$41 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 11/28. 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 Wed 12/17 and returning Wed 12/24

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, Jan 13 - Thu, Feb 19
Spirit Airlines Logo
5:15 am - 12:16 pmORD-CUN
6h 01m1 stop
Spirit Airlines Logo
12:06 pm - 3:07 pmCUN-ORD
4h 01mnonstop
$223Spirit Airlines
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Tue, Feb 17 - Fri, Feb 20
Multiple Airlines Logo
6:05 am - 11:01 amORD-CUN
3h 56mnonstop
Multiple Airlines Logo
11:38 am - 2:41 pmCUN-ORD
4h 03mnonstop
$224Multiple Airlines
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Sun, Dec 14 - Thu, Dec 18
Frontier Logo
11:43 am - 4:52 pmORD-CUN
4h 09mnonstop
Frontier Logo
6:22 pm - 9:32 pmCUN-ORD
4h 10mnonstop
$225Frontier
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Sun, Jan 25 - Wed, Jan 28
Multiple Airlines Logo
11:55 am - 1:20 pmORD-BCN
18h 25m1 stop
Multiple Airlines Logo
6:35 pm - 9:12 amBCN-ORD
21h 37m1 stop
$439Multiple Airlines
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Sat, Jan 17 - Sun, Jan 25
Multiple Airlines Logo
12:00 pm - 1:20 pmORD-BCN
18h 20m1 stop
Multiple Airlines Logo
6:35 pm - 6:29 pmBCN-ORD
30h 54m1 stop
$442Multiple Airlines
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Sun, Apr 12 - Tue, Apr 21
TAP AIR PORTUGAL Logo
6:00 pm - 7:20 pmORD-BCN
18h 20m1 stop
TAP AIR PORTUGAL Logo
5:45 pm - 4:00 pmBCN-ORD
29h 15m1 stop
$443TAP AIR PORTUGAL
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Wed, Dec 31 - Thu, Jan 8
Iberia Logo
6:30 pm - 2:50 pmORD-MAD
13h 20m1 stop
Iberia Logo
9:35 pm - 8:15 pmMAD-ORD
29h 40m2 stops
$449Iberia
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Sun, Mar 8 - Wed, Mar 18
Iberia Logo
6:40 pm - 8:50 amORD-MAD
8h 10mnonstop
Iberia Logo
1:15 pm - 8:07 pmMAD-ORD
12h 52m1 stop
$450Iberia
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Mon, Mar 16 - Tue, Mar 24
Multiple Airlines Logo
12:50 pm - 7:00 amORD-MAD
12h 10m1 stop
Multiple Airlines Logo
6:25 am - 8:10 pmMAD-ORD
19h 45m2 stops
$451Multiple Airlines
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Mon, Jan 12 - Thu, Jan 22
Multiple Airlines Logo
9:00 pm - 8:40 pmORD-BVA
16h 40m1 stop
Multiple Airlines Logo
9:55 am - 7:15 pmBVA-ORD
16h 20m1 stop
$489Multiple 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

Thu, Dec 25 - Thu, Jan 1
Frontier Logo
6:12 am - 9:30 amMDW-ATL
2h 18mnonstop
Frontier Logo
9:10 pm - 10:12 pmATL-MDW
2h 02mnonstop
$77Frontier
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Tue, Dec 2 - Sat, Dec 6
Frontier Logo
2:49 pm - 5:53 pmMDW-ATL
2h 04mnonstop
Frontier Logo
1:02 pm - 1:59 pmATL-MDW
1h 57mnonstop
$78Frontier
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Fri, Dec 12 - Sun, Dec 14
Frontier Logo
8:42 pm - 11:48 pmMDW-ATL
2h 06mnonstop
Frontier Logo
5:11 pm - 6:12 pmATL-MDW
2h 01mnonstop
$79Frontier
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Fri, Dec 19 - Wed, Dec 24
Frontier Logo
8:00 am - 10:42 amMDW-DFW
2h 42mnonstop
Frontier Logo
7:00 am - 9:21 amDFW-MDW
2h 21mnonstop
$90Frontier
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Sun, Dec 7 - Mon, Dec 8
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
Frontier Logo
9:02 am - 11:20 amDFW-MDW
2h 18mnonstop
$91Frontier
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Sun, Dec 7 - Sun, Dec 14
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
Frontier Logo
6:05 am - 6:12 pmDFW-MDW
12h 07m1 stop
$94Frontier
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Tue, Feb 3 - Fri, Feb 6
Frontier Logo
2:15 pm - 12:06 amMDW-MCO
8h 51m1 stop
Frontier Logo
5:49 pm - 7:52 pmMCO-MDW
3h 03mnonstop
$97Frontier
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Mon, Jan 19 - Sun, Jan 25
Frontier Logo
9:43 am - 1:28 pmMDW-MCO
2h 45mnonstop
Frontier Logo
3:15 pm - 10:19 pmMCO-MDW
8h 04m1 stop
$98Frontier
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Fri, Jan 9 - Wed, Jan 21
Multiple Airlines Logo
2:47 pm - 7:15 pmMDW-MIA
3h 28mnonstop
Multiple Airlines Logo
7:00 am - 12:05 pmMIA-MDW
6h 05m1 stop
$116Multiple Airlines
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Mon, Dec 15 - Wed, Dec 24
Southwest Logo
8:20 pm - 10:15 pmMDW-LAS
3h 55mnonstop
Southwest Logo
2:05 pm - 7:35 pmLAS-MDW
3h 30mnonstop
$131Southwest
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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 (9% of total searches). The next most popular destinations are Orlando (8%) 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 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 (86% of total searches). The next most popular destinations are Canada (13%) 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, 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 $194, while the most expensive was El Paso, at $444.

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, Toronto and Durango. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Toronto at $199, while the most expensive was León, at $270.

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 Jose 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 $29 and Houston at $29.

Good to know

Low seasonAugust
Cheapest flight$43
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Chicago Midway Airport to Orlando

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 $99 one-way - $155 round-trip; Denver $110 one-way - $149 round-trip; Orlando $89 one-way - $189 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 4245 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

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

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

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.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

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.

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 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.

I got to where I needed to go quickly. There were no amenities. And the seats were painful.

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.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

Everything you need to know for your flight from Midway

Information on your arrival and departure airports