$86 Find Cheap Flights from Chicago Midway Airport 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 Midway to North America departing on 7/14. 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 Midway to North America

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New Yorknonstop$187
Orlando
Orlando1 stop$191
Los Angeles
Los Angeles1 stop$240
Las Vegas
Las Vegas1 stop$235
San Francisco
San Francisco1 stop$299
Miami
Miami2 stops$192
Boston
Bostonnonstop$179
Fort Lauderdale
Fort Lauderdalenonstop$171
Washington, D.C.
Baltimore1 stop$235
Denver
Denvernonstop$205
Seattle
Seattle1 stop$343
Atlanta
Atlantanonstop$106
Dallas
Dallasnonstop$145
Tampa
Tampa1 stop$206
Houston
Houstonnonstop$209
Cancún
Cancún1 stop$366
San Diego
San Diego1 stop$292
Honolulu
Honolulu1 stop$674
New York
New Yorknonstop$187
Orlando
Orlando1 stop$191
Los Angeles
Los Angeles1 stop$240
Las Vegas
Las Vegas1 stop$235
San Francisco
San Francisco1 stop$299
Miami
Miami2 stops$192
Boston
Bostonnonstop$179
Fort Lauderdale
Fort Lauderdalenonstop$171
Washington, D.C.
Baltimore1 stop$235
Denver
Denvernonstop$205
Seattle
Seattle1 stop$343
Atlanta
Atlantanonstop$106
Dallas
Dallasnonstop$145
Tampa
Tampa1 stop$206
Houston
Houstonnonstop$209
Cancún
Cancún1 stop$366
San Diego
San Diego1 stop$292
Honolulu
Honolulu1 stop$674

Book Cheap Midway 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 Midway 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 Midway to North America

Tue, Aug 11 - Sat, Aug 15
Frontier Logo
5:46 pm - 8:20 pm
MDW
-
DFW
2h 34mnonstop
Frontier Logo
3:01 pm - 5:26 pm
DFW
-
MDW
2h 25mnonstop
$145Frontier
Sat, Aug 1 - Wed, Aug 12
Frontier Logo
6:41 pm - 9:21 pm
MDW
-
DFW
2h 40mnonstop
Frontier Logo
1:30 pm - 3:50 pm
DFW
-
MDW
2h 20mnonstop
$146Frontier
Tue, Aug 4 - Wed, Aug 12
Frontier Logo
5:46 pm - 8:20 pm
MDW
-
DFW
2h 34mnonstop
Frontier Logo
1:30 pm - 3:50 pm
DFW
-
MDW
2h 20mnonstop
$150Frontier
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
8:35 am - 12:40 pm
MDW
-
FLL
3h 05mnonstop
Southwest Logo
7:20 am - 9:20 am
FLL
-
MDW
3h 00mnonstop
$171Southwest
Wed, Jul 22 - Wed, Jul 29
Southwest Logo
11:15 am - 5:15 pm
MDW
-
FLL
5h 00m
1 stop
Southwest Logo
12:20 pm - 2:20 pm
FLL
-
MDW
3h 00mnonstop
$177Southwest
Wed, Aug 19 - Wed, Aug 26
Southwest Logo
6:10 pm - 10:05 pm
MDW
-
FLL
2h 55mnonstop
Southwest Logo
4:45 pm - 9:00 pm
FLL
-
MDW
5h 15m
1 stop
$181Southwest
Wed, Jul 15 - Tue, Jul 21
Southwest Logo
7:50 am - 4:20 pm
MDW
-
FLL
7h 30m
2 stops
Southwest Logo
5:50 pm - 7:55 pm
FLL
-
MDW
3h 05mnonstop
$182Southwest
Tue, Jul 21 - Wed, Jul 22
Delta Logo
6:00 am - 12:21 pm
MDW
-
EWR
5h 21m
1 stop
Delta Logo
1:00 pm - 6:25 pm
EWR
-
MDW
6h 25m
1 stop
$207Delta
Thu, Aug 13 - Tue, Aug 18
Delta Logo
6:42 pm - 11:25 pm
MDW
-
EWR
3h 43m
1 stop
Delta Logo
6:00 am - 9:17 am
EWR
-
MDW
4h 17m
1 stop
$215Delta
Sat, Aug 15 - Wed, Aug 19
Delta Logo
9:24 am - 3:59 pm
MDW
-
EWR
5h 35m
1 stop
Delta Logo
6:00 am - 11:51 am
EWR
-
MDW
6h 51m
1 stop
$217Delta
Booking Insights

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

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

What is the cheapest Chicago Midway Airport 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 Midway Airport found in the last 5 days was to Atlanta, at $112 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Atlanta (ATL), and the cheapest round-trip airline ticket found on this route in the last 5 days was $112.

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

The average price for all round-trip flights from Chicago Midway Airport 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 in the evening, when round-trip flights cost $215 on average. Morning departures are around 10% more expensive 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 $350.

Can I save money by flying with a layover from Chicago Midway Airport 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 $414, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport 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 Midway Airport 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 Midway Airport to North America is January, when tickets cost $236 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $392 and $392 respectively.

Good to know

Low seasonJanuary
Cheapest flight$86
Most popular time to fly with an average 15% increase in price.
Flight from Chicago Midway Airport to Fort Lauderdale

FAQs - booking North America flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport 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 Midway Airport to North America.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport to North America up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to North America

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Atlanta $135 one-way - $220 round-trip; New York $131 one-way - $262 round-trip; Orlando $162 one-way - $338 round-trip

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

 
Need help choosing which airline to fly with from Midway 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 4239 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

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.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

Seats were very uncomfortable and being charged for snacks and water.........

Allegiant actually impressed me, original inbound flight from PBG was so late they gave us a bird inbound from Des Moines and only left 1h late and gained 40 minutes back in the air. Comfortable flight with no frills but no complaints.

Flight was delayed. Crew was good but hot coffee was not available.

Great. No choice for n/a. No food or entertainment options

No food is available without purchasing it and there is no in-flight entertainment. Both of these are OK because we got an inexpensive flight from Allegiant and, otherwise, our experience was excellent.

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

It was cold on the flight. The crew was very pleasant. I didn't order any food. We were delayed due to Captain waiting on maintenance log. He kept us informed though. The flight itself was smooth. I would definitely fly with Allegiant again!

I had a fantastic experience with Allegiant. I had wheelchair assistance and they helped me find my luggage and brought me to my car. Even loaded my luggage. Wonderful service!! Thank you Allegiant!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

The flights were on time, the ground crew and on board crews were kind and efficient. The free snacks for Premium+ were good, similar to US First Class snacks. The plane were clean and bright! Complaints? The seats were worn and the seat-back pockets were missing. Overall, I'll book again with Volaris. Ignore the negative social media posts, understand what your fare includes, buy the add ons you need. We had no problems with our personal items and carryons.

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

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

The money you save flying volaris is not worth it

Is was a good short flight with some turbulence! I would fly Volaris again.

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

Unfortunately it was not a good flight got canceled had to be at the airport all night long to get a different flight to another airport my first flight with Volaris was very bad. Poor services

The boarding , and it would be nice if they would let us know head of time about flight changes

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

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

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

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.

Everything you need to know for your flight to North America

Information on your arrival and departure airports