$53 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 5/27. 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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1 adult, Economy, 0 bags

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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

Tue, May 19 - Tue, Jun 9
Multiple Airlines Logo
12:38 pm - 3:03 pm
DFW
-
ORD
2h 25mnonstop
Multiple Airlines Logo
9:22 am - 12:09 pm
ORD
-
DFW
2h 47mnonstop
$113Multiple Airlines
Tue, May 12 - Wed, May 13
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$113Frontier
Sat, Aug 15 - Tue, Aug 18
Frontier Logo
1:25 pm - 4:08 pm
DFW
-
ORD
2h 43mnonstop
Frontier Logo
9:34 pm - 12:19 am
ORD
-
DFW
2h 45mnonstop
$114Frontier
Tue, May 19 - Tue, May 26
Spirit Airlines Logo
12:38 pm - 3:03 pm
DFW
-
ORD
2h 25mnonstop
Spirit Airlines Logo
8:00 am - 10:32 am
ORD
-
DFW
2h 32mnonstop
$117Spirit Airlines
Wed, Jun 17 - Mon, Jun 22
Spirit Airlines Logo
8:42 pm - 10:20 pm
LGA
-
ORD
2h 38mnonstop
Spirit Airlines Logo
1:57 pm - 5:14 pm
ORD
-
LGA
2h 17mnonstop
$143Spirit Airlines
Wed, Jun 24 - Sun, Jul 5
Delta Logo
3:00 pm - 5:11 pm
JFK
-
ORD
3h 11mnonstop
Delta Logo
6:05 am - 9:26 am
ORD
-
JFK
2h 21mnonstop
$177Delta
Sat, May 23 - Tue, May 26
United Airlines Logo
7:11 pm - 8:35 pm
BWI
-
ORD
2h 24mnonstop
United Airlines Logo
9:25 pm - 12:33 am
ORD
-
BWI
2h 08mnonstop
$212United Airlines
Wed, May 27 - Sat, May 30
Delta Logo
3:08 pm - 9:53 pm
IAD
-
ORD
7h 45m
1 stop
Delta Logo
5:41 pm - 11:39 pm
ORD
-
IAD
4h 58m
1 stop
$228Delta
Sat, Jul 25 - Sat, Aug 1
American Airlines Logo
11:16 pm - 5:40 am
SFO
-
ORD
4h 24mnonstop
American Airlines Logo
6:45 am - 9:26 am
ORD
-
SFO
4h 41mnonstop
$273American Airlines
Wed, May 27 - Wed, Jun 3
American Airlines Logo
2:42 pm - 9:34 pm
SFO
-
ORD
4h 52mnonstop
American Airlines Logo
6:45 am - 9:25 am
ORD
-
SFO
4h 40mnonstop
$282American Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$53
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 1% 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 
DeepaFlew with American Airlines
DFW
-
ORD
Apr 2026
The TSA precheck feature is useful, and the security checkpoint to gate walk is around 20 mins, not too bad.
CupcakeFlew with Alaska Airlines
SAN
-
ORD
Apr 2026
Please bring a water bottle for hydration during the flight.
Verified travelerFlew with American Airlines
GSP
-
ORD
Apr 2026
Chicago has a enormous airport so be ready to walk and transfer to international flights by train via terminal
Dr. JosephFlew with United Airlines
ATL
-
ORD
Apr 2026
Always keep track of the weather at both locations and where the inbound flight is coming from.
EricFlew with American Airlines
OMA
-
ORD
Apr 2026
The connections in Chicago can be tricky. Make sure you have enough time to make your connection.
Verified travelerFlew with United Airlines
ATL
-
ORD
Apr 2026
Make sure the flight you select has more than 3 hours as time allotted for transiting to another flight. Most of United Airlines flights get delayed and if you don’t have enough time, you’ll be missing the next flight for sure. Have extra budget for shelter expenses because most of the economy tickets does not qualify for shelter accommodation/ voucher when your flight is delayed.
YesicaFlew with United Airlines
CHS
-
ORD
Feb 2026
Utilize the mobile app of your airline it will give you all the updates and information you need
BillFlew with Frontier
MCO
-
ORD
Dec 2025
Wear comfortable clothing and make sure you layer. We went from 80o to 30o,
MMFlew with United Airlines
YVR
-
ORD
Jan 2026
Pay extra for Boarding Zone 2 to make sure your carry on, gets on the plane.
Thrinadh KumarFlew with United Airlines
OGG
-
ORD
Dec 2025
Flight is conjusted. Difficult to sleep. Carry pillows and sleep well beforeyou travel
StephenFlew with United Airlines
SMF
-
ORD
Jan 2026
If you're trying to make a connecting flight make sure you allow PLENTY of time between flights or be prepared to miss the next flight. Make sure to use the restroom at the last possible moment before landing because you could be sitting on the taxiway for 5 more minutes... 5 more minutes... 5 more minutes... until it's been nearly 2 hours. Don't trust the airline provided ETA provided by apps they don't update it until long after you're delayed. If someone is showing up to give you a ride, make sure they have hours to wait for you.
JeremyFlew with United Airlines
XNA
-
ORD
Nov 2025
Beware short connection times on flights connecting in Chicago.
DouglasFlew with American Airlines
HSV
-
ORD
Jun 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 Airways
DSM
-
ORD
Jun 2025
Make sure your luggage receipts have the ID numbers on them
Verified travelerFlew with Air Canada
JAX
-
ORD
Apr 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 Airlines
PHX
-
ORD
Feb 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 Airlines
