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Find cheap flights from Chicago Midway Airport to North America from $48

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 9/8. 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
Tue 7/2
Tue 7/9

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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$112
Los Angeles
Los Angeles1 stop$178
Orlando
Orlandononstop$99
Las Vegas
Las Vegasnonstop$132
Miami
Miaminonstop$55
San Francisco
San Franciscononstop$138
Boston
Boston1 stop$116
Washington, D.C.
Baltimorenonstop$98
Denver
Denvernonstop$53
Seattle
Seattle1 stop$176
Fort Lauderdale
Fort Lauderdale1 stop$107
Atlanta
Atlantanonstop$56
Dallas
Dallasnonstop$58
Cancún
Cancún1 stop$293
Tampa
Tampanonstop$100
Houston
Houstonnonstop$62
Honolulu
Honolulu2 stops$432
Toronto
Torontononstop$245

Good to know

Low season

January

High season

March

Cheapest flight

$48
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Chicago Midway Airport to Orlando 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 $72 one-way - $138 round-trip; Denver $49 one-way - $88 round-trip; Orlando $77 one-way - $151 round-trip
  • Morning departure is around 6% more expensive 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 10410 reviews
8.2Boarding
7.9Comfort
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

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 flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

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!

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

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.

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?

Check in at LAX was terrible. Unbelievable lines. Chaos. The landing in Morelia was scary, with the plane fishtailing. If other airlines flew directly between California and Morelia, I would never fly Volaris again.

Viva Aerobus Is honesto the worst airline and I don't think I'll fly with them ever again.

The flight was 3 hrs delayed and no remorse from airline

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

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

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

Book cheap flights from Chicago to North America

Recent round-trip flight deals

8/17Sat
nonstopFrontier
2h 41mMDW-MCO
8/22Thu
nonstopFrontier
2h 48mMCO-MDW
$99
10/21Mon
nonstopFrontier
2h 41mMDW-MCO
10/25Fri
nonstopFrontier
2h 48mMCO-MDW
$100
9/14Sat
1 stopDelta
4h 09mMDW-EWR
9/21Sat
1 stopDelta
6h 44mEWR-MDW
$156
8/24Sat
1 stopDelta
4h 28mMDW-EWR
8/27Tue
1 stopDelta
5h 07mEWR-MDW
$187
6/14Fri
1 stopAllegiant Air
4h 30mMDW-MCO
6/17Mon
1 stopAllegiant Air
7h 31mMCO-MDW
$220
7/12Fri
1 stopAllegiant Air
10h 58mMDW-EWR
7/15Mon
1 stopAllegiant Air
10h 22mEWR-MDW
$231
10/28Mon
1 stopVolaris
8h 52mMDW-MEX
11/4Mon
1 stopVolaris
6h 31mMEX-MDW
$405
11/24Sun
1 stopVolaris
12h 05mMDW-MEX
11/30Sat
1 stopVolaris
12h 47mMEX-MDW
$417
6/14Fri
1 stopPorter Airlines
9h 45mMDW-EWR
6/16Sun
2 stopsPorter Airlines
8h 27mEWR-MDW
$490
7/3Wed
1 stopPorter Airlines
6h 07mMDW-BOS
7/8Mon
1 stopPorter Airlines
14h 22mBOS-MDW
$491

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Recent one-way flight deals

9/8Sun
nonstopFrontier
2h 41mMDW-MCO
$48
8/31Sat
nonstopFrontier
2h 41mMDW-MCO
$49
8/7Wed
1 stopDelta
5h 06mMDW-EWR
$78
10/15Tue
1 stopDelta
5h 14mMDW-EWR
$94
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$103
7/1Mon
1 stopAllegiant Air
4h 30mMDW-MCO
$105
8/1Thu
1 stopPorter Airlines
6h 30mMDW-EWR
$233
7/18Thu
1 stopPorter Airlines
5h 20mMDW-EWR
$246
6/25Tue
1 stopVolaris
13h 00mMDW-MEX
$253
7/2Tue
1 stopVolaris
12h 15mMDW-MEX
$254

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Last minute flights from Midway to North America

Last minute flight, train and bus deals

6/6Thu
multi-stopFrontier
10h 25mMDW-BOS
6/12Wed
multi-stopFrontier
14h 40mBOS-MDW
$149
6/4Tue
nonstopFrontier
4h 10mMDW-LAS
6/11Tue
nonstopFrontier
3h 33mLAS-MDW
$151
6/4Tue
nonstopFrontier
4h 10mMDW-LAS
6/11Tue
nonstopFrontier
3h 33mLAS-MDW
$152
6/4Tue
multi-stopDelta
7h 13mMDW-BOS
6/8Sat
multi-stopDelta
4h 28mBOS-MDW
$334
6/4Tue
multi-stopDelta
7h 13mMDW-BOS
6/6Thu
multi-stopDelta
4h 31mBOS-MDW
$356
6/3Mon
multi-stopAllegiant Air
5h 00mMDW-MCO
6/7Fri
multi-stopAllegiant Air
6h 57mMCO-MDW
$393
6/7Fri
multi-stopVolaris
13h 00mMDW-MEX
6/14Fri
multi-stopVolaris
12h 52mMEX-MDW
$658
6/7Fri
multi-stopVolaris
13h 00mMDW-MEX
6/14Fri
multi-stopVolaris
12h 52mMEX-MDW
$693
6/5Wed
multi-stopPorter Airlines
19h 15mMDW-EWR
6/12Wed
multi-stopPorter Airlines
16h 42mEWR-MDW
$800
6/6Thu
multi-stopPorter Airlines
5h 20mMDW-EWR
6/8Sat
multi-stopPorter Airlines
22h 07mEWR-MDW
$864

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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:

$639
$728
$477
$37