MDW

$54 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 5/19. 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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41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$113
Typical prices: $309-$173
Frontier
Tue 5/12Wed 5/13
DFW - MDW • Non-stop
Cheapest one-way
$54
Typical prices: $109-$170
Frontier
Tue 5/19
DFW - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Cheapest • from $113 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Frontier and Southwest. Average duration is 2h 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 44% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 78% on-time
Best time • Fewest delays
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 32% compared to booking last minute.
Insights
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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!
Flight Deals
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Expert advice
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

Tue, May 12 - Wed, May 13
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$113Frontier
Mon, Jun 1 - Thu, Jun 4
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$114Frontier
Sat, Jun 13 - Sat, Jun 20
Frontier Logo
12:49 pm - 3:15 pm
DFW
-
MDW
2h 26mnonstop
Frontier Logo
4:10 pm - 6:53 pm
MDW
-
DFW
2h 43mnonstop
$116Frontier
Tue, May 19 - Thu, May 28
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$117Frontier
Thu, May 28 - Fri, Jun 5
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$120Frontier
Sat, Jun 13 - Sat, Jun 20
Frontier Logo
12:49 pm - 3:15 pm
DFW
-
MDW
2h 26mnonstop
Frontier Logo
4:10 pm - 6:53 pm
MDW
-
DFW
2h 43mnonstop
$121Frontier
Sat, May 30 - Sat, Jun 6
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
5:37 pm - 8:20 pm
MDW
-
DFW
2h 43mnonstop
$122Frontier
Tue, May 12 - Wed, May 13
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
$124Frontier
Thu, Jun 11 - Sun, Jun 14
Southwest Logo
10:50 pm - 1:00 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
5:00 am - 7:15 am
MDW
-
DAL
2h 15mnonstop
$245Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
1:10 pm - 3:25 pm
DAL
-
MDW
2h 15mnonstop
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
DAL
2h 15mnonstop
$250Southwest
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.

How much is a round-trip flight from Dallas to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Dallas to Chicago Midway Airport departing in May.

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 $93 on the route between Dallas/Fort Worth Airport (DFW) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 44% cheaper than other Dallas-Chicago Midway Airport routes. The most popular route is between Dallas Love Field Airport (DAL) and Chicago Midway Airport (MDW).

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 Fridays 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 May, where tickets cost $39 (return) on average. On the other hand, the most expensive months are July and November, where the average cost of round-trip tickets is $111 and $103 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 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Expert advice

Expert advice for your flight from Dallas to Midway

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

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.

Blane Bachelor

Blane Bachelor

Expert on Southwest

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.

Good to know

Cheapest flight$54
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 $54 for a one-way ticket and $113 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 4314 reviews
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
7.0Food
Airline reviews

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

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

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.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I elected to pay for the upgrades and found very little difference

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!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

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

Information on your arrival and departure airports