$48 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 4/6. 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, 0 bags

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Find Cheap Flights from Chicago Midway Airport

Where can I fly from Chicago Midway Airport?Prices from MDW, departing Fri 5/1 and returning Fri 5/8

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

Tue, May 5 - Sat, May 9
Multiple Airlines Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Multiple Airlines Logo
3:22 pm - 7:55 am
CUN
-
ORD
16h 33m
1 stop
$243Multiple Airlines
Sat, Apr 11 - Tue, Apr 14
Spirit Airlines Logo
6:05 am - 9:51 am
ORD
-
CUN
3h 46mnonstop
Spirit Airlines Logo
11:06 am - 3:06 pm
CUN
-
ORD
4h 00mnonstop
$244Spirit Airlines
Sat, Apr 11 - Thu, Apr 16
Spirit Airlines Logo
6:05 am - 9:51 am
ORD
-
CUN
3h 46mnonstop
Spirit Airlines Logo
1:43 pm - 12:24 am
CUN
-
ORD
10h 41m
1 stop
$245Spirit Airlines
Sun, Apr 12 - Wed, Apr 22
TAP AIR PORTUGAL Logo
6:00 pm - 12:40 pm
ORD
-
MAD
11h 40m
1 stop
TAP AIR PORTUGAL Logo
7:40 am - 4:00 pm
MAD
-
ORD
15h 20m
1 stop
$512TAP AIR PORTUGAL
Tue, Apr 28 - Tue, May 5
Turkish Airlines Logo
8:10 pm - 11:15 pm
ORD
-
BCN
20h 05m
1 stop
Turkish Airlines Logo
12:10 pm - 9:40 am
BCN
-
ORD
28h 30m
1 stop
$516Turkish Airlines
Sun, Apr 12 - Thu, May 7
TAP AIR PORTUGAL Logo
6:00 pm - 9:25 pm
ORD
-
MAD
20h 25m
1 stop
TAP AIR PORTUGAL Logo
10:25 pm - 4:00 pm
MAD
-
ORD
24h 35m
1 stop
$519TAP AIR PORTUGAL
Mon, Apr 27 - Wed, May 6
Turkish Airlines Logo
8:10 pm - 10:45 am
ORD
-
BCN
31h 35m
1 stop
Turkish Airlines Logo
7:40 am - 9:40 am
BCN
-
ORD
33h 00m
1 stop
$522Turkish Airlines
Sun, Apr 12 - Wed, Apr 29
Turkish Airlines Logo
8:10 pm - 11:15 pm
ORD
-
BCN
20h 05m
1 stop
Turkish Airlines Logo
12:10 pm - 9:40 am
BCN
-
ORD
28h 30m
1 stop
$525Turkish Airlines
Sun, Apr 19 - Sun, Apr 26
TAP AIR PORTUGAL Logo
6:00 pm - 5:20 pm
ORD
-
MAD
16h 20m
1 stop
TAP AIR PORTUGAL Logo
6:35 am - 4:00 pm
MAD
-
ORD
16h 25m
1 stop
$530TAP AIR PORTUGAL
Sun, Apr 12 - Tue, Apr 21
Multiple Airlines Logo
11:25 am - 2:40 pm
ORD
-
BVA
20h 15m
2 stops
Multiple Airlines Logo
10:55 am - 9:40 am
BVA
-
ORD
29h 45m
2 stops
$646Multiple Airlines

