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$42 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 9/9. 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
0 bags
sáb 8/24
sáb 8/31

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Best North America Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

New York
New York1 stop$106
Los Angeles
Los Angeles1 stop$141
Orlando
Orlandononstop$90
Las Vegas
Las Vegasnonstop$88
Miami
Miaminonstop$60
San Francisco
San Franciscononstop$90
Boston
Boston1 stop$101
Washington, D.C.
Baltimorenonstop$58
Denver
Denvernonstop$68
Seattle
Seattle1 stop$146
Fort Lauderdale
Fort Lauderdale1 stop$101
Atlanta
Atlantanonstop$47
Dallas
Dallasnonstop$51
Cancún
Cancún1 stop$221
Tampa
Tampanonstop$88
Houston
Houstonnonstop$63
Honolulu
Honolulu1 stop$422
Toronto
Torontononstop$237

Good to know

Low season

January

High season

July

Cheapest flight

$42
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from Chicago Midway Airport to Dallas/Fort Worth 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 to North America from Chicago Midway Airport 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 to North America with an airline and back to Chicago Midway Airport 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 to North America from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $78 one-way - $147 round-trip; Denver $51 one-way - $86 round-trip; Tampa $50 one-way - $96 round-trip
  • Morning departure is around 4% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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
DeltaOverall score based on 9630 reviews
8.2Boarding
8.0Entertainment
8.6Crew
7.4Food
7.9Comfort
Airline reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

6.0 GoodKathy, Jul 2024ANC - SLC
Read more about Delta reviews

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

Flight for canceled. Horrible experience.. had to rent a car to drive myself up here.

Flights were terribly delayed. I was at At,anta Airport for over 4 hours waiting for my connection.

My flight consistently said it was on time and the plane didn’t arrive until after 30 minutes after take off and nothing was announced to passengers

The flight was canceled two hours before departure, it took over five hours to rebook us on another flight.

First, the flight was schedule to leave at 12:08. Delayed to 12:38. It is 12:58 and I am sitting at the gate. The staff are not communicating with us (just tell me it’s gonna be five hours if that’s the case, quit hufflepuffing around like you’re trying to board us when the plane isn’t even here and you don’t know where your crew are. I’m still waiting for any communication about the further delay. This is a rebooked flight from a cancelled flight yesterday, when the airline failed to fulfill its fiduciary responsibility to hotel and cover transport for overnight cancelations. Asking about the food on the flight? What food?!? Delta doesn’t serve meals unless you pay for them and you really want me to give delta a high rating for passing out processed snacks (fun size!)? Can we be for real. Delta is cementing itself in history as one of the cheap, stingy, outdated, glory days are over airlines, and it shows. I took this flight knowing delta was going to provide below level service but this is beyond burgers!! I can’t believe a multi billion or dollar company looked straight in my eyes yesterday and I told me this wasn’t their fault and there for the extra cost in hotel and hundreds of dollars in Ubers are MY RESPONSIBILITY. The only thing I am at fault for is believing delta is reputable company worthy of my dollars. I’m not even sure I want to be compensated unless it is cash because I would rather die never traveling again than to put money in their pockets.

The flight was great. The crew were a little terse about the size of my bag. It fit fine.

I know it was not in Deltas fault. But numerous delays and cancelations. I requested a hotel voucher and was told they weren't available. The lady on my hotel shuttle did receive one from American. Why the difference?

Flight was delayed. Had to get rebooked. Diamond medallion but stuck in a crappy seat. Rebooked flight then got delayed again. Then when we finally boarded, we waited another hour for a new crew. Then landed in JFK and sat for another 40 minutes waiting for a crew to come to the gate to be able to deplane. Hot mess all around, which unfortunately is becoming the norm for Delta

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

Wish we had music during take off and landing like the last flight

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

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.

