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Find deals on flights from Chicago Midway Airport from $55

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 6/30. 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
Sun 6/9
Sun 6/16

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Where can I fly from Chicago Midway Airport?

Prices from MDW, departing Sun 6/9 and returning Sun 6/16

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 Chicago Midway is New York (26% of total searches). The next most popular destinations are Seattle/Tacoma Intl (6%) and Los Angeles (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, San Juan 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 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 (88% of total searches). The next most popular destinations are Mexico (7%) and Canada (4%).

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 $55, while the most expensive was Detroit, at $192.

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 $238.

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 10m. The next longest is Oakland, California at 4h 45m, followed by a flight to Long Beach at 4h 35m.

Good to know

Low season

January

High season

March

Cheapest flight

$55
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago Midway Airport to New York LaGuardia 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 Chicago 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 $71 one-way - $126 round-trip; Denver $49 one-way - $88 round-trip; Dallas $55 one-way - $98 round-trip
  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
  • 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 10768 reviews
7.9Comfort
8.0Entertainment
8.6Crew
7.4Food
8.2Boarding
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

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.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

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?

The flight was early arriving. I love that when I go to collect my luggage, that there is no wait time luggage is on spinner waiting for me. There was no food served nor any entertainment. Seats are a little snug, front to back. But a quick flight.

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.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

5/21Tue
nonstopFrontier
2h 05mMDW-ATL
6/11Tue
nonstopFrontier
2h 00mATL-MDW
$53
6/8Sat
nonstopFrontier
2h 01mMDW-ATL
6/11Tue
nonstopFrontier
2h 01mATL-MDW
$55
6/15Sat
nonstopDelta
1h 59mMDW-ATL
6/15Sat
nonstopDelta
1h 56mATL-MDW
$157
6/1Sat
nonstopDelta
1h 56mMDW-ATL
6/3Mon
nonstopDelta
1h 50mATL-MDW
$177
6/6Thu
nonstopSouthwest
2h 05mMDW-LGA
6/7Fri
nonstopSouthwest
2h 20mLGA-MDW
$223
5/31Fri
1 stopAllegiant Air
19h 43mMDW-EWR
6/7Fri
1 stopAllegiant Air
9h 49mEWR-MDW
$235
5/31Fri
1 stopAllegiant Air
19h 43mMDW-EWR
6/3Mon
1 stopAllegiant Air
9h 48mEWR-MDW
$246
5/17Fri
nonstopSouthwest
2h 10mMDW-LGA
5/22Wed
1 stopSouthwest
7h 05mLGA-MDW
$266
5/28Tue
1 stopPorter Airlines
9h 40mMDW-EWR
5/30Thu
1 stopPorter Airlines
10h 27mEWR-MDW
$449
6/1Sat
1 stopPorter Airlines
6h 30mMDW-EWR
6/4Tue
1 stopPorter Airlines
6h 12mEWR-MDW
$453

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Recent one-way flight deals

6/30Sun
nonstopFrontier
2h 00mMDW-ATL
$46
6/1Sat
1 stopFrontier
6h 16mMDW-FLL
$47
6/15Sat
nonstopDelta
1h 52mMDW-ATL
$79
7/4Thu
1 stopDelta
4h 16mMDW-EWR
$94
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$108
6/14Fri
1 stopAllegiant Air
10h 57mMDW-EWR
$111
5/26Sun
1 stopPorter Airlines
5h 50mMDW-EWR
$231
5/26Sun
1 stopPorter Airlines
5h 50mMDW-EWR
$232
6/10Mon
1 stopVolaris
12h 30mMDW-LAX
$331
5/20Mon
1 stopVolaris
12h 30mMDW-LAX
$364

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Last minute flights from Midway to Anywhere

