$39 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 6/20. 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 Thu 6/4 and returning Thu 6/11

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, Jul 7 - Sat, Jul 11
Frontier Logo
6:00 am - 9:49 am
ORD
-
CUN
3h 49mnonstop
Frontier Logo
11:00 am - 3:09 pm
CUN
-
ORD
4h 09mnonstop
$253Frontier
Sat, Jul 4 - Wed, Jul 8
Frontier Logo
6:00 am - 10:01 am
ORD
-
CUN
4h 01mnonstop
Frontier Logo
11:00 am - 3:09 pm
CUN
-
ORD
4h 09mnonstop
$258Frontier
Sat, May 16 - Sat, May 23
Frontier Logo
6:55 am - 2:07 pm
ORD
-
CUN
7h 12m
1 stop
Frontier Logo
1:14 pm - 11:01 pm
CUN
-
ORD
9h 47m
1 stop
$270Frontier
Sun, Aug 23 - Wed, Nov 4
TAP AIR PORTUGAL Logo
6:00 pm - 12:40 pm
ORD
-
MAD
11h 40m
1 stop
TAP AIR PORTUGAL Logo
7:40 am - 3:30 pm
MAD
-
ORD
14h 50m
1 stop
$626TAP AIR PORTUGAL
Sun, Aug 9 - Wed, Aug 26
TAP AIR PORTUGAL Logo
6:00 pm - 12:40 pm
ORD
-
MAD
11h 40m
1 stop
TAP AIR PORTUGAL Logo
7:40 am - 2:45 pm
MAD
-
ORD
14h 05m
1 stop
$627TAP AIR PORTUGAL
Sun, Aug 23 - Wed, Nov 4
TAP AIR PORTUGAL Logo
6:00 pm - 3:25 pm
ORD
-
MAD
14h 25m
1 stop
TAP AIR PORTUGAL Logo
7:40 am - 3:30 pm
MAD
-
ORD
14h 50m
1 stop
$629TAP AIR PORTUGAL
Wed, Oct 7 - Tue, Oct 20
Air Serbia Logo
4:40 pm - 9:10 am
ORD
-
BCN
33h 30m
1 stop
Air Serbia Logo
9:55 am - 2:30 pm
BCN
-
ORD
35h 35m
1 stop
$634Air Serbia
Sat, Oct 3 - Sat, Oct 10
Air Serbia Logo
11:20 pm - 9:10 am
ORD
-
BCN
26h 50m
1 stop
Air Serbia Logo
9:55 am - 9:15 pm
BCN
-
ORD
18h 20m
1 stop
$635Air Serbia
Wed, Aug 5 - Wed, Sep 16
TAP AIR PORTUGAL Logo
6:00 pm - 9:50 pm
ORD
-
BCN
20h 50m
1 stop
TAP AIR PORTUGAL Logo
10:40 pm - 12:40 pm
BCN
-
ORD
21h 00m
1 stop
$640TAP AIR PORTUGAL
Wed, Jun 3 - Wed, Jun 10
Multiple Airlines Logo
9:55 am - 3:35 pm
ORD
-
BVA
22h 40m
3 stops
Multiple Airlines Logo
5:55 am - 9:00 am
BVA
-
ORD
34h 05m
3 stops
$736Multiple 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

Thu, May 28 - Mon, Jun 1
Frontier Logo
6:00 am - 9:09 am
MDW
-
ATL
2h 09mnonstop
Frontier Logo
10:05 am - 11:09 am
ATL
-
MDW
2h 04mnonstop
$82Frontier
Thu, May 28 - Mon, Jun 1
Frontier Logo
6:00 am - 9:09 am
MDW
-
ATL
2h 09mnonstop
Frontier Logo
10:05 am - 11:09 am
ATL
-
MDW
2h 04mnonstop
$83Frontier
Wed, Jun 3 - Sat, Jun 6
Frontier Logo
12:04 pm - 3:10 pm
MDW
-
ATL
2h 06mnonstop
Frontier Logo
9:00 pm - 10:02 pm
ATL
-
MDW
2h 02mnonstop
$84Frontier
Sat, Jun 20 - Thu, Jun 25
Frontier Logo
4:10 pm - 6:53 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
12:49 pm - 3:15 pm
DFW
-
MDW
2h 26mnonstop
$113Frontier
Thu, Jun 4 - Mon, Jun 8
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$114Frontier
Thu, Jun 4 - Mon, Jun 8
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$115Frontier
Wed, May 20 - Wed, May 27
Multiple Airlines Logo
6:00 am - 1:14 pm
MDW
-
FLL
6h 14m
1 stop
Multiple Airlines Logo
3:11 pm - 10:02 pm
FLL
-
MDW
7h 51m
1 stop
$145Multiple Airlines
Thu, Jun 11 - Wed, Jun 17
Southwest Logo
5:15 am - 8:15 am
MDW
-
LGA
2h 00mnonstop
Southwest Logo
6:00 am - 7:20 am
LGA
-
MDW
2h 20mnonstop
$177Southwest
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
5:15 pm - 7:30 pm
MDW
-
LAX
4h 15mnonstop
Southwest Logo
11:55 pm - 5:55 am
LAX
-
MDW
4h 00mnonstop
$199Southwest
Wed, Aug 19 - Tue, Aug 25
Southwest Logo
9:25 am - 1:05 pm
MDW
-
LAX
5h 40m
1 stop
Southwest Logo
6:00 am - 12:00 pm
LAX
-
MDW
4h 00mnonstop
$205Southwest
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 (13% of total searches). The next most popular destinations are Dallas (13%) and Orlando (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, Paris and Cancún.

What are the most popular countries to fly to from Chicago Midway Airport?

The most popular countries KAYAK users have searched for from Chicago Midway Airport along with the average round-trip price for the route clicked by KAYAK users in the last 2 weeks.

Based on KAYAK flight searches, the most popular country to fly to from Chicago Midway Airport is Mexico (74% of total searches). The next most popular destinations are Canada (24%) 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 Los Angeles, El Paso, Charlotte, St. Louis 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 $253, while the most expensive was Salt Lake City, at $310.

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

There are many international destinations you can fly to non-stop from Chicago Midway Airport. The most popular international destinations from KAYAK users are Guadalajara, Morelia, León, Cancún and Toronto. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Toronto at $192, while the most expensive was León, at $465.

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 Punta Gorda and cost $21. The next cheapest destinations were Dallas at $40 and Asheville at $44.

Good to know

Low seasonJanuary
Cheapest flight$39
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago Midway Airport to Atlanta

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 $111 one-way - $161 round-trip; Dallas $167 one-way - $303 round-trip; Orlando $139 one-way - $285 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 4305 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

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

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

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

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

No food is available without purchasing it and there is no in-flight entertainment. Both of these are OK because we got an inexpensive flight from Allegiant and, otherwise, our experience was excellent.

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

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

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

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

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

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

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

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

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

The money you save flying volaris is not worth it

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

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

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

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

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

The flight was delayed by two hours. I had paid for extended leg room. Due to the delay, the plane was different and I didn't end up having extended leg room. I finally was able to reach Volaris on Whats App and they gave me an airline credit. I wanted a refund to the credit card since I hardly ever fly Volaris. Other than that, it was a very comfortable flight.

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

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

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

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

Everything you need to know for your flight from Midway

Information on your arrival and departure airports