Posted a 20minute delay but didn’t delay at all. Caused boarding issues and confusion. Also, didn’t release baggage. Took over an hour and 20 minutes to get luggage.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

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;(

When booking I was not made aware that my flight would be standby. I was told when checking my bags that I purchased standby tickets. Luckily there was enough room but an unpleasant experience to say the least.

The WiFi tv wasn’t working. The flight was over sold and moved several times. The gate assignment appeared on the screens right as we were supposed to board. Because of the flight being over sold we were almost stuck in Cancun for a couple of a days. The flight attendants were unfriendly and would wake you up to pick up other people’s trash.

For the price, you pretty much can't beat this airlines. As far as comfort, you could do a lot better, but it'll cost you. Over all cheapest way to get from point A to point B.

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!

It was horrible, our flight back was overbooked and had to take a flight 12hours later in the day but to LAX. Volaris is horrible.

When you make the 3 Lines to board de airplane , I believe that you should make only one line first and then call the next and then last ,,, because the number 3 wait to long just standing there ,, my opinion !!!

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?

Better than expected.on time. Friendly staff in NY however MYR not so nice.

The flight crew and flight attendants are poorly trained and demonstrate poor professionalism. They have a sloppy appearance and communicate with patrons poorly. It is embarrassing for them to be representatives of an airline and for them to be called professionals.

After 5 hours of delay, they cancelled the flight. Very disappointed

My flight to LA was cancelled. I waited at the airport for 3 hrs saying it was delayed and then all of a sudden it was cancelled. Frontier only gave me a voucher and refund but could not rebook me. Flights on other airlines were too expensive last minute. I had to drive down to LA and didn’t even take my return flight home since I had to drive. One of the worst airline experiences in my life. It’s crazy how airlines can just upend people’s plans just like that.

Flying Frontiier was extremely poor!! I paid for a7:15am flight on flight 1601 from PHL To Las Vegas and the delay was brutally, excruciatingly and disgustingly long (8 hrs). I arrived by Uber to PHL at 5:30 am and had to spend the entire 8 hr delay inside the airport. Even more atrocious was that the flight was delayed twice. On the phone with customer service for two hours and was not fully compensated. I feel taken advantage of with this airline. They offered a menial couched for another flight within 90 days to me and my husband who has never flown but this experience has made us almost 100% sure to not fly this airline and will suggest that others don’t either. We don’t want to book ever again, don’t want a menial voucher and I believe by standard and because the flight was delayed for 8 hours, I should be fully reimbursed for the entire round trip. There is no excuse why this should have ever occurred. After sharing my experience with others in Vegas and Philadelphia, I was told that Frontier airlines is notorious for long delayed flights, poor customer service and refusal to compensate people correctly. I’m very nervous to see what departing from Vegas to Philadelphia will bring.

I fly Frontier often and generally don't have any issues. For some reason, the Denver to Houston's George Bush Intercontinental (IAH) flight always needs to wait on the tarmac in Houston because a gate is not available after landing. I've been stuck for as little as 15 minutes and as much as a little over an hour. I know only fly the Frontier Denver to IAH route when there is not an available flight to Houston Hobby (HOU).

Flight was 3 hours late leaving. Poor communication from the staff about delays. Impossible to get in touch with customer service (by design). And it actually didn't come out to be much cheaper than a non-budget airline! Not worth the headache, I'm never flying Frontier again

I’ve never flown frontier without a flight getting canceled. I understand that things go wrong with planes, but all other airlines handle cancellations so well. Frontier becomes a dumpster fire if a problem appears for them.

Checking in was easy and simple, crew was nice and efficient, but I would improve seat assignment randomness to make it easier to sit together based on when you check in. Overall would fly with them again.

