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Find deals on flights from Chicago Midway Airport from $49

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Anywhere departing on 5/7. 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 5/26
Sun 6/2

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Where can I fly from Chicago Midway Airport?

Prices from MDW, departing Sun 5/26 and returning Sun 6/2

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 (17% of total searches). The next most popular destinations are Seattle/Tacoma Intl (7%) and Atlanta Hartsfield-Jackson (7%).

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 (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 Phoenix, Raleigh, Miami, Tampa and Detroit. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Raleigh at $50, while the most expensive was Phoenix, at $147.

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 $243.

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 San Francisco at 4h 39m.

Good to know

Low season

January

High season

March

Cheapest flight

$49
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago Midway Airport to Las Vegas

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 $76 one-way - $127 round-trip; Denver $66 one-way - $89 round-trip; Dallas $55 one-way - $98 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 10966 reviews
7.4food
8.0entertainment
8.6crew
7.9comfort
8.2boarding
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

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!

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

Is an airline for poor people there for, you can expect bad service, bad attitude from its employees

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.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

If you don’t check in 24 hours in advance, they will charge you $110 to check your bag instead of the $30. I did not get an email with this information and did not check in. In addition, my flight home was cancelled at layover and I had to spend the night in the airport, and then have another layover at another airport before making it home. Will not fly frontier again.

Book cheap domestic flights from Chicago

Recent round-trip flight deals

5/7Tue
nonstopFrontier
2h 05mMDW-ATL
5/8Wed
nonstopFrontier
1h 58mATL-MDW
$47
6/1Sat
nonstopFrontier
2h 38mMDW-DFW
6/5Wed
nonstopFrontier
2h 18mDFW-MDW
$48
6/11Tue
1 stopDelta
4h 16mMDW-EWR
6/12Wed
1 stopDelta
4h 51mEWR-MDW
$178
6/1Sat
1 stopDelta
4h 37mMDW-EWR
6/4Tue
1 stopDelta
4h 04mEWR-MDW
$183
5/4Sat
3 stops
20h 57mMDW-LAX
5/6Mon
1 stop
12h 06mLAX-MDW
$222
5/6Mon
nonstopSouthwest
2h 05mMDW-LGA
5/9Thu
1 stopSouthwest
11h 50mLGA-MDW
$271
5/4Sat
3 stops
20h 57mMDW-LAX
5/6Mon
2 stops
36h 08mLAX-MDW
$273
5/28Tue
nonstopSouthwest
4h 25mMDW-LAX
5/29Wed
nonstopSouthwest
4h 00mLAX-MDW
$330
5/23Thu
1 stopPorter Airlines
9h 40mMDW-EWR
5/30Thu
1 stopPorter Airlines
5h 07mEWR-MDW
$479
5/22Wed
1 stopPorter Airlines
10h 05mMDW-EWR
5/29Wed
2 stopsPorter Airlines
16h 42mEWR-MDW
$484

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Recent one-way flight deals

6/23Sun
nonstopFrontier
2h 36mMDW-DFW
$49
5/15Wed
nonstopFrontier
4h 04mMDW-LAS
$49
7/29Mon
nonstopFrontier
1h 56mMDW-ATL
$49
5/25Sat
1 stopDelta
5h 15mMDW-DFW
$88
6/1Sat
1 stopDelta
5h 37mMDW-EWR
$94
5/30Thu
2 stopsSpirit Airlines
9h 04mMDW-EWR
$203
5/22Wed
1 stopPorter Airlines
7h 30mMDW-EWR
$241
6/6Thu
1 stopPorter Airlines
6h 30mMDW-EWR
$242
5/4Sat
1 stopVolaris
12h 30mMDW-LAX
$327
5/26Sun
1 stopVolaris
12h 30mMDW-LAX
$361

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Last minute flights from Midway to Anywhere

