$39 Find Deals on Flights from Chicago Midway Airport

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 Worldwide departing on 6/8. 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.
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Flights Deals

Find Cheap Flights from Chicago Midway Airport

Where can I fly from Chicago Midway Airport?Prices from MDW, departing Sat 5/31 and returning Sat 6/7

Book Cheap International Flights Deals from Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway 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.

Recent round-trip international flight deals from Midway

KAYAK's recommended round-trip international deals departing in the coming months from the most popular airlines that fly from Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
6:20 am - 9:25 amMDW-ATL
2h 05mnonstop
Frontier Logo
9:30 pm - 10:35 pmATL-MDW
2h 05mnonstop
$76Frontier
Find Deal
Sat, Aug 9 - Sat, Aug 16
Frontier Logo
6:35 am - 9:54 amMDW-ATL
2h 19mnonstop
Frontier Logo
2:33 pm - 3:39 pmATL-MDW
2h 06mnonstop
$77Frontier
Find Deal
Tue, May 27 - Tue, Jun 3
Southwest Logo
8:20 pm - 11:25 pmMDW-LGA
2h 05mnonstop
Southwest Logo
6:10 am - 7:30 amLGA-MDW
2h 20mnonstop
$137Southwest
Find Deal
Wed, May 14 - Wed, May 28
Southwest Logo
5:15 am - 6:50 amMDW-DEN
2h 35mnonstop
Southwest Logo
9:30 pm - 12:55 amDEN-MDW
2h 25mnonstop
$151Southwest
Find Deal
Tue, Jul 15 - Wed, Jul 16
Delta Logo
10:35 am - 1:29 pmMDW-ATL
1h 54mnonstop
Delta Logo
8:55 am - 9:51 amATL-MDW
1h 56mnonstop
$159Delta
Find Deal
Wed, Aug 20 - Wed, Aug 27
Delta Logo
5:53 pm - 11:00 pmMDW-EWR
4h 07m1 stop
Delta Logo
7:05 am - 11:59 amEWR-MDW
5h 54m1 stop
$179Delta
Find Deal
Sat, Jun 21 - Tue, Jun 24
 Logo
8:04 pm - 11:05 amMDW-EWR
14h 01m1 stop
 Logo
11:04 am - 8:47 amEWR-MDW
22h 43m1 stop
Fri, May 30 - Fri, Jun 6
Allegiant Air Logo
8:04 pm - 11:05 amMDW-EWR
14h 01m1 stop
Allegiant Air Logo
9:55 am - 2:03 pmEWR-MDW
5h 08m1 stop
$202Allegiant Air
Find Deal
Fri, May 30 - Fri, Jun 6
 Logo
9:12 am - 11:37 pmMDW-LAS
16h 25m1 stop
 Logo
9:19 am - 2:56 pmLAS-MDW
3h 37mnonstop
Mon, Jun 16 - Fri, Jun 20
Allegiant Air Logo
8:04 pm - 9:05 amMDW-EWR
12h 01m1 stop
Allegiant Air Logo
12:55 pm - 8:22 amEWR-MDW
20h 27m1 stop
$222Allegiant Air
Find Deal
Mon, Jun 2 - Thu, Jun 5
Useful Info

KAYAK's insights & trends for flights from Midway

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

Which are the most popular places to fly to from Chicago Midway Airport?

The domestic destinations KAYAK users have most searched for when searching for flights from Chicago Midway Airport.
Based on KAYAK flight searches, the most popular place to fly from Midway is New York (19% of total searches). The next most popular destinations are Dallas (9%) and Las Vegas Harry Reid Intl (6%).

What are the most popular international flights out of Chicago Midway Airport?

The international destinations KAYAK users have most searched for when searching for flights from Chicago Midway Airport.
There are many international destinations you can fly to from Chicago Midway Airport. The most popular international destinations among KAYAK users are Paris, Tokyo and Rome.

What are the most popular countries to fly to from Chicago Midway Airport?

