$46 Find Deals on Flights from Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Worldwide departing on 10/14. 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.
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Find Cheap Flights from Chicago Midway Airport

Where can I fly from Chicago Midway Airport?Prices from MDW, departing Thu 10/16 and returning Thu 10/23

Book Cheap International Flights from Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip international flight deals from Midway to anywhere

Sat, Oct 25 - Tue, Oct 28
Multiple Airlines Logo
6:58 pm - 8:04 amORD-CUN
13h 06m1 stop
Multiple Airlines Logo
1:28 pm - 5:36 pmCUN-ORD
4h 08mnonstop
$233Multiple Airlines
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Sun, Oct 19 - Fri, Oct 24
Multiple Airlines Logo
6:30 am - 10:15 amORD-CUN
3h 45mnonstop
Multiple Airlines Logo
9:09 am - 6:46 pmCUN-ORD
9h 37m1 stop
$234Multiple Airlines
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Sun, Oct 5 - Thu, Oct 9
Spirit Airlines Logo
5:05 am - 12:44 pmORD-CUN
7h 39m1 stop
Spirit Airlines Logo
1:49 pm - 11:45 pmCUN-ORD
9h 56m1 stop
$235Spirit Airlines
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Wed, Dec 3 - Wed, Dec 10
Iberia Logo
4:45 pm - 7:55 amORD-MAD
8h 10mnonstop
Iberia Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$365Iberia
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Wed, Dec 3 - Wed, Dec 10
Iberia Logo
5:10 pm - 2:15 pmORD-MAD
14h 05m1 stop
Iberia Logo
11:35 am - 2:30 pmMAD-ORD
9h 55mnonstop
$368Iberia
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Wed, Dec 3 - Wed, Dec 10
Iberia Logo
5:10 pm - 12:40 pmORD-MAD
12h 30m1 stop
Iberia Logo
11:00 am - 5:36 pmMAD-ORD
13h 36m1 stop
$373Iberia
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Tue, Nov 18 - Wed, Nov 26
United Airlines Logo
1:36 pm - 9:00 amORD-BCN
12h 24m1 stop
United Airlines Logo
3:05 pm - 6:10 pmBCN-ORD
10h 05mnonstop
$482United Airlines
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Sat, Nov 22 - Mon, Dec 1
United Airlines Logo
9:10 pm - 8:20 amORD-BCN
28h 10m1 stop
United Airlines Logo
1:45 pm - 1:10 pmBCN-ORD
30h 25m1 stop
$483United Airlines
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Wed, Oct 15 - Thu, Oct 30
SWISS Logo
7:05 pm - 11:35 pmORD-BCN
21h 30m1 stop
SWISS Logo
6:45 am - 5:20 pmBCN-ORD
16h 35m1 stop
$484SWISS
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Wed, Oct 29 - Wed, Nov 5
Multiple Airlines Logo
7:50 pm - 12:50 pmORD-LCY
12h 00m1 stop
Multiple Airlines Logo
9:25 am - 7:30 pmLCY-ORD
16h 05m2 stops
$530Multiple Airlines
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Book Cheap Domestic Flights from Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip domestic flight deals from Midway