Last minute flight, train and bus deals

5/15Wed
nonstopFrontier
2h 05mMDW-ATL
5/21Tue
nonstopFrontier
1h 57mATL-MDW
$103
5/14Tue
nonstopFrontier
2h 02mMDW-ATL
5/30Thu
nonstopFrontier
2h 01mATL-MDW
$108
5/14Tue
nonstopFrontier
2h 05mMDW-ATL
5/21Tue
nonstopFrontier
1h 57mATL-MDW
$113
5/15Wed
nonstopDelta
1h 55mMDW-ATL
5/22Wed
multi-stopDelta
4h 35mATL-MDW
$232
5/15Wed
nonstopDelta
1h 56mMDW-ATL
5/15Wed
multi-stopDelta
4h 51mATL-MDW
$233
5/12Sun
multi-stopAllegiant Air
16h 20mMDW-HOU
5/16Thu
multi-stopAllegiant Air
20h 24mHOU-MDW
$556
5/14Tue
multi-stopPorter Airlines
5h 20mMDW-EWR
5/23Thu
multi-stopPorter Airlines
8h 27mEWR-MDW
$763
5/15Wed
multi-stopPorter Airlines
9h 12mMDW-BOS
5/23Thu
multi-stopPorter Airlines
12h 52mBOS-MDW
$765
5/12Sun
multi-stopVolaris
12h 30mMDW-LAX
5/21Tue
multi-stopVolaris
19h 20mLAX-MDW
$784
5/14Tue
multi-stopVolaris
12h 30mMDW-LAX
5/24Fri
multi-stopVolaris
12h 20mLAX-MDW
$818

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Book cheap international flights from Midway

Recent round-trip flight deals

6/4Tue
multi-stopFrontier
9h 06mMDW-CUN
6/12Wed
multi-stopFrontier
6h 40mCUN-MDW
$271
5/29Wed
multi-stopFrontier
8h 12mMDW-CUN
6/11Tue
multi-stopFrontier
9h 21mCUN-MDW
$272
9/17Tue
multi-stopDelta
12h 43mMDW-CUN
9/24Tue
multi-stopDelta
13h 52mCUN-MDW
$390
9/13Fri
multi-stopDelta
9h 42mMDW-CUN
9/16Mon
multi-stopDelta
12h 44mCUN-MDW
$400
9/6Fri
multi-stopAeromexico
20h 17mMDW-CUN
9/9Mon
multi-stopAeromexico
13h 29mCUN-MDW
$444
7/19Fri
multi-stopAeromexico
13h 31mMDW-CUN
7/24Wed
multi-stopAeromexico
6h 59mCUN-MDW
$477
9/11Wed
multi-stopKLM
20h 35mMDW-DEL
10/23Wed
multi-stopKLM
23h 38mDEL-MDW
$1,003
8/20Tue
multi-stopKLM
20h 35mMDW-DEL
9/4Wed
multi-stopKLM
23h 38mDEL-MDW
$1,100
9/14Sat
multi-stopAir France
26h 30mMDW-DEL
10/11Fri
multi-stopAir France
27h 11mDEL-MDW
$1,135
5/28Tue
multi-stopAir France
22h 44mMDW-DEL
6/3Mon
multi-stopAir France
31h 56mDEL-MDW
$1,246

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Recent one-way flight deals

5/16Thu
multi-stopFrontier
8h 31mMDW-CUN
$123
5/29Wed
multi-stopFrontier
8h 12mMDW-CUN
$124
5/15Wed
multi-stopAeromexico
12h 51mMDW-CUN
$180
5/15Wed
multi-stopAeromexico
19h 33mMDW-CUN
$185
7/23Tue
multi-stopDelta
10h 20mMDW-CUN
$289
6/2Sun
multi-stopVolaris
15h 55mMDW-CUN
$312
5/30Thu
multi-stopDelta
10h 19mMDW-CUN
$320
6/27Thu
multi-stopVolaris
15h 55mMDW-CUN
$338
9/5Thu
multi-stopKLM
22h 00mMDW-DEL
$570
9/15Sun
multi-stopKLM
21h 26mMDW-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:

$524
$611
$292
$27