$43 Find Cheap Flights from Chicago Midway Airport to Dallas

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Dallas departing on 5/16. 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 Dallas

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Dallas, 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 Chicago to Dallas, 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
$99
Overall average: $209
Frontier
Tue 5/19Sun 5/24
MDW - DFW • Non-stop
Cheapest one-way
$43
Typical prices: $73-$233
Frontier
Sat 5/16
MDW - DFW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest's two free checked bags suit luggage needs.
Frontier's Premium Bundle adds legroom for $20 more.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $99 (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 30m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 39% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 84% on-time
Best time • Fewest delays
Insights
Insights
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Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 40% compared to booking last minute.
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Flight Deals
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Flight Deals

Cheap Flights from Midway to Dallas (MDW-DFW)

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

Tue, May 19 - Sun, May 24
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$99Frontier
Tue, May 5 - Fri, May 8
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$100Frontier
Tue, May 19 - Tue, May 26
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$102Frontier
Thu, Apr 30 - Sun, May 3
Frontier Logo
8:25 am - 11:14 am
MDW
-
DFW
2h 49mnonstop
Frontier Logo
7:55 pm - 10:15 pm
DFW
-
MDW
2h 20mnonstop
$103Frontier
Wed, Jun 10 - Sat, Jun 13
Frontier Logo
9:11 pm - 11:58 pm
MDW
-
DFW
2h 47mnonstop
Frontier Logo
5:43 pm - 8:06 pm
DFW
-
MDW
2h 23mnonstop
$105Frontier
Sat, Jul 18 - Sat, Aug 8
Frontier Logo
9:11 pm - 11:58 pm
MDW
-
DFW
2h 47mnonstop
Frontier Logo
5:43 pm - 8:06 pm
DFW
-
MDW
2h 23mnonstop
$106Frontier
Wed, May 20 - Mon, Jun 8
Frontier Logo
3:07 pm - 5:50 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$107Frontier
Thu, Apr 30 - Wed, May 6
Frontier Logo
8:25 am - 11:14 am
MDW
-
DFW
2h 49mnonstop
Frontier Logo
11:55 am - 2:12 pm
DFW
-
MDW
2h 17mnonstop
$108Frontier
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
4:00 pm - 6:25 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
6:05 pm - 8:20 pm
DAL
-
MDW
2h 15mnonstop
$177Southwest
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
8:45 pm - 11:10 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
1:30 pm - 4:50 pm
DAL
-
MDW
3h 20m
1 stop
$183Southwest
Booking Insights

KAYAK's insights & trends for Midway to Dallas flights

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

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

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

The cheapest return flight from Chicago Midway Airport to Dallas costs $82 on the route between Chicago Midway Airport (MDW) and Dallas/Fort Worth Airport (DFW). Over the past month, this route was, on average, 39% cheaper than other Chicago Midway Airport-Dallas routes. The most popular route is between Chicago Midway Airport (MDW) and Dallas Love Field Airport (DAL).

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

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

Your flight ticket price will generally be cheaper if you fly to Dallas on a Saturday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Tuesdays for better deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Dallas, 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 Chicago Midway Airport to Dallas is October, where tickets cost $166 (return) on average. On the other hand, the most expensive months are September and November, where the average cost of round-trip tickets is $258 and $251 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to Dallas, 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 Chicago Midway Airport to Dallas, you should book around 3 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Expert advice

Expert advice for your flight from Midway to Dallas

 
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
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.

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.

Good to know

Cheapest flight$43
Flight from Chicago Midway Airport to Dallas/Fort Worth Airport

When to book flights from Midway to Dallas

Are your dates flexible? Find out the best times to travel from Midway to Dallas 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 Chicago Midway Airport to Dallas flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Dallas was $43 for a one-way ticket and $99 for a round-trip.

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

    Yes

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

    When flying out of Chicago Midway Airport you will be using Chicago Midway. You will be landing at one of these airports: Dallas Love Field or Dallas/Fort Worth.

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

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

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

    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 Chicago Midway Airport to Dallas.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Dallas from Chicago Midway Airport 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 Chicago Midway Airport to Dallas?

    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 Dallas with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Dallas?

    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 Dallas from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Prefer to fly direct from Chicago Midway Airport to Dallas?

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

Direct departures

Chicago Midway to Dallas

Monday

Frontier,Southwest

Frontier,Southwest

Tuesday

Southwest,Frontier

Southwest,Frontier

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

Dallas to Chicago Midway

Monday

Frontier,Southwest

Frontier,Southwest

Tuesday

Southwest,Frontier

Southwest,Frontier

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 Midway to Dallas

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Dallas. 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 Midway to Dallas? 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 4318 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

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

6.0 GoodChris, Mar 2026
DAL - SAT
Read more Southwest reviews

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

The new seating arrangement is so over priced for what you get.

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No delays and arrived to destination 30 min early. Staff was super friendly.

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.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

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

Information on your arrival and departure airports