Sat, Sep 27 - Sat, Oct 4
Frontier Logo
6:15 am - 9:22 amMDW-ATL
2h 07mnonstop
Frontier Logo
10:46 pm - 11:41 pmATL-MDW
1h 55mnonstop
$83Frontier
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Sat, Oct 4 - Mon, Oct 6
Frontier Logo
6:15 am - 9:22 amMDW-ATL
2h 07mnonstop
Frontier Logo
10:46 pm - 11:41 pmATL-MDW
1h 55mnonstop
$84Frontier
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Fri, Oct 31 - Fri, Nov 7
Frontier Logo
1:37 pm - 4:35 pmMDW-ATL
1h 58mnonstop
Frontier Logo
9:05 pm - 10:08 pmATL-MDW
2h 03mnonstop
$85Frontier
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Sat, Oct 4 - Sat, Oct 11
Frontier Logo
11:21 am - 3:04 pmMDW-MCO
2h 43mnonstop
Frontier Logo
1:16 pm - 3:11 pmMCO-MDW
2h 55mnonstop
$99Frontier
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Fri, Oct 17 - Mon, Oct 20
Frontier Logo
5:10 am - 7:45 amMDW-DFW
2h 35mnonstop
Frontier Logo
9:01 pm - 11:20 pmDFW-MDW
2h 19mnonstop
$100Frontier
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Mon, Sep 29 - Thu, Oct 9
Multiple Airlines Logo
7:03 pm - 8:48 pmMDW-LAS
3h 45mnonstop
Multiple Airlines Logo
8:05 pm - 12:24 amLAS-MDW
26h 19m1 stop
$135Multiple Airlines
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Tue, Nov 18 - Wed, Nov 19
Southwest Logo
2:45 pm - 5:45 pmMDW-LGA
2h 00mnonstop
Southwest Logo
9:55 pm - 11:20 pmLGA-MDW
2h 25mnonstop
$137Southwest
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Sat, Oct 11 - Sat, Oct 18
Southwest Logo
7:45 pm - 10:20 pmMDW-HOU
2h 35mnonstop
Southwest Logo
5:55 pm - 8:20 pmHOU-MDW
2h 25mnonstop
$157Southwest
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Sat, Oct 25 - Sat, Nov 1
Southwest Logo
8:25 am - 12:30 pmMDW-HOU
4h 05m1 stop
Southwest Logo
8:10 pm - 10:30 pmHOU-MDW
2h 20mnonstop
$163Southwest
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Sat, Oct 11 - Sat, Oct 18
Southwest Logo
7:45 pm - 10:20 pmMDW-HOU
2h 35mnonstop
Southwest Logo
12:50 pm - 7:05 pmHOU-MDW
6h 15m1 stop
$167Southwest
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Booking Insights

KAYAK's insights & trends for flights from Midway

Get data-powered insights and trends into flights from Midway to help you find the cheapest flights, the best time to fly and much more.

Which are the most popular places to fly to from Chicago Midway Airport?

The domestic destinations KAYAK users have most searched for when searching for flights from Chicago Midway Airport.
Based on KAYAK flight searches, the most popular place to fly from Midway is New York (12% of total searches). The next most popular destinations are Dallas (8%) and Las Vegas Harry Reid Intl (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 Toronto, Tokyo and Bangkok.

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 round-trip price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most popular country to fly to from Chicago Midway Airport is Mexico (69% of total searches). The next most popular destinations are Canada (30%) and Dominican Republic (1%).

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 Jacksonville, Los Angeles, Charlotte, St. Louis and Salt Lake City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Jacksonville at $214, while the most expensive was St. Louis, at $302.

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 Guadalajara, Morelia, León, Cancún and Toronto. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Toronto at $195, while the most expensive was Cancún, at $393.

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 4h 50m. The next longest is Los Angeles at 4h 40m, followed by a flight to Oakland at 4h 40m.

What are the cheapest places to fly to from Chicago Midway Airport?

The cheapest destination for a flight from Chicago found on KAYAK in the last two weeks was Orlando and cost $37. The next cheapest destinations were Grand Rapids at $38 and Minneapolis at $38.

Good to know

Low seasonAugust
Cheapest flight$46
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from Chicago Midway Airport to Atlanta

FAQs for booking flights out of Chicago Midway Airport

  • Are there any airlines that operate flights from Chicago Midway International Airport (MDW) and are known for being environmentally friendly?

    If being environmentally friendly is one of your priorities, you may want to fly with Delta. Delta has a goal to replace 10% of its standard aviation fuel with sustainable aviation fuel by the end of 2030.

  • How can I go from downtown Chicago to Chicago Midway International Airport (MDW)?

    To go from downtown Chicago to Chicago Midway International Airport (MDW), you can always choose to drive, which normally takes around 20 minutes in total. Public transportation is a convenient option as well, like bus line 55, which will bring you to the airport in around 10 to 15 minutes depending on how traffic is at the time.

  • Are there any airlines that have lounges for passengers at Chicago Midway International Airport (MDW)?

