MDW

$42 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 1/26. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$83
Overall average: $196
Frontier
Fri 1/30Mon 2/2
DFW - MDW • Non-stop
Cheapest one-way
$42
Typical prices: $84-$188
Frontier
Mon 1/26
DFW - MDW • Non-stop
Our travelers' advice
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
Frontier
Cheapest • from $88 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DFW-MDW
Cheapest • 21% average savings
DFW-MDW
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 35% compared to booking last minute.
Insights
Insights
Insights
Insights
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
Booking Insights
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

Fri, Jan 30 - Mon, Feb 2
Frontier Logo
1:30 pm - 3:49 pm
DFW
-
MDW
2h 19mnonstop
Frontier Logo
9:45 am - 12:30 pm
MDW
-
DFW
2h 45mnonstop
$83Frontier
Fri, Jan 16 - Mon, Jan 19
Frontier Logo
2:05 pm - 4:23 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
$84Frontier
Thu, Feb 19 - Fri, Feb 20
Frontier Logo
6:56 pm - 9:12 pm
DFW
-
MDW
2h 16mnonstop
Frontier Logo
7:45 am - 10:37 am
MDW
-
DFW
2h 52mnonstop
$85Frontier
Fri, Jan 16 - Sun, Jan 18
Frontier Logo
2:05 pm - 4:23 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
11:05 am - 1:48 pm
MDW
-
DFW
2h 43mnonstop
$86Frontier
Fri, Jan 23 - Sun, Feb 1
Frontier Logo
1:30 pm - 3:49 pm
DFW
-
MDW
2h 19mnonstop
Frontier Logo
5:13 pm - 8:00 pm
MDW
-
DFW
2h 47mnonstop
$87Frontier
Wed, Feb 18 - Sat, Feb 21
Frontier Logo
9:45 am - 7:07 pm
DFW
-
MDW
9h 22m1 stop
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
$93Frontier
Sun, Jan 11 - Sun, Jan 18
Frontier Logo
1:00 pm - 3:18 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
11:05 am - 1:48 pm
MDW
-
DFW
2h 43mnonstop
$94Frontier
Fri, Jan 16 - Sun, Jan 18
Frontier Logo
2:05 pm - 4:23 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
11:05 am - 1:48 pm
MDW
-
DFW
2h 43mnonstop
$95Frontier
Tue, Jan 20 - Wed, Jan 21
Southwest Logo
4:50 pm - 7:00 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
8:00 pm - 10:25 pm
MDW
-
DAL
2h 25mnonstop
$151Southwest
Sat, Feb 21 - Sat, Feb 28
Southwest Logo
7:05 am - 9:15 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
9:20 am - 11:50 am
MDW
-
DAL
2h 30mnonstop
$157Southwest
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 $75 on the route between Dallas/Fort Worth Airport (DFW) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 21% 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 November, where the average cost of round-trip tickets is $247 and $223 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.

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.
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.

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.

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$42
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 $42 for a one-way ticket and $83 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

Southwest

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

Southwest

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.
7.9
SouthwestOverall score based on 4249 reviews
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
Airline reviews

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

10.0 ExcellentAnonymous, Dec 2025
DAL - LAX
Read more Southwest reviews

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

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.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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

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

Information on your arrival and departure airports