MDW

$55 Find Cheap Flights from Dallas to 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 Dallas to Midway departing on 1/19. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Dallas to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Dallas to 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 flight deals from Dallas to Midway

Sat, Nov 15 - Sun, Nov 16
Frontier Logo
2:54 pm - 9:35 pmDFW-MDW
6h 41m1 stop
Frontier Logo
11:21 am - 1:56 pmMDW-DFW
2h 35mnonstop
$97Frontier
Find Deal
Thu, Nov 13 - Fri, Nov 14
Frontier Logo
8:36 am - 6:39 pmDFW-MDW
10h 03m1 stop
Frontier Logo
6:29 pm - 9:04 pmMDW-DFW
2h 35mnonstop
$98Frontier
Find Deal
Fri, Feb 20 - Mon, Feb 23
Frontier Logo
10:10 am - 7:50 pmDFW-MDW
9h 40m1 stop
Frontier Logo
7:00 am - 9:43 amMDW-DFW
2h 43mnonstop
$100Frontier
Find Deal
Mon, Nov 17 - Thu, Nov 20
Frontier Logo
2:43 pm - 5:01 pmDFW-MDW
2h 18mnonstop
Frontier Logo
5:30 am - 8:15 amMDW-DFW
2h 45mnonstop
$101Frontier
Find Deal
Thu, Nov 27 - Thu, Dec 4
Frontier Logo
9:54 pm - 12:13 amDFW-MDW
2h 19mnonstop
Frontier Logo
2:16 pm - 5:17 pmMDW-DFW
27h 01m1 stop
$102Frontier
Find Deal
Thu, Dec 11 - Sun, Dec 14
Frontier Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
$103Frontier
Find Deal
Sat, Jan 24 - Mon, Jan 26
Southwest Logo
11:20 am - 1:30 pmDAL-MDW
2h 10mnonstop
Southwest Logo
4:25 pm - 6:55 pmMDW-DAL
2h 30mnonstop
$117Southwest
Find Deal
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
12:55 pm - 4:25 pmDAL-MDW
3h 30m1 stop
Southwest Logo
8:30 pm - 10:55 pmMDW-DAL
2h 25mnonstop
$142Southwest
Find Deal
Sat, Dec 13 - Sun, Dec 14
Multiple Airlines Logo
12:20 pm - 9:22 pmDFW-MDW
9h 02m1 stop
Multiple Airlines Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
$142Multiple Airlines
Find Deal
Wed, Nov 19 - Thu, Nov 27
Delta Logo
6:40 pm - 11:40 pmDAL-MDW
5h 00m1 stop
Delta Logo
5:34 pm - 11:52 pmMDW-DAL
6h 18m1 stop
$198Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Southwest offers two free checked bags up to 50 lbs.
Frontier's Economy Bundle includes a carry-on bag.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $97 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DFW-MDW
Cheapest • 28% average savings
DFW-MDW
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
Cheapest round-trip
$97
Overall average: $178
Frontier
Sat 11/15Sun 11/16
DFW - MDW • 1 stop
Cheapest non-stop
$97
Typical prices: $138-$267
Frontier
Mon 11/17Thu 11/27
DFW - MDW • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Booking Insights

KAYAK's insights & trends for Dallas to Midway flights

Get data-powered insights and trends into flights from Dallas to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Dallas to Chicago Midway Airport flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Dallas to Chicago Midway Airport costs $81 on the route between Dallas/Fort Worth Airport (DFW) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 28% cheaper than other Dallas-Chicago Midway Airport routes. It is also the most popular route.

What’s the cheapest day of the week to fly from Dallas to Chicago Midway Airport?

The average price of all round-trip flights from Dallas to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from Dallas to Chicago Midway Airport, you should consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Dallas, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.

What is the cheapest month to fly from Dallas to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Dallas to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Dallas to Chicago Midway Airport is February, where tickets cost $168 (return) on average. On the other hand, the most expensive months are May and December, where the average cost of round-trip tickets is $247 and $228 respectively.

How far in advance should I book a flight from Dallas to Chicago Midway Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Dallas to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Dallas to Chicago Midway Airport, you should book around 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Expert advice

Expert advice for your flight from Dallas to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Economy Bundle includes a carry-on bag and no change fees, ideal for budget travelers.


Pay for bags online to save money; airport fees are higher.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers free carry-on and personal item, but checked bags now incur fees.


Southwest's Rapid Rewards program offers unlimited rewards seats and no blackout dates.

Read more about Southwestby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Good to know

Cheapest flight$49
Flight from Dallas/Fort Worth Airport to Chicago Midway Airport

When to book flights from Dallas to Midway

Are your dates flexible? Find out the best times to travel from Dallas to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Dallas to Chicago Midway Airport flights

  • What is the cheapest flight from Dallas to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Dallas to Chicago Midway Airport was $49 for a one-way ticket and $97 for a round-trip.

  • Do I need a passport to fly between Dallas and Chicago Midway Airport?

    A passport is required to fly from Dallas to Chicago Midway Airport.

  • Which airports will I be using when flying from Dallas to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from one of these Dallas airports: Dallas Love Field or Dallas/Fort Worth. You’ll be landing at Chicago Midway.

  • Which aircraft models fly most regularly from Dallas to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • How does KAYAK find such low prices on flights from Dallas to 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 Dallas to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Dallas 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 Dallas to 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 Chicago Midway Airport with an airline and back to Dallas with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Dallas to 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 to Chicago Midway Airport from Dallas up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Dallas to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Dallas to Chicago Midway.
Find which airlines fly direct from Dallas to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Dallas to Chicago Midway

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Direct returns

Chicago Midway to Dallas

Monday

Frontier, Southwest

Frontier, Southwest

Tuesday

Frontier, Southwest

Frontier, Southwest

Wednesday

Frontier, Southwest

Frontier, Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Frontier, Southwest

Frontier, Southwest

Saturday

Frontier, Southwest

Frontier, Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Reviews of the top airlines flying from Dallas to Midway

 
See real verified KAYAK customer reviews for airlines flying from Dallas to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Dallas to Midway? 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 4242 reviews
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
8.6Crew
Airline reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

2.0 MediocreThomas, Oct 2025SAT - STL
Read more Southwest reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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.

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

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

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

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

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

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

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.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Everything you need to know for your flight from Dallas to Midway

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