$116 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 8/19. 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 Fri 7/31 and returning Fri 8/7

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

Sun, Aug 23 - Thu, Aug 27
Volaris Logo
6:21 am - 3:28 pm
ORD
-
CUN
9h 07m
1 stop
Volaris Logo
9:50 pm - 5:52 am
CUN
-
ORD
8h 02m
1 stop
$308Volaris
Fri, Oct 9 - Mon, Oct 12
Volaris Logo
7:35 am - 9:03 pm
ORD
-
CUN
13h 28m
1 stop
Volaris Logo
11:16 am - 12:06 am
CUN
-
ORD
12h 50m
1 stop
$309Volaris
Wed, Jul 15 - Mon, Jul 20
Volaris Logo
2:53 am - 12:04 pm
ORD
-
CUN
9h 11m
1 stop
Volaris Logo
9:50 pm - 5:52 am
CUN
-
ORD
8h 02m
1 stop
$310Volaris
Sun, Aug 23 - Tue, Nov 17
TAP AIR PORTUGAL Logo
6:00 pm - 5:20 pm
ORD
-
MAD
16h 20m
1 stop
TAP AIR PORTUGAL Logo
6:00 pm - 3:30 pm
MAD
-
ORD
28h 30m
1 stop
$554TAP AIR PORTUGAL
Wed, Nov 18 - Mon, Nov 23
Scandinavian Airlines Logo
7:15 pm - 4:10 pm
ORD
-
MAD
13h 55m
1 stop
Scandinavian Airlines Logo
5:00 pm - 4:45 pm
MAD
-
ORD
30h 45m
1 stop
$563Scandinavian Airlines
Wed, Nov 11 - Tue, Nov 24
Scandinavian Airlines Logo
7:15 pm - 4:10 pm
ORD
-
MAD
13h 55m
1 stop
Scandinavian Airlines Logo
5:00 pm - 4:45 pm
MAD
-
ORD
30h 45m
1 stop
$566Scandinavian Airlines
Tue, Aug 18 - Tue, Sep 8
Multiple Airlines Logo
7:25 pm - 9:10 pm
ORD
-
CIA
18h 45m
2 stops
Multiple Airlines Logo
1:20 pm - 6:15 pm
CIA
-
ORD
35h 55m
3 stops
$767Multiple Airlines
Sun, Aug 9 - Tue, Aug 25
Multiple Airlines Logo
11:05 am - 6:45 pm
ORD
-
CIA
24h 40m
3 stops
Multiple Airlines Logo
8:40 pm - 12:55 pm
CIA
-
ORD
23h 15m
2 stops
$777Multiple Airlines
Sun, Nov 1 - Wed, Nov 18
Multiple Airlines Logo
6:30 pm - 4:10 pm
ORD
-
CIA
14h 40m
2 stops
Multiple Airlines Logo
7:10 pm - 5:20 pm
CIA
-
ORD
29h 10m
3 stops
$780Multiple Airlines
Mon, Oct 19 - Wed, Oct 28
Multiple Airlines Logo
3:45 pm - 10:05 am
ORD
-
BVA
11h 20m
1 stop
Multiple Airlines Logo
1:15 pm - 6:20 pm
BVA
-
ORD
35h 05m
2 stops
$796Multiple 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

Tue, Sep 15 - Tue, Oct 13
Frontier Logo
7:25 am - 10:23 am
MDW
-
ATL
1h 58mnonstop
Frontier Logo
9:00 pm - 9:58 pm
ATL
-
MDW
1h 58mnonstop
$135Frontier
Wed, Sep 9 - Tue, Sep 15
Frontier Logo
7:25 am - 10:23 am
MDW
-
ATL
1h 58mnonstop
Frontier Logo
9:00 pm - 9:58 pm
ATL
-
MDW
1h 58mnonstop
$136Frontier
Tue, Sep 22 - Tue, Sep 29
Frontier Logo
12:03 pm - 3:03 pm
MDW
-
ATL
2h 00mnonstop
Frontier Logo
9:00 pm - 9:58 pm
ATL
-
MDW
1h 58mnonstop
$138Frontier
Wed, Sep 9 - Fri, Sep 11
Southwest Logo
5:10 am - 8:10 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$184Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
7:50 am - 11:00 am
MDW
-
LGA
2h 10mnonstop
Southwest Logo
6:00 am - 7:15 am
LGA
-
MDW
2h 15mnonstop
$187Southwest
Sat, Jul 25 - Sat, Aug 1
Southwest Logo
6:40 pm - 9:50 pm
MDW
-
LGA
2h 10mnonstop
Southwest Logo
5:35 pm - 7:25 pm
LGA
-
MDW
2h 50mnonstop
$189Southwest
Tue, Aug 11 - Wed, Aug 19
Delta Logo
5:10 pm - 12:10 am
MDW
-
EWR
6h 00m
1 stop
Delta Logo
7:05 am - 11:51 am
EWR
-
MDW
5h 46m
1 stop
$191Delta
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
5:25 am - 7:50 am
MDW
-
HOU
2h 25mnonstop
Southwest Logo
5:00 am - 7:25 am
HOU
-
MDW
2h 25mnonstop
$205Southwest
Wed, Sep 30 - Thu, Oct 1
Delta Logo
1:19 pm - 7:30 pm
MDW
-
EWR
5h 11m
1 stop
Delta Logo
9:48 am - 12:39 pm
EWR
-
MDW
3h 51m
1 stop
$207Delta
Tue, Aug 11 - Fri, Aug 14
Delta Logo
6:42 pm - 11:25 pm
MDW
-
EWR
3h 43m
1 stop
Delta Logo
1:00 pm - 6:33 pm
EWR
-
MDW
6h 33m
1 stop
$209Delta
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 (14% of total searches). The next most popular destinations are Dallas (11%) and Las Vegas Harry Reid Intl (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 Cancún, Mexico City and Tokyo.

