$23 Find Cheap Flights from Chicago to North America

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to North America departing on 9/20. 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

KAYAK searches hundreds of travel sites at once for deals on flights to North America

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to North America

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New Yorknonstop$62
Los Angeles
Los Angelesnonstop$75
Orlando
Orlandononstop$58
Las Vegas
Las Vegasnonstop$75
Miami
Miaminonstop$78
San Francisco
San Francisco1 stop$153
Boston
Bostonnonstop$84
Washington, D.C.
Baltimorenonstop$73
Denver
Denvernonstop$66
Seattle
Seattle1 stop$152
Fort Lauderdale
Fort Lauderdalenonstop$84
Atlanta
Atlantanonstop$57
Dallas
Dallasnonstop$64
Phoenix
Phoenixnonstop$92
Tampa
Tampanonstop$73
Houston
Houstonnonstop$61
Cancún
Cancúnnonstop$198
Honolulu
Honolulu1 stop$413
San Diego
San Diegononstop$75
New York
New Yorknonstop$62
Los Angeles
Los Angelesnonstop$75
Orlando
Orlandononstop$58
Las Vegas
Las Vegasnonstop$75
Miami
Miaminonstop$78
San Francisco
San Francisco1 stop$153
Boston
Bostonnonstop$84
Washington, D.C.
Baltimorenonstop$73
Denver
Denvernonstop$66
Seattle
Seattle1 stop$152
Fort Lauderdale
Fort Lauderdalenonstop$84
Atlanta
Atlantanonstop$57
Dallas
Dallasnonstop$64
Phoenix
Phoenixnonstop$92
Tampa
Tampanonstop$73
Houston
Houstonnonstop$61
Cancún
Cancúnnonstop$198
Honolulu
Honolulu1 stop$413
San Diego
San Diegononstop$75

Book Cheap Chicago to North America Plane Tickets

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

Thu, Sep 18 - Sat, Sep 20
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
Frontier Logo
1:02 pm - 3:17 pmMCO-ORD
3h 15mnonstop
$58Frontier
Find Deal
Sun, Sep 28 - Sat, Oct 4
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
Frontier Logo
1:02 pm - 3:17 pmMCO-ORD
3h 15mnonstop
$60Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Spirit Airlines Logo
11:12 am - 2:17 pmORD-LGA
2h 05mnonstop
Spirit Airlines Logo
7:59 pm - 9:18 amLGA-ORD
14h 19m1 stop
$62Spirit Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Spirit Airlines Logo
4:35 pm - 7:41 pmORD-LGA
2h 06mnonstop
Spirit Airlines Logo
7:59 pm - 9:18 amLGA-ORD
14h 19m1 stop
$66Spirit Airlines
Find Deal
Wed, Sep 3 - Thu, Sep 4
United Airlines Logo
1:12 pm - 4:30 pmORD-EWR
2h 18mnonstop
United Airlines Logo
6:00 am - 7:38 amEWR-ORD
2h 38mnonstop
$137United Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 17
United Airlines Logo
10:35 am - 1:52 pmORD-EWR
2h 17mnonstop
United Airlines Logo
9:44 pm - 11:25 pmEWR-ORD
2h 41mnonstop
$142United Airlines
Find Deal
Tue, Sep 16 - Wed, Sep 17
American Airlines Logo
7:05 am - 10:19 amORD-EWR
2h 14mnonstop
American Airlines Logo
7:30 am - 9:10 amEWR-ORD
2h 40mnonstop
$159American Airlines
Find Deal
Thu, Sep 4 - Sat, Sep 6
American Airlines Logo
8:41 pm - 11:59 pmORD-EWR
2h 18mnonstop
American Airlines Logo
2:27 pm - 4:04 pmEWR-ORD
2h 37mnonstop
$162American Airlines
Find Deal
Sat, Oct 25 - Fri, Oct 31
Delta Logo
7:37 am - 10:15 amORD-SEA
4h 38mnonstop
Delta Logo
5:55 pm - 11:50 pmSEA-ORD
3h 55mnonstop
$184Delta
Find Deal
Sat, Sep 6 - Sat, Sep 13
Delta Logo
7:15 am - 9:45 amORD-SEA
4h 30mnonstop
Delta Logo
5:59 pm - 11:59 pmSEA-ORD
4h 00mnonstop
$191Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to North America flights

Get data-powered insights and trends into flights from Chicago to North America to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to North America flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to North America from Chicago found in the last 72 hours was to New York, at $64 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Orlando Airport (MCO), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $89.

Can I save money by flying with a layover from Chicago to North America?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $592, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to North America?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to North America, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to North America is January, when tickets cost $157 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $250 and $237 respectively.

What’s the cheapest day of the week to fly from Chicago to North America?

The average price of all round-trip flights from Chicago to North America clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to North America on a Friday and more expensive on a Sunday. On your return trip to Chicago, you should consider flying back on a Tuesday, and avoid Sundays for better deals.

