$49 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 4/3. 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 Mon 2/23 and returning Mon 3/2

Book Cheap International Flights from Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip international flight deals from Midway to anywhere

Sun, Mar 1 - Fri, Mar 6
Spirit Airlines Logo
6:05 am - 10:54 am
ORD
-
CUN
3h 49mnonstop
Spirit Airlines Logo
11:59 am - 2:53 pm
CUN
-
ORD
3h 54mnonstop
$226Spirit Airlines
Tue, Feb 3 - Fri, Feb 6
Multiple Airlines Logo
6:23 am - 9:26 pm
ORD
-
CUN
14h 03m
1 stop
Multiple Airlines Logo
1:21 pm - 7:38 pm
CUN
-
ORD
7h 17m
1 stop
$227Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
6:05 am - 10:54 am
ORD
-
CUN
3h 49mnonstop
Multiple Airlines Logo
6:27 pm - 9:37 pm
CUN
-
ORD
4h 10mnonstop
$228Multiple Airlines
Mon, Feb 9 - Wed, Mar 11
Multiple Airlines Logo
7:15 am - 9:35 am
ORD
-
BCN
19h 20m
1 stop
Multiple Airlines Logo
11:55 am - 7:25 pm
BCN
-
ORD
13h 30m
1 stop
$420Multiple Airlines
Sat, Mar 21 - Tue, Mar 31
United Airlines Logo
9:15 pm - 8:20 am
ORD
-
BCN
29h 05m
1 stop
United Airlines Logo
1:15 pm - 12:17 pm
BCN
-
ORD
30h 02m
2 stops
$421United Airlines
Wed, Feb 18 - Wed, Feb 25
British Airways Logo
4:05 pm - 6:25 pm
ORD
-
BCN
19h 20m
2 stops
British Airways Logo
10:40 am - 11:36 pm
BCN
-
ORD
19h 56m
1 stop
$422British Airways
Wed, Apr 1 - Wed, Apr 8
Multiple Airlines Logo
7:25 pm - 9:50 pm
ORD
-
BVA
19h 25m
2 stops
Multiple Airlines Logo
5:55 am - 6:15 pm
BVA
-
ORD
19h 20m
2 stops
$468Multiple Airlines
Sun, Mar 1 - Tue, Mar 10
United Airlines Logo
5:55 pm - 4:40 pm
ORD
-
MAD
15h 45m
1 stop
United Airlines Logo
12:40 pm - 1:15 pm
MAD
-
ORD
30h 35m
2 stops
$474United Airlines
Fri, Feb 20 - Wed, Feb 25
British Airways Logo
5:40 pm - 8:50 am
ORD
-
MAD
8h 10mnonstop
British Airways Logo
12:00 pm - 2:55 pm
MAD
-
ORD
9h 55mnonstop
$475British Airways
Sun, Mar 1 - Tue, Mar 10
United Airlines Logo
7:10 am - 9:15 am
ORD
-
MAD
19h 05m
1 stop
United Airlines Logo
9:05 am - 4:20 pm
MAD
-
ORD
13h 15m
1 stop
$476United 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

Fri, Feb 20 - Fri, Feb 27
Frontier Logo
7:45 am - 10:37 am
MDW
-
DFW
2h 52mnonstop
Frontier Logo
11:37 am - 1:53 pm
DFW
-
MDW
2h 16mnonstop
$87Frontier
Thu, Mar 5 - Sun, Mar 8
Frontier Logo
3:00 pm - 5:46 pm
MDW
-
DFW
2h 46mnonstop
Frontier Logo
10:30 pm - 12:49 am
DFW
-
MDW
2h 19mnonstop
$89Frontier
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
1:00 pm - 3:19 pm
DFW
-
MDW
2h 19mnonstop
$90Frontier
Mon, Mar 9 - Mon, Mar 16
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$91Frontier
Mon, Mar 9 - Mon, Mar 16
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$92Frontier
Sat, Mar 7 - Thu, Mar 12
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$99Frontier
Sun, Feb 15 - Thu, Feb 19
Frontier Logo
7:30 am - 11:20 am
MDW
-
MCO
2h 50mnonstop
Frontier Logo
12:20 pm - 2:26 pm
MCO
-
MDW
3h 06mnonstop
$101Frontier
Sat, May 2 - Sat, May 9
Frontier Logo
9:14 am - 1:03 pm
MDW
-
MCO
2h 49mnonstop
Frontier Logo
2:13 pm - 4:13 pm
MCO
-
MDW
3h 00mnonstop
$102Frontier
Sat, Feb 7 - Thu, Feb 12
Multiple Airlines Logo
9:38 am - 7:38 pm
MDW
-
FLL
9h 00m
1 stop
Multiple Airlines Logo
6:07 pm - 10:34 pm
FLL
-
MDW
5h 27m
1 stop
$131Multiple Airlines
Sat, Feb 21 - Thu, Feb 26
Southwest Logo
6:00 pm - 9:45 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:35 am - 8:35 am
RSW
-
MDW
3h 00mnonstop
$168Southwest
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 (8% of total searches). The next most popular destinations are Dallas (8%) and Fort Lauderdale (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, Punta Cana 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 (81% of total searches). The next most popular destinations are Canada (15%) and Dominican Republic (2%).

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

There are loads of places you can fly direct to from Chicago Midway Airport. The most popular destinations for direct flights among KAYAK users are Jacksonville, Los Angeles, Charlotte, Salt Lake City and Charleston. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Charleston at $228, while the most expensive was Jacksonville, at $289.

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 $218, while the most expensive was Durango, at $488.

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 55m. The next longest is Oakland at 4h 35m, followed by a flight to San Francisco at 4h 35m.

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 Dallas and cost $29. The next cheapest destinations were Miami at $29 and Phoenix at $33.

Good to know

Low seasonAugust
Cheapest flight$49
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 3% 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 $133 one-way - $180 round-trip; Orlando $117 one-way - $164 round-trip; Phoenix $113 one-way - $205 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 4270 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Great vacation. Can't wait till next year for another one.

10.0 ExcellentJohn, Jan 2026
SAT - PHX
Read more Southwest reviews

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

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

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

Check in on the web portal was cumbersome! After several attempts I finally got the boarding pass.

Excellent flight and even arrived 23 min early. No entertainment , or wi fi on board, but I downloaded a couple of movies beforehand which kept me entertained. Really like flying Allegiant airlines.

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

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

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

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

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

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.

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

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

Everything you need to know for your flight from Midway

Information on your arrival and departure airports