BTV
-
ORD
Dec 2024
Get to know the airport plan in advance because it is a confusing one.
LisaFlew with United Airlines
YWG
-
ORD
Dec 2024
Turn on your data or the wifi in case gates change.
valerieFlew with Air Canada
STL
-
ORD
Jan 2025
Usually it is unreliable - always leave lots of time for connection.
StephenFlew with United Airlines
EWR
-
ORD
Jan 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 Airlines
SAN
-
ORD
Sep 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.
FrancisFlew with United Airlines
LAX
-
ORD
Sep 2024
Check the weather, or bring a. Raincoat! Being from sunny California, I forget it isn’t always sunshine in other states!
GeraldFlew with Alaska Airlines
SFO
-
ORD
Oct 2024
Book a flight as early in the day as possible to avoid incoming flight delays.
BrianFlew with Air Canada
YYZ
-
ORD
Oct 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 Southwest
DEN
-
ORD
Oct 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 Airlines
HSV
-
ORD
Nov 2024
Be prepared for delays and plan to check your luggage. Overhead bins are ⅓ the size of a typical bin.
KimFlew with American Airlines
SNA
-
ORD
Nov 2024
Bring extra foods and buy extra drinks bring your meds
LeoFlew with United Airlines
CLT
-
ORD
Jun 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 Airlines
PHL
-
ORD
Jul 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 Airlines
CLT
-
ORD
Jul 2024
Both the Charlotte and O'Hare airports are large and well organized. Wear you comfy walking shoes and enjoy the journey!
CameonFlew with Frontier
SLC
-
ORD
Jul 2024
Fly Delta! Book directly through the airline, not a second booking party.
GailFlew with JetBlue
BOS
-
ORD
Jul 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 Southwest
LGA
-
MDW
Jun 2024
Get to the airport early. NY airports are always busy, even when you have TSA pre check
Verified travelerFlew with United Airlines
SEA
-
ORD
Jul 2024
Budget if you’re planning on shopping for meals or souvenirs at Sea-Tac, it’s not cheap.
Steven AnthonyFlew with United Airlines
YUL
-
ORD
Aug 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 WestJet
YYC
-
ORD
Jun 2024
checkin luggage online as they jack up the price 100% at airport
ShirleyFlew with United Airlines
LAX
-
ORD
May 2024
Check-in using the United AirLines app to access your boarding pass. Arrive at least two hours early at LAX airport.
JorgeFlew with Frontier
CUN
-
ORD
Mar 2024
From Chicago Ohare to city center take the train blue line all the way to there for just 5 dollars
MichelleFlew with United Airlines
MBS
-
ORD
Apr 2024
Bring water on board and charge your devices in advance.
EllenFlew with United Airlines
GSP
-
ORD
May 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 Southwest
LAS
-
ORD
May 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 Airlines
SDF
-
ORD
Apr 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 Airlines
YUL
-
ORD
Apr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment
RickyFlew with Spirit Airlines
DFW
-
ORD
Mar 2024
Uber pickup is in terminal 2 doors 2D/2E not available in terminal 1
KariFlew with British Airways
LSE
-
ORD
May 2024
Ask for assistance. Chicago is huge airport 🛫 and can get lost easy.
Verified travelerFlew with United Airlines
YYZ
-
ORD
Mar 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 Southwest
TPA
-
MDW
Mar 2024
Don’t check a bag. Chicago takes forever to get your baggage.
yvgeniFlew with United Airlines
EWR
-
ORD
Jan 2024
Check the weather before flying , and don’t rely on getting on time to your destination
BrianFlew with United Airlines
DEN
-
ORD
Jan 2024
Big airport. Make sure you have enough time between flights for rest, eating, etc…
MoFlew with Southwest
OKC
-
MDW
Feb 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 4314 reviews
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

Delayed both in takeoff and landing, trash plane no amenities, I've said it before but I'll never fly Spirit again.

It’s was a cheap flight and they got us there safely. It’s just their whole business model that make the experience “meh.” They make you paranoid about whether your personal item is too big. They make you paranoid about being crammed into a middle seat at the back of the plane. They purposely cram people together leaving multiple rows completely empty and even after the door closes the FA’s announce that everyone has to sit in their assigned seat. We knew what we were buying and in that regard we got a cheap and safe flight but it felt like they do their best to take any enjoyment out of the experience. That’s all on management, not the crew.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
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Munster
Porter
Monticello
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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.