Last minute flight, train and bus deals

5/1Wed
nonstopFrontier
2h 45mMDW-DFW
5/7Tue
nonstopFrontier
2h 21mDFW-MDW
$87
5/1Wed
nonstopFrontier
2h 45mMDW-DFW
5/19Sun
nonstopFrontier
2h 25mDFW-MDW
$89
5/1Wed
multi-stopFrontier
7h 22mMDW-DFW
5/8Wed
nonstopFrontier
2h 22mDFW-MDW
$91
4/27Sat
multi-stopDelta
6h 03mMDW-ATL
4/30Tue
multi-stopDelta
5h 40mATL-MDW
$290
4/30Tue
nonstopSouthwest
1h 50mMDW-ATL
5/2Thu
multi-stopSouthwest
4h 25mATL-MDW
$303
4/30Tue
multi-stopSouthwest
3h 15mMDW-ATL
5/2Thu
multi-stopSouthwest
4h 25mATL-MDW
$307
4/29Mon
multi-stopDelta
5h 07mMDW-DFW
5/1Wed
multi-stopDelta
7h 05mDFW-MDW
$334
5/1Wed
multi-stopPorter Airlines
5h 20mMDW-EWR
5/9Thu
multi-stopPorter Airlines
6h 12mEWR-MDW
$725
5/1Wed
multi-stopPorter Airlines
7h 30mMDW-EWR
5/3Fri
multi-stopPorter Airlines
8h 22mEWR-MDW
$774
4/27Sat
multi-stopVolaris
19h 27mMDW-LAX
4/28Sun
multi-stopVolaris
12h 15mLAX-MDW
$1,335

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Book cheap international flights from Midway

Recent round-trip flight deals

5/16Thu
multi-stopFrontier
13h 54mMDW-CUN
5/22Wed
multi-stopFrontier
8h 44mCUN-MDW
$322
5/10Fri
multi-stopFrontier
10h 21mMDW-CUN
5/17Fri
multi-stopFrontier
8h 53mCUN-MDW
$323
4/29Mon
multi-stopDelta
6h 51mMDW-CUN
5/8Wed
multi-stopDelta
13h 51mCUN-MDW
$390
5/17Fri
multi-stopDelta
15h 09mMDW-CUN
5/24Fri
multi-stopDelta
9h 28mCUN-MDW
$416
5/17Fri
multi-stopKLM
21h 38mMDW-DEL
5/25Sat
multi-stopKLM
22h 48mDEL-MDW
$1,396
5/5Sun
multi-stopKLM
21h 40mMDW-DEL
5/25Sat
multi-stopKLM
22h 48mDEL-MDW
$1,443
7/13Sat
multi-stopVirgin Atlantic
31h 15mMDW-DEL
7/26Fri
multi-stopVirgin Atlantic
26h 51mDEL-MDW
$1,505
6/1Sat
multi-stopVirgin Atlantic
27h 53mMDW-DEL
6/29Sat
multi-stopVirgin Atlantic
41h 40mDEL-MDW
$1,574
5/30Thu
multi-stopAir France
22h 44mMDW-DEL
6/12Wed
multi-stopAir France
26h 59mDEL-MDW
$1,714
7/13Sat
multi-stopAir France
40h 59mMDW-DEL
8/14Wed
multi-stopAir France
26h 58mDEL-MDW
$1,720

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Recent one-way flight deals

6/2Sun
multi-stopFrontier
10h 33mMDW-CUN
$171
5/10Fri
multi-stopFrontier
25h 58mMDW-CUN
$173
5/3Fri
multi-stopAeromexico
7h 38mMDW-CUN
$176
5/15Wed
multi-stopAeromexico
18h 28mMDW-CUN
$190
7/2Tue
multi-stopDelta
12h 40mMDW-CUN
$229
6/3Mon
multi-stopDelta
10h 19mMDW-CUN
$237
6/29Sat
multi-stopVolaris
14h 18mMDW-CUN
$468
5/17Fri
multi-stopKLM
21h 38mMDW-DEL
$679
5/21Tue
multi-stopKLM
21h 38mMDW-DEL
$681
5/28Tue
multi-stopVolaris
12h 19mMDW-CUN
$724

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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:

$599
$505
$291
$32