$66 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 10/17. 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
1 adult, Economy

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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

Mon, Sep 22 - Thu, Sep 25
Frontier Logo
9:59 pm - 11:20 pmBWI-ORD
2h 21mnonstop
Frontier Logo
6:11 pm - 9:14 pmORD-BWI
2h 03mnonstop
$108Frontier
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Sun, Nov 2 - Tue, Nov 11
 Logo
5:20 am - 7:54 amDFW-ORD
2h 34mnonstop
 Logo
10:05 pm - 12:34 amORD-DFW
2h 29mnonstop
Wed, Oct 1 - Wed, Oct 8
Spirit Airlines Logo
9:57 am - 9:58 pmDFW-ORD
12h 01m1 stop
Spirit Airlines Logo
7:43 pm - 9:45 amORD-DFW
14h 02m1 stop
$113Spirit Airlines
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Sun, Nov 9 - Mon, Dec 8
Spirit Airlines Logo
5:44 pm - 7:01 pmBWI-ORD
2h 17mnonstop
Spirit Airlines Logo
2:47 pm - 9:22 pmORD-BWI
5h 35m1 stop
$115Spirit Airlines
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Wed, Oct 1 - Wed, Oct 29
United Airlines Logo
5:20 pm - 6:35 pmBWI-ORD
2h 15mnonstop
United Airlines Logo
2:20 pm - 5:14 pmORD-BWI
1h 54mnonstop
$117United Airlines
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Sat, Oct 25 - Sat, Nov 1
American Airlines Logo
6:00 am - 7:16 amBWI-ORD
2h 16mnonstop
American Airlines Logo
8:20 am - 11:20 amORD-BWI
2h 00mnonstop
$118American Airlines
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Wed, Oct 8 - Fri, Oct 10
United Airlines Logo
12:35 pm - 2:25 pmBOS-ORD
2h 50mnonstop
United Airlines Logo
4:00 pm - 7:31 pmORD-BOS
2h 31mnonstop
$125United Airlines
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Tue, Oct 7 - Sun, Oct 12
American Airlines Logo
6:57 am - 8:55 amBOS-ORD
2h 58mnonstop
American Airlines Logo
7:00 am - 10:21 amORD-BOS
2h 21mnonstop
$129American Airlines
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Wed, Oct 29 - Wed, Nov 5
Southwest Logo
6:45 am - 2:00 pmBOS-ORD
8h 15m1 stop
Southwest Logo
1:45 pm - 10:15 pmORD-BOS
7h 30m1 stop
$130Southwest
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Wed, Dec 10 - Wed, Dec 17
Southwest Logo
6:05 am - 12:15 pmDCA-ORD
7h 10m1 stop
Southwest Logo
1:45 pm - 10:40 pmORD-DCA
7h 55m1 stop
$142Southwest
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Everything you should know

Cheapest round-trip
$108
Overall average: $257
Frontier
Mon 9/22Thu 9/25
BWI - ORD • Non-stop
Cheapest one-way
$66
Typical prices: $68-161
Frontier
Fri 10/17
DFW - ORD • Non-stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$66
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 2% increase in price.
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 4248 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
8.6Crew
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

Was good. I miss the free 2 checked bags. That was part of what made Southwest special

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

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 about 1 1/2 hours in Chicago, but other then that it was a good flight.

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 flight was on time and crew were nice, seats were tight and there was entertainment available

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..

Everything was fine. I'm average height and I pack light. I'm ready for my Spirit flight.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

Cancelled my flight last minute and did not help me rebook. It was a horrible experience.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

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.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

As expected. Nothing jumps out at me as bad or wrong, but the flight was fine. No complaints with pilot or crew. The flight left on time and arrived earlier than stated. Overall, I will continue to plan on flying with Spirit.

Horrible considering I didn’t go and I bought travel insurance and I didn’t receive a refund.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

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.

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to North America

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