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

Sun, Apr 19 - Wed, Apr 22
Frontier Logo
6:00 am - 9:15 am
MDW
-
ATL
2h 15mnonstop
Frontier Logo
6:26 pm - 7:31 pm
ATL
-
MDW
2h 05mnonstop
$83Frontier
Tue, May 5 - Sat, May 9
Frontier Logo
6:00 am - 9:09 am
MDW
-
ATL
2h 09mnonstop
Frontier Logo
10:00 am - 11:04 am
ATL
-
MDW
2h 04mnonstop
$84Frontier
Thu, Apr 23 - Sat, Apr 25
Frontier Logo
2:15 pm - 5:21 pm
MDW
-
ATL
2h 06mnonstop
Frontier Logo
5:34 pm - 6:37 pm
ATL
-
MDW
2h 03mnonstop
$86Frontier
Mon, Apr 13 - Wed, Apr 22
Frontier Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Frontier Logo
11:10 am - 7:31 pm
MIA
-
MDW
9h 21m
1 stop
$101Frontier
Mon, Apr 13 - Wed, Apr 22
Multiple Airlines Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Multiple Airlines Logo
3:54 pm - 10:14 pm
MIA
-
MDW
7h 20m
1 stop
$106Multiple Airlines
Wed, May 27 - Fri, May 29
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$108Frontier
Tue, Apr 21 - Sat, Apr 25
Frontier Logo
2:15 pm - 1:16 am
MDW
-
EWR
10h 01m
1 stop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$108Frontier
Tue, May 12 - Thu, May 21
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$109Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
10:29 pm - 7:31 pm
EWR
-
MDW
22h 02m
1 stop
$110Frontier
Tue, Apr 21 - Wed, Apr 22
Multiple Airlines Logo
2:15 pm - 9:03 pm
MDW
-
FLL
5h 48m
1 stop
Multiple Airlines Logo
1:58 pm - 7:31 pm
FLL
-
MDW
6h 33m
1 stop
$137Multiple Airlines
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 (10% of total searches). The next most popular destinations are Dallas (8%) and Las Vegas Harry Reid Intl (8%).

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 London, Rome and Cancún.

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 (74% of total searches). The next most popular destinations are Canada (22%) and Dominican Republic (2%).

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, Salt Lake City and Charleston. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Charleston at $239, while the most expensive was Los Angeles, at $310.

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 Guadalajara at $222, while the most expensive was Cancún, at $379.

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 00m. The next longest is Oakland at 4h 35m, followed by a flight to San Francisco at 4h 35m.

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 New York and cost $28. The next cheapest destinations were Dallas at $44 and Miami at $44.

Good to know

Low seasonJanuary
Cheapest flight$47
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to Miami

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 $160 one-way - $181 round-trip; Orlando $130 one-way - $224 round-trip; Phoenix $137 one-way - $273 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 4337 reviews
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
8.0Comfort
Airline reviews

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

6.0 GoodAnthony & Kathy, Mar 2026
PHX - TUL
Read more Southwest reviews

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

During the flight, the only refreshments provided were crackers and soft drinks; no substantial food was offered despite the international route. Furthermore, our initial flight was delayed, causing us to miss the connecting flight in Atlanta. The airline did not hold the connection, and we were informed that the next available flight is not for another 24 hours. While I am aware of alternative options via JetBlue, they operate out of JFK, which is not a viable solution for us as a resident of New Jersey.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

It was cold on the flight. The crew was very pleasant. I didn't order any food. We were delayed due to Captain waiting on maintenance log. He kept us informed though. The flight itself was smooth. I would definitely fly with Allegiant again!

I had a fantastic experience with Allegiant. I had wheelchair assistance and they helped me find my luggage and brought me to my car. Even loaded my luggage. Wonderful service!! Thank you Allegiant!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

The flights were on time, the ground crew and on board crews were kind and efficient. The free snacks for Premium+ were good, similar to US First Class snacks. The plane were clean and bright! Complaints? The seats were worn and the seat-back pockets were missing. Overall, I'll book again with Volaris. Ignore the negative social media posts, understand what your fare includes, buy the add ons you need. We had no problems with our personal items and carryons.

Overall a good red eye. Crew chatted very loudly the whole time making it difficult to sleep.

It’s a 2 1/2 hour flight so good and comfort was not my real concern. Safety, easy, fast was what I was looking for. The crews were great, plane was clean, boarding from CBX was fantastic! Definitely traveling this way again.

The money you save flying volaris is not worth it

Is was a good short flight with some turbulence! I would fly Volaris again.

We had boarding passes for the next flight but we could not catch the flight in the small airport just because volaris closed the boarding at the counters an hour before for which we had to sepnd almost 3+ hours to catch next flight. There are hardly anyone who can speak english, but thank God, we have found an young man who could not only speak English but helped us book for the next flight. The air crafts are noisy and scary sometimes to hear that squeeking noises during the take off and during the flight. They do not even offer a cup of coffee for free in flight. The prices are super high and the services are zero. That’s pretty much for this airlines in summary.

Unfortunately it was not a good flight got canceled had to be at the airport all night long to get a different flight to another airport my first flight with Volaris was very bad. Poor services

The boarding , and it would be nice if they would let us know head of time about flight changes

The fly was 2 hours delayed and the plane was old and dirty. A very umcorfotable flight, which I won't recomend to anyone

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.

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Everything you need to know for your flight from Midway

Information on your arrival and departure airports