$53 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Find Cheap Flights from Chicago Midway Airport

Where can I fly from Chicago Midway Airport?Prices from MDW, departing Wed 7/16 and returning Wed 7/23

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

Mon, Jul 7 - Fri, Jul 11
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$201Spirit Airlines
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Mon, Jul 7 - Fri, Jul 11
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$202Spirit Airlines
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Mon, Jul 7 - Sat, Jul 12
Spirit Airlines Logo
6:00 am - 9:50 amORD-CUN
3h 50mnonstop
Spirit Airlines Logo
10:55 am - 2:49 pmCUN-ORD
3h 54mnonstop
$208Spirit Airlines
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Sun, Oct 5 - Thu, Oct 16
TAP AIR PORTUGAL Logo
6:00 pm - 7:20 pmORD-BCN
18h 20m1 stop
TAP AIR PORTUGAL Logo
6:00 am - 12:35 pmBCN-ORD
13h 35m1 stop
$386TAP AIR PORTUGAL
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Sat, Sep 6 - Fri, Sep 19
TAP AIR PORTUGAL Logo
6:15 pm - 7:25 pmORD-BCN
18h 10m1 stop
TAP AIR PORTUGAL Logo
6:00 am - 4:30 pmBCN-ORD
17h 30m1 stop
$388TAP AIR PORTUGAL
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Sun, Sep 7 - Sat, Sep 13
TAP AIR PORTUGAL Logo
6:00 pm - 2:10 pmORD-BCN
13h 10m1 stop
TAP AIR PORTUGAL Logo
6:00 am - 4:30 pmBCN-ORD
17h 30m1 stop
$389TAP AIR PORTUGAL
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Mon, Sep 1 - Mon, Sep 8
 Logo
10:40 am - 9:55 pmORD-BVA
28h 15m2 stops
 Logo
9:35 pm - 8:11 pmBVA-ORD
29h 36m2 stops
Wed, Aug 13 - Wed, Aug 20
 Logo
7:25 pm - 10:10 pmORD-BVA
19h 45m2 stops
 Logo
10:20 am - 6:15 pmBVA-ORD
14h 55m2 stops
Sun, Aug 10 - Tue, Aug 19
 Logo
10:40 am - 9:10 pmORD-BVA
27h 30m2 stops
 Logo
10:20 pm - 8:16 pmBVA-ORD
28h 56m2 stops
Mon, Sep 15 - Mon, Oct 20
Turkish Airlines Logo
11:45 pm - 4:40 amORD-DEL
18h 25m1 stop
Turkish Airlines Logo
6:20 am - 10:00 pmDEL-ORD
26h 10m1 stop
$651Turkish 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

Tue, Aug 19 - Tue, Aug 26
Southwest Logo
9:05 pm - 11:35 pmMDW-SEA
4h 30mnonstop
Southwest Logo
5:35 am - 11:30 amSEA-MDW
3h 55mnonstop
$109Southwest
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Sat, Sep 13 - Tue, Sep 16
Southwest Logo
5:25 pm - 7:55 pmMDW-SEA
4h 30mnonstop
Southwest Logo
5:35 am - 11:30 amSEA-MDW
3h 55mnonstop
$117Southwest
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Fri, Sep 12 - Sun, Sep 21
Frontier Logo
8:34 am - 12:15 pmMDW-MCO
2h 41mnonstop
Frontier Logo
5:45 am - 7:39 amMCO-MDW
2h 54mnonstop
$126Frontier
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Mon, Sep 15 - Sun, Sep 21
Frontier Logo
8:34 am - 12:15 pmMDW-MCO
2h 41mnonstop
Frontier Logo
5:45 am - 7:39 amMCO-MDW
2h 54mnonstop
$127Frontier
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Sat, Sep 13 - Tue, Sep 16
Southwest Logo
5:25 pm - 7:55 pmMDW-SEA
4h 30mnonstop
Southwest Logo
10:45 pm - 9:00 amSEA-MDW
8h 15m1 stop
$127Southwest
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Fri, Oct 3 - Fri, Oct 10
Frontier Logo
8:34 am - 12:15 pmMDW-MCO
2h 41mnonstop
Frontier Logo
5:50 am - 7:44 amMCO-MDW
2h 54mnonstop
$136Frontier
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Thu, Aug 21 - Mon, Aug 25
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
$137Southwest
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Wed, Sep 3 - Tue, Sep 9
Southwest Logo
5:55 pm - 9:10 pmMDW-LGA
2h 15mnonstop
Southwest Logo
6:00 am - 7:20 amLGA-MDW
2h 20mnonstop
$140Southwest
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Tue, Jul 1 - Tue, Jul 8
Southwest Logo
7:20 pm - 10:30 pmMDW-LGA
2h 10mnonstop
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
$141Southwest
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Tue, Jul 1 - Fri, Jul 4
Southwest Logo
7:20 pm - 10:30 pmMDW-LGA
2h 10mnonstop
Southwest Logo
6:00 pm - 7:25 pmLGA-MDW
2h 25mnonstop
$142Southwest
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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 (17% of total searches). The next most popular destinations are Houston (5%) and Dallas (5%).

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, Paris 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 (61% of total searches). The next most popular destinations are Canada (20%) and Dominican Republic (15%).

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 Salt Lake City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Provo at $111, while the most expensive was Salt Lake City, at $275.

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 $154, while the most expensive was León, at $370.

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 seasonAugust
High seasonDecember
Cheapest flight$53
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from Chicago Midway Airport to New York LaGuardia 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 $120 one-way - $175 round-trip; Denver $100 one-way - $176 round-trip; Orlando $88 one-way - $232 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.

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 4278 reviews
7.6Entertainment
8.0Comfort
7.1Food
8.2Boarding
8.6Crew
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Overall, aside from the baggage issue, it was as good as one expects.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I want to single out flight attendant Mitch who was in the Premium Economy section. When my wife’s hearing aide dropped through the cushion under the seat he was able to locate it and return it to her. Food was a different matter. Dinner was fine. Breakfast was another matter. They had a yogurt dish that the ran out of and the alternative was not very good according to those we talked to.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

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.

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.

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.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Everything you need to know for your flight from Midway

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