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

Book cheap flights from Chicago to North America

Recent round-trip flight deals

8/17sáb
nonstopFrontier
2h 03mMDW-ATL
8/21qua
nonstopFrontier
2h 05mATL-MDW
$50
10/26sáb
nonstopFrontier
2h 28mMDW-DFW
10/26sáb
nonstopFrontier
2h 22mDFW-MDW
$51
9/21sáb
nonstopDelta
1h 55mMDW-ATL
9/23seg
nonstopDelta
1h 53mATL-MDW
$119
9/24ter
nonstopDelta
1h 54mMDW-ATL
9/25qua
nonstopDelta
1h 53mATL-MDW
$132
8/19seg
nonstopSouthwest
2h 20mMDW-BOS
8/22qui
nonstopSouthwest
2h 40mBOS-MDW
$209
8/23sex
nonstopSouthwest
2h 10mMDW-LGA
8/30sex
nonstopSouthwest
2h 20mLGA-MDW
$213
10/28seg
1 stopVolaris
8h 52mMDW-MEX
10/31qui
1 stopVolaris
12h 37mMEX-MDW
$382
9/27sex
1 stopVolaris
13h 00mMDW-MEX
9/30seg
1 stopVolaris
10h 22mMEX-MDW
$386
8/21qua
1 stopPorter Airlines
14h 00mMDW-EWR
8/28qua
1 stopPorter Airlines
10h 27mEWR-MDW
$427
9/13sex
1 stopPorter Airlines
7h 30mMDW-EWR
9/20sex
1 stopPorter Airlines
14h 47mEWR-MDW
$434

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Recent one-way flight deals

9/9seg
nonstopFrontier
2h 26mMDW-DFW
$42
8/18dom
nonstopFrontier
2h 03mMDW-ATL
$42
8/22qui
nonstopDelta
1h 58mMDW-ATL
$60
8/13ter
1 stopDelta
4h 28mMDW-EWR
$78
8/9sex
1 stopAllegiant Air
19h 51mMDW-EWR
$91
9/27sex
1 stopAllegiant Air
13h 55mMDW-EWR
$102
8/15qui
1 stopVolaris
17h 40mMDW-MEX
$122
8/30sex
1 stopVolaris
22h 20mMDW-MEX
$173
9/15dom
1 stopPorter Airlines
5h 50mMDW-EWR
$226
9/29dom
1 stopPorter Airlines
8h 00mMDW-EWR
$227

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Last minute flights from Midway to North America

Last minute flight, train and bus deals

7/30ter
nonstopFrontier
2h 00mMDW-ATL
8/17sáb
nonstopFrontier
2h 06mATL-MDW
$123
7/30ter
nonstopFrontier
2h 00mMDW-ATL
8/15qui
nonstopFrontier
2h 05mATL-MDW
$128
7/30ter
multi-stopDelta
4h 58mMDW-EWR
8/6ter
multi-stopDelta
3h 33mEWR-MDW
$278
7/29seg
nonstopSouthwest
2h 05mMDW-LGA
8/1qui
nonstopSouthwest
2h 25mLGA-MDW
$325
7/27sáb
multi-stopDelta
6h 05mMDW-EWR
8/3sáb
multi-stopDelta
3h 33mEWR-MDW
$326
7/29seg
nonstopSouthwest
2h 05mMDW-LGA
8/1qui
multi-stopSouthwest
11h 45mLGA-MDW
$335
7/29seg
multi-stopVolaris
11h 47mMDW-MEX
8/2sex
multi-stopVolaris
11h 02mMEX-MDW
$537
7/28dom
multi-stopVolaris
13h 00mMDW-MEX
8/28qua
multi-stopVolaris
11h 02mMEX-MDW
$593
7/28dom
multi-stopPorter Airlines
14h 00mMDW-EWR
8/6ter
multi-stopPorter Airlines
16h 42mEWR-MDW
$777
7/30ter
multi-stopPorter Airlines
10h 05mMDW-EWR
8/3sáb
multi-stopPorter Airlines
9h 52mEWR-MDW
$784

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Chicago Midway Airport - North America Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

North America - Chicago Midway Airport

Cabin classes:

$438
$606
$424
$39