$44 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 1/19. 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 dl. 1/26 and returning dl. 2/2

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

ds., gen. 31 - dt., febr. 3
Spirit Airlines Logo
6:05 am - 10:54 am
ORD
-
CUN
3h 49mnonstop
Spirit Airlines Logo
11:59 am - 2:53 pm
CUN
-
ORD
3h 54mnonstop
$214Spirit Airlines
dj., gen. 22 - dj., gen. 29
Frontier Logo
7:11 am - 12:19 pm
ORD
-
CUN
4h 08mnonstop
Frontier Logo
11:40 am - 2:49 pm
CUN
-
ORD
4h 09mnonstop
$215Frontier
dt., gen. 20 - dv., gen. 23
Spirit Airlines Logo
5:15 am - 12:16 pm
ORD
-
CUN
6h 01m1 stop
Spirit Airlines Logo
11:59 am - 2:53 pm
CUN
-
ORD
3h 54mnonstop
$216Spirit Airlines
dg., gen. 18 - dc., gen. 28
TAP AIR PORTUGAL Logo
8:25 pm - 8:20 pm
ORD
-
BCN
16h 55m1 stop
TAP AIR PORTUGAL Logo
6:45 am - 3:00 pm
BCN
-
ORD
15h 15m1 stop
$409TAP AIR PORTUGAL
dc., febr. 11 - dt., febr. 17
TAP AIR PORTUGAL Logo
7:10 pm - 8:20 pm
ORD
-
BCN
18h 10m1 stop
TAP AIR PORTUGAL Logo
10:55 am - 3:00 pm
BCN
-
ORD
35h 05m1 stop
$416TAP AIR PORTUGAL
dg., gen. 11 - dv., gen. 16
Icelandair Logo
6:30 pm - 1:15 pm
ORD
-
BCN
11h 45m1 stop
Icelandair Logo
11:50 am - 5:20 pm
BCN
-
ORD
12h 30m1 stop
$419Icelandair
dg., abr. 19 - dv., maig 15
TAP AIR PORTUGAL Logo
6:00 pm - 12:40 pm
ORD
-
MAD
11h 40m1 stop
TAP AIR PORTUGAL Logo
7:40 am - 4:00 pm
MAD
-
ORD
15h 20m1 stop
$472TAP AIR PORTUGAL
dc., febr. 25 - dt., març 3
Lufthansa Logo
6:00 pm - 11:35 pm
ORD
-
MAD
22h 35m1 stop
Lufthansa Logo
6:00 am - 6:40 pm
MAD
-
ORD
19h 40m2 stops
$473Lufthansa
dg., gen. 11 - dt., gen. 20
Multiple Airlines Logo
10:10 am - 5:45 am
ORD
-
MAD
12h 35m1 stop
Multiple Airlines Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
$474Multiple Airlines
dl., gen. 12 - dl., gen. 26
Multiple Airlines Logo
6:30 pm - 8:40 pm
ORD
-
BVA
19h 10m2 stops
Multiple Airlines Logo
9:10 am - 5:20 pm
BVA
-
ORD
15h 10m2 stops
$537Multiple 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

dv., gen. 9 - dj., gen. 15
Frontier Logo
3:01 pm - 7:11 pm
MDW
-
MIA
3h 10mnonstop
Frontier Logo
4:44 pm - 7:09 pm
MIA
-
MDW
3h 25mnonstop
$88Frontier
ds., febr. 14 - ds., febr. 21
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
1:00 pm - 3:19 pm
DFW
-
MDW
2h 19mnonstop
$90Frontier
dj., gen. 15 - dl., gen. 19
Frontier Logo
11:05 am - 1:48 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
1:00 pm - 3:19 pm
DFW
-
MDW
2h 19mnonstop
$91Frontier
dv., gen. 23 - dv., gen. 30
Frontier Logo
1:00 pm - 4:49 pm
MDW
-
MCO
2h 49mnonstop
Frontier Logo
5:49 pm - 7:52 pm
MCO
-
MDW
3h 03mnonstop
$92Frontier
dt., febr. 24 - dj., febr. 26
Frontier Logo
6:10 am - 5:49 pm
MDW
-
MIA
10h 39m1 stop
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
$93Frontier
ds., febr. 14 - ds., febr. 21
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
10:44 am - 9:33 pm
DFW
-
MDW
10h 49m1 stop
$93Frontier
ds., gen. 24 - dg., gen. 25
Southwest Logo
5:35 pm - 8:40 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:30 pm - 8:15 pm
LGA
-
MDW
2h 45mnonstop
$97Southwest
dj., gen. 22 - dj., gen. 29
Southwest Logo
8:25 am - 11:35 am
MDW
-
LGA
2h 10mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$117Southwest
dl., febr. 23 - dc., febr. 25
Southwest Logo
8:00 pm - 11:00 pm
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$118Southwest
dg., gen. 18 - dj., gen. 22
Multiple Airlines Logo
11:05 am - 7:56 pm
MDW
-
FLL
7h 51m1 stop
Multiple Airlines Logo
10:49 pm - 7:52 pm
FLL
-
MDW
22h 03m1 stop
$142Multiple 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 (18% of total searches). The next most popular destinations are Miami (7%) and Fort Lauderdale (6%).

What are the most popular international flights out of Chicago Midway Airport?

The international destinations KAYAK users have most searched for when searching for flights from Chicago Midway Airport.

There are many international destinations you can fly to from Chicago Midway Airport. The most popular international destinations among KAYAK users are London, Tokyo and Punta Cana.

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 (77% of total searches). The next most popular destinations are Canada (20%) and Jamaica (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, San Diego, Los Angeles, Detroit and San Antonio. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Detroit at $238, while the most expensive was San Antonio, at $389.

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 Zacatecas. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Morelia at $177, while the most expensive was Aguascalientes, at $458.

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 San Francisco at 4h 40m, followed by a flight to San Juan Luis Munoz Marin Intl Airport 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 Miami and cost $29. The next cheapest destinations were New York at $33 and Atlanta at $34.

Good to know

Low seasonAugust
Cheapest flight$44
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 17% lower on average.
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 $113 one-way - $140 round-trip; Orlando $108 one-way - $188 round-trip; Phoenix $123 one-way - $190 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 4256 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

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.

WE were delayed about an hour and never any communications from the employees working the gate. We also were moved to a total of three gates.

I love how they show love to their customers and care about them too.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

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.

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.

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.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Everything you need to know for your flight from Midway

Information on your arrival and departure airports