The most popular countries KAYAK users have searched for from Chicago Midway Airport along with the average round-trip price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most popular country to fly to from Chicago Midway Airport is Mexico (65% of total searches). The next most popular destinations are Canada (28%) and Jamaica (3%).

Which cities can I fly to direct from Chicago Midway Airport?

There are loads of places you can fly direct to from Chicago Midway Airport. The most popular destinations for direct flights among KAYAK users are Jacksonville, Los Angeles, El Paso, Charlotte and St. Louis. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Jacksonville at $189, while the most expensive was El Paso, at $321.

Which international cities can I fly to direct from Chicago Midway Airport?

There are many international destinations you can fly to non-stop from Chicago Midway Airport. The most popular international destinations from KAYAK users are Guadalajara, Morelia, León, Cancún and Toronto. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Toronto at $195, while the most expensive was Cancún, at $286.

What is the longest direct flight from Chicago Midway Airport?

The longest direct flight you can take from Chicago Midway Airport is to San José del Cabo, with a duration of 4h 50m. The next longest is Oakland at 4h 40m, followed by a flight to San Francisco at 4h 40m.

Good to know

Low seasonSeptember
High seasonApril
Cheapest flight$39
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago Midway Airport to Dallas/Fort Worth Airport

Flights from Midway: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew from Midway to anywhere 
Verified travelerFlew with Porter AirlinesMDW-YTZSep 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
SarahFlew with SouthwestMDW-AUSAug 2024
Midway airport is pleasant and not chaotic at all. Breezed through customs. Very good experience.
FreddyFlew with SouthwestMDW-LGAJul 2024
On a stormy day, be prepare for delays.
MusarratFlew with SouthwestMDW-JAXMay 2024
Southwest is best airline and Midway is also good airport in Chicago
ANAFlew with FrontierMDW-PHXMar 2024
More organization and more staff, there was a lot from diferentes cities coming at the airport, so it was a mess because people don’t understand. Or don’t want to understand the instrucción of wait in their seats…. So more staff could be helpful..

FAQs for booking flights out of Chicago Midway Airport

  • Are there any airlines that operate flights from Chicago Midway International Airport (MDW) and are known for being environmentally friendly?

    If being environmentally friendly is one of your priorities, you may want to fly with Delta. Delta has a goal to replace 10% of its standard aviation fuel with sustainable aviation fuel by the end of 2030.

  • How can I go from downtown Chicago to Chicago Midway International Airport (MDW)?

    To go from downtown Chicago to Chicago Midway International Airport (MDW), you can always choose to drive, which normally takes around 20 minutes in total. Public transportation is a convenient option as well, like bus line 55, which will bring you to the airport in around 10 to 15 minutes depending on how traffic is at the time.

  • Are there any airlines that have lounges for passengers at Chicago Midway International Airport (MDW)?

    There are no airlines that currently have lounges at Chicago Midway International Airport (MDW). However, the airport does have a USO Midway Lounge, which is reserved for past and present members of the military, as well as their family members. In this lounge, travelers will have access to free snacks and drinks, as well as shower facilities.

  • What services does Chicago Midway International Airport (MDW) offer for travelers with limited mobility or disabilities?

    Chicago Midway International Airport (MDW) has wheelchairs that all guests are able to use for free. The airport also has accessible restroom stalls, elevators, and ramps that can be used to go to different floors and terminals. If you will need additional help navigating the airport, make sure to contact your airline in advance.

  • What is Midway also known as?

    Chicago Midway Airport’s airport code is MDW. It can also be referred to as Chicago Midway, Chicago Midway Intl, Midway, Midway Intl.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport?

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight 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?