    There are no airlines that currently have lounges at Chicago Midway International Airport (MDW). However, the airport does have a USO Midway Lounge, which is reserved for past and present members of the military, as well as their family members. In this lounge, travelers will have access to free snacks and drinks, as well as shower facilities.

  • What services does Chicago Midway International Airport (MDW) offer for travelers with limited mobility or disabilities?

    Chicago Midway International Airport (MDW) has wheelchairs that all guests are able to use for free. The airport also has accessible restroom stalls, elevators, and ramps that can be used to go to different floors and terminals. If you will need additional help navigating the airport, make sure to contact your airline in advance.

  • What is Midway also known as?

    Chicago Midway Airport’s airport code is MDW. It can also be referred to as Chicago Midway, Chicago Midway Intl, Midway, Midway Intl.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to your destination with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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 $109 one-way - $146 round-trip; Baltimore $89 one-way - $111 round-trip; Orlando $78 one-way - $133 round-trip
  • 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.

Reviews of the top 5 airlines serving from Midway to Worldwide

 
Need help choosing which airline to fly with from Midway to Worldwide? 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
SouthwestOverall score based on 4242 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

10.0 ExcellentG, Sep 2025LAS - ATL
Read more Southwest reviews

I wish they had movie screens in the headrests. The seats are much improved, more legroom and recently renovated. Bathroom was clean. Staff was outstanding!!

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

After being assaulted by a flight attendant I was then brushed off as oh well because he long braids didn’t mean to whip me in the eye. I have filed complaints and will see. But like any other issue I’ve had with kayak involved it’s been trash. Last time I’ll be using your app

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

Southwest's seats are the least comfortable I have ever sat in.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Southwest like most American domestic airlines, is a mediocre airline. But it is among the cheapest. Oh well.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

In Mexico charges too much for my luggage and I ask for help and nothing one lady she just disappeared 😡😡😡😡😡never going to fly there

Confusion over extra fees. Held up on ramp during boarding. Thin seat cushion. Minimal leg room.

The check-in is either at a kiosk that didn’t allow me to check-in because my middle name was not on the reservation or at an agent that cost $15.

Better communication about delayed flight. I am thankful for a small credit for late flight.

Liked on time, rear entry and exit from plane Dislike the use of duct tape to repair seat rests

Terrible. And they charged over $400 just for luggage. And threatened that I would loose my flight if I didn’t pay. So I didn’t have another choice but to pay.

They check you everything before entering to waiting room, if you have any liquid they take it away even if you buy it inside the airport, no recommend volaris, for mi know Alaska airline is better

They don’t give anything for free you have to pay for everything which it’s expected but at least give out water and a snack as a courtesy for flying with them.

The worst. Kayak sent notification at 2am and 10am regarding the delay. Then sends a notification an hour before original depart time that it will depart on time. I had to wait 8 hours at the airport. My family had to pay for lodging in Guadalajara where I was landing for pick up.

Seats were new and comfortable. Staff was fine. Missed my connection due to weather -which wasn’t their fault- but got no help at all. Gate staff sent me to customer service, which was and stayed unstaffed. Sign with QR code directed me to call or chat. Chat was useless. Call was returned after an hour. No itinerary offered by Frontier could get me home in less than 30 hours. Rebooked with another airline and got a partial refund that came to about 10 percent of what I paid to get home.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

The experience was good. No frills but I got there safe and sound and on time.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

sluggish boarding and arrival procedures, fake nice flight attendants, and lots of delays.

Disaster. They lied every step of the way. We ended up being delayed due to crew and then allegedly abandoned the flight because of a curfew at LGA. No rebooking to LGA at any reasonable time. No hotel. No meal vouchers. Had to sleep in the airport and fly to Newark instead. Will never fly Frontier again.

What I expected, nickeled and dined and a frontier flight attendant loudly complained about her job and lack of communication as she headed to the gate on her cell phone. Not professional.

As every law enforcement agency I could imagine surrounded the plane and we didn’t disembark for 2 hours and then had to stick around for another hour to go get our personal belongings after leaving them behind and being bused away from the plane, it was scary and inconvenient. We were given no information as to why this was happening. Lack of communication with passengers was disappointing.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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