$53 Find Cheap Flights from Chicago Midway Airport 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 Midway to North America departing on 7/1. 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

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Flights Deals

Best North America Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
New York
New Yorknonstop$125
Los Angeles
Los Angeles1 stop$187
Orlando
Orlandononstop$126
Las Vegas
Las Vegasnonstop$146
Miami
Miaminonstop$137
San Francisco
San Franciscononstop$179
Boston
Bostonnonstop$123
Washington, D.C.
Baltimorenonstop$97
Denver
Denvernonstop$129
Seattle
Seattlenonstop$109
Fort Lauderdale
Fort Lauderdalenonstop$157
Atlanta
Atlantanonstop$97
Dallas
Dallasnonstop$129
Tampa
Tampanonstop$157
Houston
Houstonnonstop$146
Cancún
Cancúnnonstop$269
Honolulu
Honolulu1 stop$465
San Diego
San Diegononstop$161
New York
New Yorknonstop$125
Los Angeles
Los Angeles1 stop$187
Orlando
Orlandononstop$126
Las Vegas
Las Vegasnonstop$146
Miami
Miaminonstop$137
San Francisco
San Franciscononstop$179
Boston
Bostonnonstop$123
Washington, D.C.
Baltimorenonstop$97
Denver
Denvernonstop$129
Seattle
Seattlenonstop$109
Fort Lauderdale
Fort Lauderdalenonstop$157
Atlanta
Atlantanonstop$97
Dallas
Dallasnonstop$129
Tampa
Tampanonstop$157
Houston
Houstonnonstop$146
Cancún
Cancúnnonstop$269
Honolulu
Honolulu1 stop$465
San Diego
San Diegononstop$161

Cheap Flights from Midway to North America

 
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

Sat, Jul 19 - Tue, Jul 22
Frontier Logo
6:20 am - 9:25 amMDW-ATL
2h 05mnonstop
Frontier Logo
9:37 am - 10:40 amATL-MDW
2h 03mnonstop
$97Frontier
Find Deal
Tue, Jul 15 - Tue, Jul 22
Frontier Logo
11:39 am - 2:45 pmMDW-ATL
2h 06mnonstop
Frontier Logo
9:37 am - 10:40 amATL-MDW
2h 03mnonstop
$98Frontier
Find Deal
Tue, Aug 19 - Tue, Aug 26
Southwest Logo
9:05 pm - 11:35 pmMDW-SEA
4h 30mnonstop
Southwest Logo
5:35 am - 11:30 amSEA-MDW
3h 55mnonstop
$109Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 16
Southwest Logo
5:25 pm - 7:55 pmMDW-SEA
4h 30mnonstop
Southwest Logo
5:35 am - 11:30 amSEA-MDW
3h 55mnonstop
$117Southwest
Find Deal
Sat, Jul 12 - Tue, Jul 15
Delta Logo
4:22 pm - 7:26 pmMDW-ATL
2h 04mnonstop
Delta Logo
8:46 pm - 9:42 pmATL-MDW
1h 56mnonstop
$161Delta
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Wed, Sep 10 - Sat, Sep 13
Delta Logo
6:00 am - 12:11 pmMDW-EWR
5h 11m1 stop
Delta Logo
5:30 pm - 9:44 pmEWR-MDW
5h 14m1 stop
$163Delta
Find Deal
Fri, Aug 1 - Sun, Aug 3
Allegiant Air Logo
1:11 pm - 9:05 amMDW-EWR
18h 54m1 stop
Allegiant Air Logo
9:55 am - 12:21 pmEWR-MDW
27h 26m1 stop
$203Allegiant Air
Find Deal
Fri, Jul 18 - Sun, Jul 20
Allegiant Air Logo
10:31 am - 9:05 amMDW-EWR
21h 34m1 stop
Allegiant Air Logo
9:55 am - 9:41 amEWR-MDW
24h 46m1 stop
$225Allegiant Air
Find Deal
Sat, Aug 9 - Mon, Aug 11
Volaris Logo
8:39 pm - 9:40 amMDW-MEX
14h 01m1 stop
Volaris Logo
6:00 am - 7:16 pmMEX-MDW
12h 16m1 stop
$478Volaris
Find Deal
Thu, Nov 13 - Mon, Nov 17
Volaris Logo
8:39 am - 7:45 pmMDW-MEX
11h 06m1 stop
Volaris Logo
6:00 am - 5:34 pmMEX-MDW
11h 34m1 stop
$499Volaris
Find Deal
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to North America.

The cheapest ticket to North America from Chicago Midway Airport found in the last 72 hours was to Atlanta, at $102 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 72 hours was $102.

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 $334, 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 September, when tickets cost $207 (return) on average. On the other hand, the most expensive months are December and August, when the average cost of round-trip tickets is $379 and $308 respectively.

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

The average price of all round-trip flights from Chicago Midway Airport 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 Saturday and more expensive on a Thursday. On your return trip to Chicago Midway Airport, you should consider flying back on a Tuesday, and avoid Sundays for better deals.


Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$53
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago Midway Airport to New York LaGuardia Airport

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.

  • 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 $242 on average. Morning departures are around 4% 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 $267.

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 $125 one-way - $172 round-trip; Denver $98 one-way - $179 round-trip; Orlando $92 one-way - $232 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.
8.0
SouthwestOverall score based on 4280 reviews
8.0Comfort
8.2Boarding
7.1Food
8.6Crew
7.6Entertainment
Airline reviews

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

2.0 MediocreKristina, Jun 2025BOS - DEN
Read more Southwest reviews

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

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

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

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.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

They canceled flight. Hard to believe there was even a plane incoming for us to get on

The worst. We never made our connection and they did absolutely nothing to help us at the airport.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. The flight was delayed due to an attendant forgetting to come to work. On the flight no drinks were offered only for purchase meals.

No way to get boarding pass on my phone. In order to print the bag ticket a boarding pass is needed. Asked the agent to print me one, they said they typically do not due this as its so much work. I showed the email confirmation and I asked how i could do it my self the agent replied he did not know as there was no link. On the flight no drinks were offered only for purchase meals.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

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