MDW

$31 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 10/24. 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

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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Flights 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

Thu, Oct 2 - Sat, Oct 4
Frontier Logo
6:55 am - 9:18 amDFW-MDW
2h 23mnonstop
Frontier Logo
11:23 am - 1:59 pmMDW-DFW
2h 36mnonstop
$59Frontier
Find Deal
Thu, Sep 4 - Mon, Sep 8
Frontier Logo
6:55 am - 9:18 amDFW-MDW
2h 23mnonstop
Frontier Logo
9:47 pm - 12:21 amMDW-DFW
2h 34mnonstop
$120Frontier
Find Deal
Fri, Oct 10 - Mon, Oct 13
Frontier Logo
9:52 pm - 12:11 amDFW-MDW
2h 19mnonstop
Frontier Logo
6:00 am - 8:39 amMDW-DFW
2h 39mnonstop
$135Frontier
Find Deal
Wed, Oct 8 - Tue, Oct 14
Frontier Logo
9:52 pm - 12:11 amDFW-MDW
2h 19mnonstop
Frontier Logo
8:00 am - 10:33 amMDW-DFW
2h 33mnonstop
$136Frontier
Find Deal
Wed, Oct 8 - Wed, Oct 22
Southwest Logo
12:35 pm - 2:45 pmDAL-MDW
2h 10mnonstop
Southwest Logo
5:30 am - 7:45 amMDW-DAL
2h 15mnonstop
$157Southwest
Find Deal
Wed, Aug 27 - Wed, Sep 3
Southwest Logo
7:20 pm - 9:30 pmDAL-MDW
2h 10mnonstop
Southwest Logo
12:50 pm - 3:05 pmMDW-DAL
2h 15mnonstop
$159Southwest
Find Deal
Sat, Aug 23 - Tue, Aug 26
Southwest Logo
4:45 pm - 7:00 pmDAL-MDW
2h 15mnonstop
Southwest Logo
8:30 am - 10:50 amMDW-DAL
2h 20mnonstop
$161Southwest
Find Deal
Sat, Aug 30 - Sat, Sep 6
Delta Logo
4:00 pm - 9:12 pmDFW-MDW
5h 12m1 stop
Delta Logo
10:31 am - 5:13 pmMDW-DFW
6h 42m1 stop
$197Delta
Find Deal
Thu, Aug 21 - Tue, Aug 26
Delta Logo
5:25 am - 11:48 amDFW-MDW
6h 23m1 stop
Delta Logo
6:17 pm - 11:01 pmMDW-DFW
4h 44m1 stop
$199Delta
Find Deal
Sun, Sep 14 - Sat, Sep 20
Delta Logo
5:39 am - 12:28 pmDFW-MDW
6h 49m1 stop
Delta Logo
9:20 am - 5:20 pmMDW-DFW
8h 00m1 stop
$207Delta
Find Deal
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

Two free checked bags up to 50 pounds each save money on baggage fees.


Download the Southwest app to access free in-flight entertainment and messaging.

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
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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Dallas to Chicago Midway Airport.

Our data shows that the cheapest route for a return flight from Dallas to Chicago Midway Airport cost $78 and was between Dallas/Fort Worth Airport (DFW) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $78.

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 Saturdays and the most expensive ones on Mondays.

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 September, where tickets cost $158 (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 2 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Cheapest flight$31
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 $31 for a one-way ticket and $59 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.

  • Which airline alliances offer flights from Dallas to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Dallas and Chicago Midway Airport.

  • 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 4241 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

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.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

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

Plz don't take away free bags and free seating

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

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

Information on your arrival and departure airports

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