$52 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 5/8. 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, 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

Mon, May 18 - Wed, May 20
Frontier Logo
10:17 pm - 12:52 am
DFW
-
ORD
2h 35mnonstop
Frontier Logo
4:21 pm - 7:23 pm
ORD
-
DFW
3h 02mnonstop
$78Frontier
Mon, Apr 13 - Sat, Apr 18
Frontier Logo
8:48 pm - 11:23 pm
DFW
-
ORD
2h 35mnonstop
Frontier Logo
3:23 pm - 6:27 pm
ORD
-
DFW
3h 04mnonstop
$79Frontier
Wed, Apr 22 - Tue, Apr 28
Frontier Logo
11:30 am - 2:07 pm
DFW
-
ORD
2h 37mnonstop
Frontier Logo
5:57 pm - 8:57 pm
ORD
-
DFW
3h 00mnonstop
$80Frontier
Tue, Apr 14 - Tue, Apr 21
Spirit Airlines Logo
6:30 am - 8:01 am
LGA
-
ORD
2h 31mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$87Spirit Airlines
Tue, Apr 14 - Wed, Apr 15
Spirit Airlines Logo
6:30 am - 8:01 am
LGA
-
ORD
2h 31mnonstop
Spirit Airlines Logo
2:09 pm - 5:20 pm
ORD
-
LGA
2h 11mnonstop
$88Spirit Airlines
Sat, Apr 25 - Mon, Apr 27
American Airlines Logo
1:45 pm - 3:09 pm
DCA
-
ORD
2h 24mnonstop
American Airlines Logo
9:01 pm - 11:57 pm
ORD
-
DCA
1h 56mnonstop
$204American Airlines
Wed, Apr 1 - Wed, Apr 1
United Airlines Logo
7:30 am - 8:47 am
DCA
-
ORD
2h 17mnonstop
United Airlines Logo
2:00 pm - 5:04 pm
ORD
-
DCA
2h 04mnonstop
$209United Airlines
Sat, Apr 11 - Sat, Apr 11
American Airlines Logo
6:36 am - 10:11 am
DCA
-
ORD
4h 35m
1 stop
American Airlines Logo
9:01 pm - 11:57 pm
ORD
-
DCA
1h 56mnonstop
$210American Airlines
Sat, Apr 25 - Tue, Apr 28
Southwest Logo
6:00 am - 3:30 pm
DCA
-
ORD
10h 30m
1 stop
Southwest Logo
2:40 pm - 9:55 pm
ORD
-
DCA
6h 15m
1 stop
$212Southwest
Wed, Apr 15 - Sat, Apr 25
United Airlines Logo
12:45 am - 7:07 am
SFO
-
ORD
4h 22mnonstop
United Airlines Logo
9:40 pm - 12:39 am
ORD
-
SFO
4h 59mnonstop
$235United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$52
Best time to beat the crowds with an average 5% 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 
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 4317 reviews
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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.

Had to pay for my bag a mini weekender bag 100 dollar fee

The flight was delayed for unknown reasons while other airlines weren’t. It was very frustrating.

Everything was good. On time, boarding fast, flight attendants friendly.

Spirit has always and will always stink. Absolute worst airline around.

Not seat assigned because overbooking. We could go because some people decided to give their seats.

The flights were very uncomfortable the seats don't have much leg room at all and they are pretty hard as well.

Our outgoing flight was cancelled two hours before boarding and Spirit was not able to get us onto another flight. Their customer service was slow and unhelpful.

spirit delayed my first flight 9 hours and then cancelled my flight back home. Very disappointed with their service.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

Frontier line changes my flight schedule with out my authorization. They never ask me and with out my concern they cut off 4 hours of my vacation they force my to leave 4 hours early from Puerto Rico.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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.