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$42 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 Anywhere departing on 8/8. 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
Sat 8/24
Sat 8/31

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Where can I fly from Chicago Midway Airport?

Prices from MDW, departing Sat 8/24 and returning Sat 8/31

Flights from Midway - Travel Insights & Trends

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 (18% of total searches). The next most popular destinations are Seattle/Tacoma Intl (6%) and Las Vegas Harry Reid Intl (5%).

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, Rome and Toronto.

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 price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most countries to fly to from Chicago Midway Airport is United States (86% of total searches). The next most popular destinations are Mexico (9%) and Canada (5%).

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 New York, Phoenix, Raleigh, Miami and Tampa. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Raleigh at $78, while the most expensive was Miami, at $144.

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 Zacatecas, Guadalajara, Morelia, León and Cancún. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was San Juan at $102, while the most expensive was Zacatecas, 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 5h 05m. The next longest is Oakland at 4h 45m, followed by a flight to San Juan Luis Munoz Marin Intl Airport at 4h 35m.

Good to know

Low season

January

High season

July

Cheapest flight

$42
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago Midway Airport to Dallas/Fort Worth Airport

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.

See more FAQs

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 $78 one-way - $147 round-trip; Denver $51 one-way - $86 round-trip; Tampa $50 one-way - $96 round-trip
  • Morning departure is around 14% more expensive than an evening flight, on average*.
  • 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.
See more tips
*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 Anywhere

Need help choosing which airline to fly with from Midway to Anywhere? 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
8.6Crew
7.4Food
7.9Comfort
8.0Entertainment
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 domestic flights from Chicago

Recent round-trip flight deals

8/20Tue
nonstopFrontier
2h 01mMDW-ATL
8/27Tue
nonstopFrontier
2h 05mATL-MDW
$47
8/13Tue
nonstopFrontier
2h 01mMDW-ATL
8/17Sat
nonstopFrontier
2h 06mATL-MDW
$48
9/21Sat
nonstopDelta
1h 55mMDW-ATL
9/23Mon
nonstopDelta
1h 53mATL-MDW
$119
9/24Tue
nonstopDelta
1h 54mMDW-ATL
9/25Wed
nonstopDelta
1h 53mATL-MDW
$132
8/19Mon
nonstopSouthwest
2h 20mMDW-BOS
8/22Thu
nonstopSouthwest
2h 40mBOS-MDW
$209
8/23Fri
nonstopSouthwest
2h 10mMDW-LGA
8/30Fri
nonstopSouthwest
2h 20mLGA-MDW
$213
8/21Wed
1 stopPorter Airlines
14h 00mMDW-EWR
8/28Wed
1 stopPorter Airlines
10h 27mEWR-MDW
$427
9/13Fri
1 stopPorter Airlines
7h 30mMDW-EWR
9/20Fri
1 stopPorter Airlines
14h 47mEWR-MDW
$434
8/26Mon
1 stopVolaris
27h 15mMDW-JFK
8/27Tue
1 stopVolaris
32h 17mJFK-MDW
$933
8/17Sat
1 stopVolaris
27h 15mMDW-JFK
8/20Tue
1 stopVolaris
32h 17mJFK-MDW
$959

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Recent one-way flight deals

8/8Thu
nonstopFrontier
2h 03mMDW-ATL
$43
9/25Wed
nonstopFrontier
2h 23mMDW-DFW
$44
8/22Thu
nonstopDelta
1h 58mMDW-ATL
$60
8/13Tue
1 stopDelta
4h 28mMDW-EWR
$78
8/9Fri
1 stopAllegiant Air
19h 51mMDW-EWR
$91
9/27Fri
1 stopAllegiant Air
13h 55mMDW-EWR
$102
9/15Sun
1 stopPorter Airlines
5h 50mMDW-EWR
$226
9/29Sun
1 stopPorter Airlines
8h 00mMDW-EWR
$227
8/12Mon
1 stopVolaris
12h 30mMDW-LAX
$302
9/3Tue
2 stopsVolaris
27h 59mMDW-LAX
$385

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Last minute flights from Midway to Anywhere

