar 2024
From Chicago Ohare to city center take the train blue line all the way to there for just 5 dollars
MichelleFlew with United AirlinesMBS-ORDApr 2024
Bring water on board and charge your devices in advance.
EllenFlew with United AirlinesGSP-ORDMay 2024
Greenville airport is small, getting through security won't take too long (particularly if you have Precheck). Be prepared to walk for 10-15 minutes from your arrival gate in O'Hare to your next departure gate, if you have one. Sometimes those gates are really close together, but my experience is that they are typically farther apart and require a solid walk.
Verified travelerFlew with SouthwestLAS-ORDMay 2024
Leave plenty of time to get your bag in Chicago if you check one. Took 45 minutes to get my bag this time.
Verified travelerFlew with Alaska AirlinesSDF-ORDApr 2024
If flight gets delayed. Be sure to ask the airlines you traveled with, to rebook the next available flight immediately.
Verified travelerFlew with United AirlinesYUL-ORDApr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment
RickyFlew with Spirit AirlinesDFW-ORDMar 2024
Uber pickup is in terminal 2 doors 2D/2E not available in terminal 1
KariFlew with British AirwaysLSE-ORDMay 2024
Ask for assistance. Chicago is huge airport 🛫 and can get lost easy.
Verified travelerFlew with United AirlinesYYZ-ORDMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time
CindyFlew with SouthwestTPA-MDWMar 2024
Don’t check a bag. Chicago takes forever to get your baggage.
yvgeniFlew with United AirlinesEWR-ORDJan 2024
Check the weather before flying , and don’t rely on getting on time to your destination
BrianFlew with United AirlinesDEN-ORDJan 2024
Big airport. Make sure you have enough time between flights for rest, eating, etc…
MoFlew with SouthwestOKC-MDWFeb 2024
Eat before you go. No ggod food at Midway.

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.

Reviews of the 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
SouthwestOverall score based on 4246 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Everything was on time and the crew was very helpful. Would definitely use again

The incoming plane ✈️ was delayed 5 hours en route to Raleigh. My flight was delayed for 5 hours 😢. Finally boarded and then de boarded due to an AC problem. A very tough and long night.

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

The flight was delayed be over 3 hours. I tried to get a refund for Vivian Kirby and my session kept being stopped. I was NEVER able to finish the prosses...after 2 hours of attempting.

My experience with Spirit was good, but the experience with Kayak was not. Based on the Spirit agent Kayak added an additional charge after purchasing the tickets. When I buy the tickets I paid the total amount and I only pay once. This time they added an additional charge because based on Spirit they partially charge the tickets and I still needed to pay a second time. This is not good at all and Unprofessional

Spirit gets such a bad rap. I have never had a bad experience with them and the crew is always friendly and funny. This trip I had knee replacement surgery surgery 10 weeks ago. It is still a little rough to get get from point a to point b. And Spirit was on top of it. When there was a seat available the stewardess asked me if I wanted to move to an open seat so I could elevate my leg on the empty seat? 5 stars all around. They helped me on and helped me off the plane. I can’t say enough about the crew!!

We liked the woman who worked our gate and waited with us for our plane. We changed gates 3 times. Our flight was supposed to leave at 11:28am. We actually left after 5pm. It was not a good situation. This delay cost us a lot of money.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to North America

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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