$93 Find Cheap Flights from Chicago to North America - Compare and Save

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 8/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Chicago to North America

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New York2 stops$185
Orlando
Orlandononstop$182
Los Angeles
Los Angeles1 stop$200
Las Vegas
Las Vegas1 stop$214
San Francisco
San Franciscononstop$293
Miami
Miami1 stop$221
Boston
Boston1 stop$167
Fort Lauderdale
Fort Lauderdalenonstop$122
Denver
Denvernonstop$169
Seattle
Seattle1 stop$324
Atlanta
Atlantanonstop$146
Dallas
Dallas1 stop$206
Phoenix
Phoenix1 stop$253
Tampa
Tampa1 stop$207
Houston
Houston1 stop$170
Cancún
Cancún1 stop$312
San Diego
San Diego1 stop$303
Honolulu
Honolulu2 stops$647
New York
New York2 stops$185
Orlando
Orlandononstop$182
Los Angeles
Los Angeles1 stop$200
Las Vegas
Las Vegas1 stop$214
San Francisco
San Franciscononstop$293
Miami
Miami1 stop$221
Boston
Boston1 stop$167
Fort Lauderdale
Fort Lauderdalenonstop$122
Denver
Denvernonstop$169
Seattle
Seattle1 stop$324
Atlanta
Atlantanonstop$146
Dallas
Dallas1 stop$206
Phoenix
Phoenix1 stop$253
Tampa
Tampa1 stop$207
Houston
Houston1 stop$170
Cancún
Cancún1 stop$312
San Diego
San Diego1 stop$303
Honolulu
Honolulu2 stops$647

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

Wed, Aug 5 - Wed, Aug 12
Frontier Logo
5:13 pm - 9:25 pm
ORD
-
MCO
3h 12mnonstop
Frontier Logo
8:59 pm - 11:10 pm
MCO
-
ORD
3h 11mnonstop
$182Frontier
Tue, Aug 4 - Wed, Aug 5
Frontier Logo
1:50 pm - 10:15 pm
ORD
-
MCO
7h 25m
1 stop
Frontier Logo
1:45 pm - 7:53 pm
MCO
-
ORD
7h 08m
1 stop
$183Frontier
Thu, Jul 30 - Tue, Aug 11
American Airlines Logo
6:00 am - 9:17 am
ORD
-
LGA
2h 17mnonstop
American Airlines Logo
6:10 am - 7:59 am
LGA
-
ORD
2h 49mnonstop
$186American Airlines
Wed, Jul 29 - Sat, Aug 1
United Airlines Logo
10:03 am - 1:26 pm
ORD
-
LGA
2h 23mnonstop
United Airlines Logo
7:25 pm - 9:12 pm
LGA
-
ORD
2h 47mnonstop
$187United Airlines
Fri, Oct 9 - Sat, Oct 17
United Airlines Logo
7:45 pm - 11:10 pm
ORD
-
LGA
2h 25mnonstop
United Airlines Logo
8:27 pm - 10:11 pm
LGA
-
ORD
2h 44mnonstop
$188United Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
3:10 pm - 7:02 pm
ORD
-
MCO
2h 52mnonstop
American Airlines Logo
8:52 am - 11:00 am
MCO
-
ORD
3h 08mnonstop
$190American Airlines
Thu, Nov 5 - Thu, Jan 7
Delta Logo
6:00 am - 9:20 am
ORD
-
JFK
2h 20mnonstop
Delta Logo
8:10 am - 10:04 am
JFK
-
ORD
2h 54mnonstop
$192Delta
Thu, Aug 20 - Wed, Aug 26
Delta Logo
7:44 pm - 11:46 pm
ORD
-
LAX
6h 02m
1 stop
Delta Logo
5:46 pm - 11:48 pm
LAX
-
ORD
4h 02mnonstop
$200Delta
Wed, Aug 19 - Sun, Aug 23
Volaris Logo
1:59 am - 10:31 am
ORD
-
CUN
8h 32m
1 stop
Volaris Logo
9:50 pm - 5:52 am
CUN
-
ORD
8h 02m
1 stop
$312Volaris
Tue, Aug 25 - Sat, Aug 29
Volaris Logo
1:40 am - 10:03 am
ORD
-
CUN
8h 23m
1 stop
Volaris Logo
9:50 pm - 5:52 am
CUN
-
ORD
8h 02m
1 stop
$313Volaris
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 5 days was to Boston, at $149 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Mexico City (MEX), and the cheapest round-trip airline ticket found on this route in the last 5 days was $157.

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

The average price for all round-trip flights from Chicago to North America depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to North America is generally at night, when round-trip flights cost $277 on average. Morning departures are around 24% cheaper than evening flights, on average. The most expensive time of day to fly to North America is generally in the evening, which is peak travel time and where the average cost of a ticket is $374.

