MDW

$61 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 4/19. 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
$82
Overall average: $219
Frontier
Thu 4/23Mon 4/27
DFW - MDW • Non-stop
Cheapest one-way
$61
Typical prices: $86-$144
Frontier
Sun 4/19
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 $82 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
DFW
-
MDW
Cheapest • 46% 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 38% 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
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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

Thu, Apr 23 - Mon, Apr 27
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$82Frontier
Thu, Apr 30 - Mon, May 4
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$83Frontier
Thu, May 7 - Mon, May 11
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$84Frontier
Mon, Apr 6 - Fri, Apr 10
Frontier Logo
8:55 pm - 11:13 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
5:11 pm - 8:00 pm
MDW
-
DFW
2h 49mnonstop
$85Frontier
Thu, Apr 9 - Mon, Apr 13
Frontier Logo
8:55 pm - 11:13 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
5:11 pm - 8:00 pm
MDW
-
DFW
2h 49mnonstop
$90Frontier
Thu, Feb 26 - Sat, Feb 28
Frontier Logo
10:45 am - 4:16 pm
DFW
-
MDW
5h 31m
1 stop
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
$97Frontier
Fri, Apr 24 - Sun, Apr 26
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$98Frontier
Fri, May 1 - Mon, May 4
Frontier Logo
8:03 pm - 10:21 pm
DFW
-
MDW
2h 18mnonstop
Frontier Logo
4:09 pm - 7:03 pm
MDW
-
DFW
2h 54mnonstop
$99Frontier
Tue, Mar 3 - Sat, Mar 7
Southwest Logo
10:25 am - 12:35 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
7:00 pm - 9:30 pm
MDW
-
DAL
2h 30mnonstop
$157Southwest
Tue, Mar 3 - Sat, Mar 7
Southwest Logo
1:50 pm - 7:05 pm
DAL
-
MDW
5h 15m
1 stop
Southwest Logo
12:35 pm - 3:05 pm
MDW
-
DAL
2h 30mnonstop
$167Southwest
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 $61 on the route between Dallas/Fort Worth Airport (DFW) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 46% 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 Saturdays 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 $155 (return) on average. On the other hand, the most expensive months are May and November, where the average cost of round-trip tickets is $248 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 38% 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.
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$61
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 $61 for a one-way ticket and $82 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

Southwest

Southwest

Wednesday

Southwest, Frontier

Southwest, Frontier

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

Southwest

Southwest

Wednesday

Southwest, Frontier

Southwest, Frontier

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 4267 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

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

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

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

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

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

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 Dallas to Midway

Information on your arrival and departure airports