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Find deals on flights from Chicago Midway Airport from $50

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 9/2. 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
sáb. 6/29
sáb. 7/6

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Where can I fly from Chicago Midway Airport?

Prices from MDW, departing sáb. 6/29 and returning sáb. 7/6

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 (24% of total searches). The next most popular destinations are Seattle/Tacoma Intl (8%) and Los Angeles (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 Toronto, Paris 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

$50
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 4% 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 10457 reviews
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

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.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

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

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

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

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.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

6/12mié.
nonstopFrontier
2h 01mMDW-ATL
6/13jue.
nonstopFrontier
1h 55mATL-MDW
$51
6/12mié.
nonstopFrontier
2h 01mMDW-ATL
6/18mar.
nonstopFrontier
2h 00mATL-MDW
$53
9/21sáb.
1 stopDelta
4h 09mMDW-EWR
9/25mié.
1 stopDelta
6h 44mEWR-MDW
$156
10/2mié.
1 stopDelta
5h 06mMDW-EWR
10/5sáb.
1 stopDelta
7h 10mEWR-MDW
$172
6/21vie.
1 stopAllegiant Air
4h 30mMDW-MCO
6/24lun.
1 stopAllegiant Air
7h 31mMCO-MDW
$232
7/12vie.
1 stopAllegiant Air
4h 30mMDW-MCO
7/15lun.
1 stopAllegiant Air
7h 02mMCO-MDW
$239
6/13jue.
1 stopPorter Airlines
6h 30mMDW-EWR
6/18mar.
1 stopPorter Airlines
6h 12mEWR-MDW
$471
6/13jue.
1 stopPorter Airlines
6h 30mMDW-EWR
6/26mié.
2 stopsPorter Airlines
8h 27mEWR-MDW
$477
6/14vie.
1 stopVolaris
27h 15mMDW-JFK
6/15sáb.
1 stopVolaris
32h 17mJFK-MDW
$871
6/15sáb.
1 stopVolaris
27h 15mMDW-JFK
6/17lun.
1 stopVolaris
32h 22mJFK-MDW
$920

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Recent one-way flight deals

9/2lun.
nonstopFrontier
1h 56mMDW-ATL
$40
9/2lun.
nonstopFrontier
1h 56mMDW-ATL
$41
9/9lun.
1 stopDelta
5h 14mMDW-EWR
$78
6/19mié.
nonstopDelta
1h 59mMDW-ATL
$85
7/1lun.
1 stopAllegiant Air
11h 57mMDW-EWR
$103
7/1lun.
1 stopAllegiant Air
4h 30mMDW-MCO
$105
6/13jue.
1 stopPorter Airlines
6h 30mMDW-EWR
$239
6/30dom.
2 stopsPorter Airlines
10h 10mMDW-EWR
$244
6/10lun.
1 stopVolaris
12h 30mMDW-LAX
$367
6/12mié.
1 stopVolaris
12h 25mMDW-LAX
$368

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Last minute flights from Midway to Anywhere

Last minute flight, train and bus deals

6/4mar.
nonstopFrontier
2h 03mMDW-ATL
6/12mié.
nonstopFrontier
2h 00mATL-MDW
$72
6/2dom.
nonstopFrontier
2h 05mMDW-ATL
6/6jue.
nonstopFrontier
1h 55mATL-MDW
$99
6/4mar.
multi-stopDelta
5h 02mMDW-MCO
6/8sáb.
multi-stopDelta
5h 53mMCO-MDW
$262
6/3lun.
multi-stopAllegiant Air
5h 00mMDW-MCO
6/10lun.
multi-stopAllegiant Air
6h 57mMCO-MDW
$271
6/4mar.
multi-stopDelta
9h 01mMDW-LAS
6/4mar.
multi-stopDelta
6h 02mLAS-MDW
$274
6/3lun.
multi-stopAllegiant Air
5h 00mMDW-MCO
6/10lun.
multi-stopAllegiant Air
6h 57mMCO-MDW
$276
6/2dom.
multi-stopVolaris
12h 30mMDW-LAX
6/7vie.
multi-stopVolaris
12h 20mLAX-MDW
$664
6/4mar.
multi-stopPorter Airlines
5h 20mMDW-EWR
6/4mar.
multi-stopPorter Airlines
16h 42mEWR-MDW
$703
6/3lun.
multi-stopPorter Airlines
14h 00mMDW-EWR
6/4mar.
multi-stopPorter Airlines
6h 12mEWR-MDW
$764
6/2dom.
multi-stopVolaris
12h 30mMDW-LAX
6/11mar.
multi-stopVolaris
13h 05mLAX-MDW
$824

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Book cheap international flights from Midway

Recent round-trip flight deals

6/8sáb.
multi-stopFrontier
25h 51mMDW-CUN
6/12mié.
multi-stopFrontier
20h 14mCUN-MDW
$316
7/1lun.
multi-stopFrontier
7h 15mMDW-CUN
7/4jue.
multi-stopFrontier
22h 28mCUN-MDW
$317
8/24sáb.
multi-stopDelta
9h 27mMDW-CUN
8/29jue.
multi-stopDelta
13h 46mCUN-MDW
$390
8/26lun.
multi-stopDelta
8h 07mMDW-CUN
8/31sáb.
multi-stopDelta
9h 04mCUN-MDW
$394
9/24mar.
multi-stopKLM
20h 35mMDW-DEL
10/6dom.
multi-stopKLM
23h 38mDEL-MDW
$1,250
9/5jue.
multi-stopKLM
21h 20mMDW-DEL
9/25mié.
multi-stopKLM
23h 38mDEL-MDW
$1,262
8/25dom.
multi-stopAir France
25h 49mMDW-DEL
9/6vie.
multi-stopAir France
28h 33mDEL-MDW
$1,283
7/8lun.
multi-stopAir France
46h 41mMDW-DEL
7/21dom.
multi-stopAir France
52h 34mDEL-MDW
$1,315
8/21mié.
multi-stopKorean Air
25h 26mMDW-MNL
9/22dom.
multi-stopKorean Air
24h 21mMNL-MDW
$1,430
8/19lun.
multi-stopKorean Air
25h 26mMDW-MNL
9/22dom.
multi-stopKorean Air
26h 01mMNL-MDW
$1,433

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Recent one-way flight deals

6/4mar.
multi-stop
20h 09mMDW-CUN
$147
6/12mié.
multi-stop
22h 28mMDW-CUN
$148
6/14vie.
multi-stopFrontier
7h 15mMDW-CUN
$150
6/6jue.
multi-stopFrontier
13h 29mMDW-CUN
$151
6/5mié.
multi-stopDelta
10h 19mMDW-CUN
$180
7/5vie.
multi-stopAeromexico
13h 55mMDW-CUN
$191
6/5mié.
multi-stopDelta
10h 19mMDW-CUN
$192
8/15jue.
multi-stopAeromexico
19h 15mMDW-CUN
$224
9/2lun.
multi-stopVolaris
14h 21mMDW-CUN
$324
8/27mar.
multi-stopVolaris
14h 38mMDW-CUN
$389

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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