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 (76% of total searches). The next most popular destinations are Canada (21%) and Dominican Republic (3%).

Which cities can I fly to direct from Chicago Midway Airport?

There are loads of places you can fly direct to from Chicago Midway Airport. The most popular destinations for direct flights among KAYAK users are Jacksonville, El Paso, St. Louis, Charlotte and Salt Lake City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Charleston at $227, while the most expensive was Salt Lake City, at $318.

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, San Luis Potosí and Cancún. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Toronto at $150, while the most expensive was León, at $341.

What is the longest direct flight from Chicago Midway Airport?

The longest direct flight you can take from Chicago Midway Airport is to Seattle, with a duration of 4h 45m. The next longest is Oakland at 4h 45m, followed by a flight to San Jose at 4h 45m.

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 Valparaiso and cost $49. The next cheapest destinations were Knoxville at $58 and Asheville at $58.

Good to know

Low seasonJanuary
Cheapest flight$81
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to Dallas/Fort Worth Airport

FAQs for booking flights out of Chicago Midway Airport

  • Are there any airlines that operate flights from Chicago Midway International Airport (MDW) and are known for being environmentally friendly?

    If being environmentally friendly is one of your priorities, you may want to fly with Delta. Delta has a goal to replace 10% of its standard aviation fuel with sustainable aviation fuel by the end of 2030.

  • How can I go from downtown Chicago to Chicago Midway International Airport (MDW)?

    To go from downtown Chicago to Chicago Midway International Airport (MDW), you can always choose to drive, which normally takes around 20 minutes in total. Public transportation is a convenient option as well, like bus line 55, which will bring you to the airport in around 10 to 15 minutes depending on how traffic is at the time.

  • Are there any airlines that have lounges for passengers at Chicago Midway International Airport (MDW)?

    There are no airlines that currently have lounges at Chicago Midway International Airport (MDW). However, the airport does have a USO Midway Lounge, which is reserved for past and present members of the military, as well as their family members. In this lounge, travelers will have access to free snacks and drinks, as well as shower facilities.

  • What services does Chicago Midway International Airport (MDW) offer for travelers with limited mobility or disabilities?

    Chicago Midway International Airport (MDW) has wheelchairs that all guests are able to use for free. The airport also has accessible restroom stalls, elevators, and ramps that can be used to go to different floors and terminals. If you will need additional help navigating the airport, make sure to contact your airline in advance.

  • What is Midway also known as?

    Chicago Midway Airport’s airport code is MDW. It can also be referred to as Chicago Midway, Chicago Midway Intl, Midway, Midway Intl.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to your destination with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding a cheap flight out of Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Atlanta $131 one-way - $218 round-trip; New York $165 one-way - $273 round-trip; Orlando $169 one-way - $320 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.
7.9
SouthwestOverall score based on 4246 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

6.0 GoodAnonymous, Jun 2026
MDW - BDL
Read more Southwest reviews

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

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.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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

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

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent experience. WiFi worked on this leg of My trip

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

This is a no frills, get it done, efficient airline. The seat is a lawn chair. You better bring your own entertainment. If you want something other than water you need to pay for it. But they will get you to your destination quickly, on time, and then they will turn the flight around and go right back where they came from. Reliably. Couple times a week tops. If it fits into your schedule, you can’t get there cheaper or faster.

A three hour delay to board and then another hour on the tarmac because they couldn't get a tractor? Ugh.

Allegiant canceled the flight. The flight the next day was full. Allegiant did not provide any compensation besides a refund. Last time on Allegiant.

Seats were very uncomfortable and being charged for snacks and water.........

Allegiant actually impressed me, original inbound flight from PBG was so late they gave us a bird inbound from Des Moines and only left 1h late and gained 40 minutes back in the air. Comfortable flight with no frills but no complaints.

Flight was delayed. Crew was good but hot coffee was not available.

Great. No choice for n/a. No food or entertainment options

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.

Posted a 20minute delay but didn’t delay at all. Caused boarding issues and confusion. Also, didn’t release baggage. Took over an hour and 20 minutes to get luggage.

I went to lower my tray table and it was very nasty. Looks like some one had left some food on it and then just closed it up.

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

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

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.

The app doesn’t work. I am having a lot of trouble checking in for flight tomorrow. Very disconcerting. Then they es t to charge extra for checking in at the airport;(

To many extra fees, poor customer service and very uncomfortable flight. No leg room and seat wont recline.

I am disabled and was unable to get any assistance from Volaris. I had to wait in line at front desk for 45 minutes, I am by myself, and unable to stand. When I got to front desk check in, they had no assistance for me. I did however, have wheelchair assistance when I arrived in Mexico City. Thank God for that!

Our flight got overbooked and we missed one day of our trip.

Be prepared to pay extra for everything! I'm not sure I really saved any money?

The flight was 3 hrs delayed and no remorse from airline

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 !!!!!!!

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

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Everything you need to know for your flight from Midway

Information on your arrival and departure airports