    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 your destination 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding a cheap flight out of Chicago Midway Airport

  • 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 $97 one-way - $169 round-trip; Denver $94 one-way - $184 round-trip; Orlando $99 one-way - $214 round-trip
  • Depending on how long your flight from Chicago Midway International Airport (MDW) will be, you may want to consider upgrading your ticket. Long-haul flights, such as those that go across the country or internationally, are often more enjoyable with extra legroom and perks. Many airlines will give you a special price to upgrade your ticket once you have made your reservation.
  • If you will be checking a substantial amount of luggage for your flight departing from Chicago Midway International Airport (MDW), you may want to consider flying with Southwest. Southwest allows all customers to check up to two bags at no additional cost.
  • Those embarking on a short flight may want to stick to bringing carry-on items. If your flight from Chicago Midway International Airport (MDW) is operated by companies such as Alaska Airlines or Delta, you will typically be able to bring one personal item and one carry-on bag for free.
  • To help save money on your flight from Chicago Midway International Airport (MDW), you may want to choose an Economy Light ticket type, rather than traditional Economy. For example, Virgin Atlantic offers these types of tickets for many of its routes.
  • For some routes that depart from Chicago Midway International Airport (MDW), you may have a layover before reaching your destination. You will find that it is quite common to change planes in cities such as Atlanta and Miami, as they are both major travel hubs.

Top 5 airlines serving from Midway to Worldwide

Need help choosing which airline to fly with from Midway to Worldwide? 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 4293 reviews
7.1Food
8.2Boarding
8.6Crew
7.6Entertainment
8.0Comfort
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Flight was delayed due to weather. Crew did a nice job of making us comfortable. No complain complaints.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

It was an overnight flight and I desperately needed coffee before we landed, but Delta does only one beverage service, and that is shortly after takeoff, not before landing at 5 am.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

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.

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.

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.

They were only able to give me a seat and not my travel companion, she had to fly on a different airline. unacceptable

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Book cheap domestic flights from Chicago

Recent round-trip flight deals

8/9Sat
nonstopFrontier
2h 05mMDW-ATL
8/16Sat
nonstopFrontier
2h 05mATL-MDW
$76
5/27Tue
nonstopFrontier
2h 19mMDW-ATL
6/3Tue
nonstopFrontier
2h 06mATL-MDW
$77
5/14Wed
nonstopSouthwest
2h 05mMDW-LGA
5/28Wed
nonstopSouthwest
2h 20mLGA-MDW
$137
7/15Tue
nonstopSouthwest
2h 35mMDW-DEN
7/16Wed
nonstopSouthwest
2h 25mDEN-MDW
$151
8/20Wed
nonstopDelta
1h 54mMDW-ATL
8/27Wed
nonstopDelta
1h 56mATL-MDW
$159
6/21Sat
1 stopDelta
4h 07mMDW-EWR
6/24Tue
1 stopDelta
5h 54mEWR-MDW
$179
5/30Fri
1 stop
14h 01mMDW-EWR
6/6Fri
1 stop
22h 43mEWR-MDW
$196
5/30Fri
1 stopAllegiant Air
14h 01mMDW-EWR
6/6Fri
1 stopAllegiant Air
5h 08mEWR-MDW
$202
6/16Mon
1 stop
16h 25mMDW-LAS
6/20Fri
nonstop
3h 37mLAS-MDW
$202
6/2Mon
1 stopAllegiant Air
12h 01mMDW-EWR
6/5Thu
1 stopAllegiant Air
20h 27mEWR-MDW
$222

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Recent one-way flight deals

6/8Sun
nonstopFrontier
2h 09mMDW-ATL
$36
7/29Tue
nonstopFrontier
2h 06mMDW-ATL
$38
5/14Wed
nonstopSouthwest
2h 05mMDW-LGA
$69
6/10Tue
nonstopSouthwest
2h 35mMDW-DEN
$76
5/23Fri
nonstopDelta
2h 03mMDW-ATL
$81
10/11Sat
nonstopDelta
1h 59mMDW-ATL
$89
5/30Fri
1 stopAllegiant Air
14h 01mMDW-EWR
$95
6/2Mon
1 stopAllegiant Air
12h 01mMDW-EWR
$101
6/1Sun
1 stop
27h 48mMDW-PHX
$105
6/2Mon
2 stops
25h 31mMDW-ATL
$127

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Last minute flights from Midway to Worldwide