How far in advance should I book a flight from Chicago to North America?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to North America, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to North America, you should book around 3 weeks before departure, which saves you about 43% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$23
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago O'Hare Airport to New York LaGuardia Airport

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

Insights shared by verified travelers who flew the route from Chicago to North America 
NikhilFlew with Air CanadaORD-YYZJul 2025
small flight, not much storage space as per the passengers. Try to get a booking which is Group 1 or 2 latest.
RogerFlew with Japan AirlinesORD-PITJun 2025
Make sure when you go from one airline to another that your bag is marked properly so they can get it on the right damn airplane. I did that and it still didn’t make it.
Verified travelerFlew with United AirlinesORD-LASMar 2025
If you can select your seats in advance please do
AndreaFlew with United AirlinesORD-ATLMay 2025
Ask for stewards to assist and provide amenities or you won’t get them.
Verified travelerFlew with American AirlinesORD-TPADec 2024
I recommend having movies and songs downloaded on your device.
Dr. JosephFlew with American AirlinesORD-DFWJan 2025
Be very vigilant about the weather both in Chicago and in Dallas. Adverse weather in either area can affect the trip.
JanieFlew with SWISSORD-PHXFeb 2025
I think you should prebook food or bring your own food.
valerieFlew with Air CanadaORD-YULJan 2025
“Meal” usually means more than a light snack. I thought what they served was an appetizer not the total meal. So I’d eat before or bring food.
Verified travelerFlew with Spirit AirlinesORD-LASSep 2024
Make sure you get your seats booked at time of booking or at the least when you check in and make sure you check in at the earliest to have preferred seating.
MikeFlew with American AirlinesORD-LAXSep 2024
Arrive early, grab a bottle of soda before getting on the plane and open it in the terminal. If you wait until flying the pressure will decarbonize the drink.
Verified travelerFlew with Alaska AirlinesORD-PDXSep 2024
Not many amenities at the terminal. I would suggest grabbing anything that catches your eye before you get all the way down. There weren't a lot of Alaska flights out of Chicago, and we were at the extreme end of the terminal.
Verified travelerFlew with Air CanadaORD-YOWNov 2024
Ottawa, as a small airport is easiest to navigate! Overhead baggage compartments seem to be smaller, and on every flight they seem to need travellers to volunteer to put carryons in checked luggage instead.
Verified travelerFlew with British AirwaysORD-CIDSep 2024
Easy hop but we sure went to the most remote o’hare gate I think, prepare to walk a mile!
Verified travelerFlew with Porter AirlinesMDW-YTZSep 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
mauriceFlew with IberiaORD-JFKSep 2024
You should arrive early, take a lighht snack and be prepared for delays.
HeatherFlew with LufthansaORD-MKEAug 2024
Make sure there's enough time between connections to go through customs and recheck your luggage. They will not let you proceed so you can't even try to run and catch the flight if you want to.
AlexanderFlew with Spirit AirlinesORD-LGAMay 2024
Know your connection options — specially when LaGuardia Airport (LGA) only has buses going to/from the airport to the rest of the city. Luckily, the one to the subway station (Q70) is free-of-charge to ride on!
Verified travelerFlew with United AirlinesORD-PHXApr 2024
Use the find my gate feature on the flights phone app if available as the airport is a bit confusing
AyannaFlew with Spirit AirlinesORD-TPAMay 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
PaulFlew with Alaska AirlinesORD-SEAApr 2024
The flight is long, at over four hours. I would try to get a window or aisle seat to be more comfortable. I would check with other airlines that allow you to choose your seat even if you are in the economy section. I would bring your own food on the plane as the service was sometimes sketchy.
EllenFlew with United AirlinesORD-DSMMay 2024
The flight is short enough that full beverage and snack service is limited or not offered at all. On this flight, we were offered orange juice or water. It makes sense that they can't do the full service, and doesn't bother me, but it's something to be aware of.
Verified travelerFlew with Alaska AirlinesORD-SEAApr 2024
If you miss your flight ask any alaska agent to how and where to rebook the flight.
UzomaFlew with American AirlinesORD-DCAJan 2024
ORD and DCA are nice airports with plenty of space. ORD is always busy so allow ample time to drive there, drop your bag, and go through security if you don't have TSA pre check.
LaurenFlew with Spirit AirlinesORD-MCOFeb 2024
If you can get by with a personal item, spirit has the best prices often at the best times to fly chicago to orlando for a weekend
Dr. JosephFlew with American AirlinesORD-CLTJan 2024
Be prepared to walk long distances in Charlotte. Make sure your layover time is sufficient to transition between arrival and departure gates.
Verified travelerFlew with United AirlinesORD-YOWJan 2024
I always expect issues with United but there doesn't seem to be another airline to use. Advice: Give yourself and extra day to get anywhere - don't be in a hurry to get home either.

FAQs - booking North America flights

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

    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 Chicago to North America.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to 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 Chicago to North America?

    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 from Chicago to North America with an airline and back with another airline.

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

    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 from Chicago to North America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to North America?

    The cheapest time of day to fly to North America is generally at night, when round-trip flights cost $237 on average. Morning departures are around 9% cheaper than evening flights, on average. The most expensive time of day to fly to North America is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $391.

Top tips for finding cheap flights to North America

  • Looking for a cheap flight? 25% of our users found tickets from Chicago to the following destinations at these prices or less: Miami $137 one-way - $112 round-trip

Reviews of the top 5 airlines serving from Chicago to North America

 
Need help choosing which airline to fly with from Chicago to North America? 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 4244 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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

4.0 OkayDavid, Aug 2025DTW - STL
Read more Southwest reviews

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.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

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

I liked the check in procedure. The luggage charges and overweight cost can be better.

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.

Again, when I use Kayak I expect to pay the total amount and that´s it. Someone added an additional charge few days later after purchasing the tickets.

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

For the minimalist experience, it is really a great ride-- feels a little like public transport i guess

I didn’t mind being delayed due to weather, but continuing to post (and not update) that we would be delayed until after the flight was already supposed to have taken off was a bit much. In the future, please announce the delay even if the time is still unknown.

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.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

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

Everything you need to know for your flight to North America

Cabin class types available on flights to Chicago

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.