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Find deals on flights from Chicago Midway Airport 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 Anywhere departing on 6/26. 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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Where can I fly from Chicago Midway Airport?

Prices from MDW, departing Tue 7/2 and returning Tue 7/9

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 (20% of total searches). The next most popular destinations are Seattle/Tacoma Intl (8%) 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, 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 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 (89% of total searches). The next most popular destinations are Mexico (7%) and Canada (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 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 $79, while the most expensive was Detroit, at $295.

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 Cancún at $115, while the most expensive was Zacatecas, at $287.

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, California 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

March

Cheapest flight

$48
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago Midway Airport to Orlando 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 $72 one-way - $138 round-trip; Denver $49 one-way - $88 round-trip; Orlando $77 one-way - $151 round-trip
  • Morning departure is around 12% 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 10410 reviews
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
8.6Crew
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 domestic flights from Chicago

Recent round-trip flight deals

6/13Thu
nonstopFrontier
1h 59mMDW-ATL
6/15Sat
nonstopFrontier
1h 59mATL-MDW
$56
6/12Wed
nonstopFrontier
2h 01mMDW-ATL
6/19Wed
nonstopFrontier
2h 00mATL-MDW
$57
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
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
6/15Sat
1 stopVolaris
27h 15mMDW-JFK
6/16Sun
1 stopVolaris
11h 21mJFK-MDW
$953
7/1Mon
1 stopVolaris
27h 15mMDW-JFK
7/7Sun
1 stopVolaris
11h 21mJFK-MDW
$1,084

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Recent one-way flight deals

6/26Wed
nonstopFrontier
2h 01mMDW-ATL
$44
6/22Sat
nonstopFrontier
2h 01mMDW-ATL
$45
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
11/28Thu
2 stopsVolaris
17h 43mMDW-LAS
$453
11/6Wed
2 stopsVolaris
17h 38mMDW-LAS
$485

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Last minute flights from Midway to Anywhere

Last minute flight, train and bus deals

6/7Fri
nonstopFrontier
2h 01mMDW-ATL
6/11Tue
nonstopFrontier
2h 00mATL-MDW
$119
6/7Fri
nonstopFrontier
2h 01mMDW-ATL
6/8Sat
nonstopFrontier
1h 59mATL-MDW
$122
6/7Fri
nonstopFrontier
2h 01mMDW-ATL
6/15Sat
nonstopFrontier
1h 59mATL-MDW
$124
6/6Thu
multi-stopDelta
7h 24mMDW-JFK
6/11Tue
multi-stopDelta
7h 51mJFK-MDW
$306
6/4Tue
multi-stopDelta
7h 13mMDW-BOS
6/8Sat
multi-stopDelta
4h 28mBOS-MDW
$334
6/3Mon
multi-stopAllegiant Air
5h 00mMDW-MCO
6/7Fri
multi-stopAllegiant Air
6h 57mMCO-MDW
$393
6/5Wed
multi-stopVolaris
12h 25mMDW-LAX
6/9Sun
multi-stopVolaris
12h 20mLAX-MDW
$796
6/5Wed
multi-stopPorter Airlines
19h 15mMDW-EWR
6/12Wed
multi-stopPorter Airlines
16h 42mEWR-MDW
$800
6/5Wed
multi-stopVolaris
12h 25mMDW-LAX
6/10Mon
multi-stopVolaris
13h 00mLAX-MDW
$809
6/6Thu
multi-stopPorter Airlines
5h 20mMDW-EWR
6/8Sat
multi-stopPorter Airlines
22h 07mEWR-MDW
$864

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Book cheap international flights from Midway

Recent round-trip flight deals

6/16Sun
multi-stopFrontier
25h 16mMDW-CUN
6/19Wed
multi-stopFrontier
6h 40mCUN-MDW
$331
6/18Tue
multi-stop
12h 44mMDW-CUN
6/27Thu
multi-stop
8h 20mCUN-MDW
$335
9/14Sat
multi-stopAeromexico
5h 48mMDW-CUN
9/19Thu
multi-stopAeromexico
6h 41mCUN-MDW
$389
9/25Wed
multi-stopDelta
11h 45mMDW-CUN
9/28Sat
multi-stopDelta
12h 04mCUN-MDW
$390
9/20Fri
multi-stopDelta
11h 45mMDW-CUN
9/24Tue
multi-stopDelta
13h 23mCUN-MDW
$401
10/19Sat
multi-stopAeromexico
9h 42mMDW-CUN
10/23Wed
multi-stopAeromexico
13h 29mCUN-MDW
$467
10/2Wed
multi-stopKLM
20h 35mMDW-DEL
10/29Tue
multi-stopKLM
24h 13mDEL-MDW
$1,213
9/14Sat
multi-stopKLM
21h 10mMDW-DEL
10/2Wed
multi-stopKLM
23h 38mDEL-MDW
$1,261
8/19Mon
multi-stopKorean Air
25h 41mMDW-MNL
9/22Sun
multi-stopKorean Air
26h 01mMNL-MDW
$1,433
8/20Tue
multi-stopKorean Air
25h 41mMDW-MNL
10/23Wed
multi-stopKorean Air
26h 01mMNL-MDW
$1,464

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Recent one-way flight deals

6/25Tue
multi-stopAeromexico
9h 14mMDW-CUN
$168
11/18Mon
multi-stopAeromexico
6h 48mMDW-CUN
$179
7/23Tue
multi-stopDelta
9h 27mMDW-CUN
$180
6/7Fri
multi-stopFrontier
20h 08mMDW-CUN
$181
7/4Thu
multi-stopFrontier
14h 21mMDW-CUN
$185
9/2Mon
multi-stopVolaris
14h 21mMDW-CUN
$260
7/16Tue
multi-stopDelta
10h 22mMDW-CUN
$282
10/21Mon
multi-stopVolaris
24h 43mMDW-CUN
$291
11/20Wed
multi-stopKLM
22h 15mMDW-DEL
$674
9/17Tue
multi-stopKLM
20h 40mMDW-DEL
$797

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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:

$639
$728
$477
$37