$38 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 10/25. 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
1 adult, Economy

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Find Cheap Flights from Chicago Midway Airport

Where can I fly from Chicago Midway Airport?Prices from MDW, departing Sat 8/16 and returning Sat 8/23

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, Aug 16 - Sat, Aug 23
Spirit Airlines Logo
6:10 am - 9:39 amORD-CUN
3h 29mnonstop
Spirit Airlines Logo
10:34 am - 2:49 pmCUN-ORD
4h 15mnonstop
$210Spirit Airlines
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Sat, Aug 16 - Sat, Aug 23
 Logo
12:25 pm - 9:35 pmORD-CUN
9h 10m1 stop
 Logo
10:34 am - 2:49 pmCUN-ORD
4h 15mnonstop
Sun, Sep 28 - Sat, Oct 4
 Logo
12:25 pm - 8:55 pmORD-CUN
8h 30m1 stop
 Logo
10:45 am - 2:50 pmCUN-ORD
4h 05mnonstop
Sun, Sep 21 - Fri, Oct 3
TAP AIR PORTUGAL Logo
6:00 pm - 12:40 pmORD-MAD
11h 40m1 stop
TAP AIR PORTUGAL Logo
7:40 am - 4:30 pmMAD-ORD
15h 50m1 stop
$288TAP AIR PORTUGAL
Find Deal
Wed, Nov 12 - Fri, Nov 21
TAP AIR PORTUGAL Logo
7:10 pm - 11:30 pmORD-MAD
21h 20m1 stop
TAP AIR PORTUGAL Logo
7:40 am - 3:15 pmMAD-ORD
14h 35m1 stop
$292TAP AIR PORTUGAL
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Wed, Nov 12 - Fri, Nov 21
TAP AIR PORTUGAL Logo
7:10 pm - 11:30 pmORD-MAD
21h 20m1 stop
TAP AIR PORTUGAL Logo
7:30 am - 3:15 pmMAD-ORD
14h 45m1 stop
$293TAP AIR PORTUGAL
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Sun, Nov 2 - Tue, Nov 18
TAP AIR PORTUGAL Logo
8:20 pm - 11:45 pmORD-BCN
20h 25m1 stop
TAP AIR PORTUGAL Logo
9:10 pm - 3:00 pmBCN-ORD
24h 50m1 stop
$353TAP AIR PORTUGAL
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Wed, Nov 19 - Tue, Nov 25
TAP AIR PORTUGAL Logo
7:10 pm - 1:45 pmORD-BCN
11h 35m1 stop
TAP AIR PORTUGAL Logo
6:05 pm - 3:00 pmBCN-ORD
27h 55m1 stop
$357TAP AIR PORTUGAL
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Fri, Nov 7 - Fri, Nov 14
TAP AIR PORTUGAL Logo
8:15 pm - 11:45 pmORD-BCN
20h 30m1 stop
TAP AIR PORTUGAL Logo
6:45 am - 3:15 pmBCN-ORD
15h 30m1 stop
$360TAP AIR PORTUGAL
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Wed, Aug 13 - Wed, Aug 27
Virgin Atlantic Logo
4:40 pm - 8:50 amORD-LCY
10h 10m1 stop
Virgin Atlantic Logo
9:20 am - 2:40 pmLCY-ORD
11h 20m1 stop
$542Virgin Atlantic
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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

Thu, Aug 14 - Sun, Aug 17
Frontier Logo
6:20 am - 9:28 amMDW-ATL
2h 08mnonstop
Frontier Logo
10:15 pm - 11:17 pmATL-MDW
2h 02mnonstop
$80Frontier
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Sun, Aug 17 - Tue, Aug 19
Frontier Logo
6:20 am - 9:28 amMDW-ATL
2h 08mnonstop
Frontier Logo
8:00 am - 9:02 amATL-MDW
2h 02mnonstop
$90Frontier
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Wed, Aug 13 - Sun, Aug 17
Frontier Logo
11:39 am - 2:45 pmMDW-ATL
2h 06mnonstop
Frontier Logo
10:15 pm - 11:17 pmATL-MDW
2h 02mnonstop
$91Frontier
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Wed, Aug 13 - Sat, Aug 16
Frontier Logo
6:02 pm - 8:39 pmMDW-DFW
2h 37mnonstop
Frontier Logo
11:27 am - 1:50 pmDFW-MDW
2h 23mnonstop
$100Frontier
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Tue, Sep 2 - Tue, Sep 2
Southwest Logo
6:00 am - 9:00 amMDW-LGA
2h 00mnonstop
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
$137Southwest
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Thu, Sep 4 - Sun, Sep 7
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
7:30 am - 9:35 amMIA-MDW
3h 05mnonstop
$137Southwest
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Mon, Sep 22 - Fri, Sep 26
 Logo
4:48 pm - 8:21 pmMDW-LAS
5h 33m1 stop
 Logo
3:22 pm - 8:52 pmLAS-MDW
3h 30mnonstop
Mon, Sep 29 - Thu, Oct 2
 Logo
7:03 pm - 8:48 pmMDW-LAS
3h 45mnonstop
 Logo
12:37 pm - 9:58 pmLAS-MDW
7h 21m1 stop
Sat, Sep 6 - Sat, Sep 13
Delta Logo
6:17 pm - 11:30 pmMDW-EWR
4h 13m1 stop
Delta Logo
8:15 am - 3:26 pmEWR-MDW
8h 11m1 stop
$167Delta
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Wed, Sep 3 - Wed, Sep 10
Delta Logo
6:00 am - 2:24 pmMDW-EWR
7h 24m1 stop
Delta Logo
12:27 pm - 5:37 pmEWR-MDW
6h 10m1 stop
$172Delta
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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 (20% of total searches). The next most popular destinations are Seattle/Tacoma Intl (7%) and Dallas (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 Bangkok, London and Toronto.

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 (65% of total searches). The next most popular destinations are Canada (29%) and Dominican Republic (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 Jacksonville, Los Angeles, El Paso, Charlotte and Charleston. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Jacksonville at $198, while the most expensive was El Paso, at $331.

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 $112, while the most expensive was Durango, at $349.

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 Oakland at 4h 40m, followed by a flight to San Francisco at 4h 40m.

Good to know

Low seasonJune
High seasonDecember
Cheapest flight$38
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly with an average 21% increase in price.
Flight from Chicago Midway Airport to Dallas/Fort Worth 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 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 $110 one-way - $167 round-trip; Denver $101 one-way - $169 round-trip; Orlando $110 one-way - $159 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 4241 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.6Entertainment
Airline reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

4.0 OkayBobby, Jul 2025BNA - MDW
Read more Southwest reviews

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

this crew didn't care much. bumping carts into seats more times than i care to remember

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

Everything was fine except the entertainment was not working for half of the flight.

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!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

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.

The flight was delayed an hour and a half, and they would not update the board on when the flight was supposed to take off. Once the plane arrived, they started the boarding process before the plane was even ready for the passengers so we had to wait another 45 minutes on the tarmac while we waited for the plane to be ready for us. In my opinion, there is no point in starting the boarding process when you are not ready to board the plane. This just causes a crowded gate with everyone from zone one and zone two standing up going nowhere.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

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