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 $415, 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 October, when tickets cost $276 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $381 and $359 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 Saturday, 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 2 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$93
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Chicago O'Hare Airport to Orlando 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 
ScottFlew with Air Canada
ORD
-
YUL
Jun 2026
Make sure you have enough time between connecting flights so ½ of your baggage doesn't miss the flight and take another 24hrs to show up
MarkFlew with American Airlines
ORD
-
LAX
Jun 2026
Get there early, only one TSA line open and thew queue was very long.
AlejandroFlew with United Airlines
ORD
-
LNK
Apr 2026
expect some delays and be prepared, but once arrived to Lincoln, airport is very easy to navigate since it is very small. Prices are higher than other airports, but that is ok when looking for convenience.
IanFlew with American Airlines
ORD
-
DFW
Apr 2026
Lately ORD airport struggles in general often having ground stops. Construction extends travel back to airport so allow 2 hrs. Over past few months, experienced far few delays on United than AA.
SteveFlew with Spirit Airlines
ORD
-
MCO
Mar 2026
Bring a seat cushion if you're flying Spirit.
Verified travelerFlew with United Airlines
ORD
-
BOS
Apr 2026
Chicago airport is super chaotic. We had come in from an overseas flight and were required to get our checked bags at Baggage Claim and recheck them for our next flight, which took a while. Then after going through a LONG customs line (again) and rechecking my bag, I was told to take a shuttle to a different terminal for my final flight. Even though I never left the building and had no access to the outside world, I had to go through security AGAIN (boots off, dump out my water, wait in long lines…) My advice is to be sure you have at least a couple of hours between flights to deal with the insanity.
Verified travelerFlew with American Airlines
ORD
-
BUF
Apr 2026
travel to ohare is horror - work in extra time
Verified travelerFlew with ANA
ORD
-
EWR
Dec 2025
Give adequate time of more than 2 hours for your connection in Chicago O’Hare .. The terminals are not that far apart but still if it’s checked out and check in again process that involves TSA security screening again , 2 hours may not be enough ..
MarcoFlew with United Airlines
ORD
-
ORF
Dec 2025
United delayed my luggage twice on flight to Europe (first flight was for an important event) I carry 2 days of clothes in my backpack no matter who I'm flying with United especially so. No less than 2 hour layover to decrease possibility of loss/delay of luggage. Second EU trip my luggage was left in Germany even though my layover was just over 1 hour. Select layovers of 2+ hours although Unite will sell flights with 40 minutes layover (nonsense). 1 hour layover was not enough to transfer luggage in FRA. The last scan was 30 minutes after the flight left (SMH).
NikhilFlew with Air Canada
ORD
-
YYZ
Jul 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 Airlines
ORD
-
PIT
Jun 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 Airlines
ORD
-
LAS
Mar 2025
If you can select your seats in advance please do
AndreaFlew with United Airlines
ORD
-
ATL
May 2025
Ask for stewards to assist and provide amenities or you won’t get them.
Verified travelerFlew with American Airlines
ORD
-
TPA
Dec 2024
I recommend having movies and songs downloaded on your device.
Dr. JosephFlew with American Airlines
ORD
-
DFW
Jan 2025
Be very vigilant about the weather both in Chicago and in Dallas. Adverse weather in either area can affect the trip.
JanieFlew with SWISS
ORD
-
PHX
Feb 2025
I think you should prebook food or bring your own food.
valerieFlew with Air Canada
ORD
-
YUL
Jan 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 Airlines
ORD
-
LAS
Sep 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 Airlines
ORD
-
LAX
Sep 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 Airlines
ORD
-
PDX
Sep 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 Canada
ORD
-
YOW
Nov 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 Airways
ORD
-
CID
Sep 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 Airlines
MDW
-
YTZ
Sep 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
mauriceFlew with Iberia
ORD
-
JFK
Sep 2024
You should arrive early, take a lighht snack and be prepared for delays.
HeatherFlew with Lufthansa
ORD
-
MKE
Aug 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.
DianaFlew with American Airlines
ORD
-
IND
Jul 2024
Be sure to have name spelled correctly. Two hours early works well.
AlexanderFlew with Spirit Airlines
ORD
-
LGA
May 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 Airlines
ORD
-
PHX
Apr 2024
Use the find my gate feature on the flights phone app if available as the airport is a bit confusing
AyannaFlew with Spirit Airlines
ORD
-
TPA
May 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
PaulFlew with Alaska Airlines
ORD
-
SEA
Apr 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 Airlines
ORD
-
DSM
May 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 Airlines
ORD
-
SEA
Apr 2024
If you miss your flight ask any alaska agent to how and where to rebook the flight.
UzomaFlew with American Airlines
ORD
-
DCA
Jan 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 Airlines
ORD
-
MCO
Feb 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 Airlines
ORD
-
CLT
Jan 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 Airlines
ORD
-
YOW
Jan 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.

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.
7.9
SouthwestOverall score based on 4250 reviews
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

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

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The flight was delayed significantly. Communication during the flight was abrupt and caused some panic as we were navigating turbulence. It was also too loud and every announcement felt startling. The flight attendants did not offer any assurances and I felt unsettled most of the flight. The seats, floor and tray table was very dirty. The seat next to me was broken and the passenger sitting there was very uncomfortable. He had a spring in his back and his seat made terrible squeaking noises through the flight.

Significant delays on my trip to Chicago and my trip back to NY

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

I am disabled and was unable to get any assistance from Volaris. I had to wait in line at front desk for 45 minutes, I am by myself, and unable to stand. When I got to front desk check in, they had no assistance for me. I did however, have wheelchair assistance when I arrived in Mexico City. Thank God for that!

Our flight got overbooked and we missed one day of our trip.

Be prepared to pay extra for everything! I'm not sure I really saved any money?

The flight was 3 hrs delayed and no remorse from airline

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 !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

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

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

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.