Last minute flight, train and bus deals

7/30Tue
nonstopFrontier
2h 00mMDW-ATL
8/17Sat
nonstopFrontier
2h 06mATL-MDW
$123
7/30Tue
nonstopFrontier
2h 00mMDW-ATL
8/15Thu
nonstopFrontier
2h 05mATL-MDW
$128
7/30Tue
multi-stopDelta
4h 58mMDW-EWR
8/6Tue
multi-stopDelta
3h 33mEWR-MDW
$278
7/29Mon
nonstopSouthwest
2h 05mMDW-LGA
8/1Thu
nonstopSouthwest
2h 25mLGA-MDW
$325
7/27Sat
multi-stopDelta
6h 05mMDW-EWR
8/3Sat
multi-stopDelta
3h 33mEWR-MDW
$326
7/29Mon
nonstopSouthwest
2h 05mMDW-LGA
8/1Thu
multi-stopSouthwest
11h 45mLGA-MDW
$335
7/28Sun
multi-stopPorter Airlines
14h 00mMDW-EWR
8/6Tue
multi-stopPorter Airlines
16h 42mEWR-MDW
$777
7/30Tue
multi-stopPorter Airlines
10h 05mMDW-EWR
8/3Sat
multi-stopPorter Airlines
9h 52mEWR-MDW
$784
7/30Tue
multi-stopVolaris
13h 30mMDW-LAX
8/7Wed
multi-stopVolaris
12h 20mLAX-MDW
$956
7/30Tue
multi-stopVolaris
13h 30mMDW-LAX
8/6Tue
multi-stopVolaris
12h 25mLAX-MDW
$967

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Book cheap international flights from Midway

Recent round-trip flight deals

10/16Wed
multi-stopFrontier
19h 51mMDW-CUN
10/21Mon
multi-stopFrontier
11h 51mCUN-MDW
$289
9/19Thu
multi-stop
17h 10mMDW-CUN
9/24Tue
multi-stop
9h 39mCUN-MDW
$294
9/9Mon
multi-stopAeromexico
9h 20mMDW-CUN
9/11Wed
multi-stopAeromexico
13h 23mCUN-MDW
$376
9/7Sat
multi-stopDelta
12h 40mMDW-CUN
9/13Fri
multi-stopDelta
12h 23mCUN-MDW
$386
9/21Sat
multi-stopDelta
10h 37mMDW-CUN
9/24Tue
multi-stopDelta
12h 23mCUN-MDW
$391
8/24Sat
multi-stopAeromexico
19h 32mMDW-CUN
8/30Fri
multi-stopAeromexico
13h 46mCUN-MDW
$439
1/18Sat
multi-stopVolaris
13h 18mMDW-CUN
1/21Tue
multi-stopVolaris
12h 59mCUN-MDW
$454
1/15Wed
multi-stopVolaris
11h 29mMDW-CUN
1/19Sun
multi-stopVolaris
12h 54mCUN-MDW
$469
9/23Mon
multi-stopKLM
21h 48mMDW-DEL
10/6Sun
multi-stopKLM
23h 38mDEL-MDW
$1,073
9/2Mon
multi-stopKLM
21h 40mMDW-DEL
9/15Sun
multi-stopKLM
23h 39mDEL-MDW
$1,079

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Recent one-way flight deals

8/24Sat
multi-stop
18h 50mMDW-CUN
$129
10/26Sat
multi-stopFrontier
10h 22mMDW-CUN
$132
7/30Tue
multi-stopAeromexico
5h 19mMDW-CUN
$168
8/27Tue
multi-stopAeromexico
13h 44mMDW-CUN
$177
10/21Mon
multi-stopVolaris
10h 47mMDW-CUN
$181
1/16Thu
multi-stopDelta
10h 26mMDW-CUN
$187
8/8Thu
multi-stopDelta
13h 44mMDW-CUN
$196
9/21Sat
multi-stopVolaris
10h 47mMDW-CUN
$241
9/23Mon
multi-stopKLM
21h 48mMDW-DEL
$571
9/3Tue
multi-stopKLM
21h 20mMDW-DEL
$577

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Flights from Chicago Midway Airport to Anywhere

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Anywhere - Chicago Midway Airport

Cabin classes:

$438
$606
$424
$39