Last minute flight, train and bus deals

5/6Tue
nonstopFrontier
2h 08mMDW-ATL
5/15Thu
nonstopFrontier
2h 02mATL-MDW
$124
5/6Tue
nonstopFrontier
2h 08mMDW-ATL
5/12Mon
nonstopFrontier
2h 02mATL-MDW
$135
5/5Mon
nonstopFrontier
2h 04mMDW-ATL
5/15Thu
nonstopFrontier
2h 02mATL-MDW
$144
5/6Tue
nonstopFrontier
2h 08mMDW-ATL
5/27Tue
nonstopFrontier
2h 02mATL-MDW
$152
5/6Tue
nonstopSouthwest
2h 10mMDW-LGA
5/13Tue
nonstopSouthwest
2h 20mLGA-MDW
$210
5/6Tue
multi-stopSouthwest
4h 30mMDW-LGA
5/13Tue
nonstopSouthwest
2h 20mLGA-MDW
$220
5/6Tue
nonstopDelta
1h 57mMDW-ATL
1/17Sat
nonstopDelta
2h 01mATL-MDW
$237
5/6Tue
multi-stopDelta
4h 33mMDW-ATL
1/17Sat
nonstopDelta
2h 01mATL-MDW
$247
5/5Mon
multi-stop
29h 07mMDW-LAS
5/7Wed
multi-stop
26h 40mLAS-MDW
$597
5/5Mon
multi-stop
34h 14mMDW-LAS
5/7Wed
multi-stop
26h 40mLAS-MDW
$604

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Book cheap international flights from Midway

Recent round-trip flight deals

5/11Sun
nonstopSouthwest
3h 40mMDW-CUN
5/15Thu
nonstopSouthwest
3h 40mCUN-MDW
$247
5/19Mon
multi-stopSouthwest
8h 50mMDW-CUN
5/22Thu
nonstopSouthwest
3h 40mCUN-MDW
$299
6/10Tue
multi-stopAeromexico
7h 36mMDW-CUN
6/11Wed
multi-stopAeromexico
7h 45mCUN-MDW
$309
6/10Tue
multi-stopAeromexico
7h 36mMDW-CUN
6/11Wed
multi-stopAeromexico
10h 45mCUN-MDW
$316
6/6Fri
multi-stopDelta
11h 34mMDW-CUN
6/11Wed
multi-stopDelta
9h 10mCUN-MDW
$321
5/30Fri
multi-stopDelta
11h 42mMDW-CUN
6/4Wed
multi-stopDelta
10h 45mCUN-MDW
$325
6/3Tue
multi-stopFrontier
6h 20mMDW-CUN
6/8Sun
multi-stopFrontier
9h 31mCUN-MDW
$417
5/16Fri
multi-stopFrontier
18h 10mMDW-CUN
5/21Wed
multi-stopFrontier
28h 57mCUN-MDW
$427
8/1Fri
multi-stopKorean Air
35h 53mMDW-DEL
8/19Tue
multi-stopKorean Air
30h 36mDEL-MDW
$3,456
7/8Tue
multi-stopKorean Air
38h 18mMDW-DEL
8/10Sun
multi-stopKorean Air
28h 10mDEL-MDW
$3,932

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Recent one-way flight deals

6/23Mon
nonstopSouthwest
3h 35mMDW-CUN
$111
7/11Fri
nonstopSouthwest
3h 35mMDW-CUN
$121
6/10Tue
multi-stopAeromexico
9h 54mMDW-CUN
$139
6/26Thu
multi-stopAeromexico
9h 54mMDW-CUN
$144
7/1Tue
multi-stopDelta
5h 25mMDW-CUN
$146
5/30Fri
multi-stopFrontier
14h 46mMDW-CUN
$152
6/2Mon
multi-stopDelta
11h 04mMDW-CUN
$166
8/9Sat
multi-stopFrontier
25h 36mMDW-CUN
$168
7/30Wed
multi-stopVolaris
14h 18mMDW-CUN
$257
6/4Wed
multi-stopVolaris
14h 18mMDW-CUN
$271

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Everything you need to know for your flight from Midway

Information on your arrival and departure airports

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