$55 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 11/15. 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
$92
Overall average: $233
Frontier
Mon 12/8Fri 12/12
MDW - DFW • Non-stop
Cheapest one-way
$54
Typical prices: $78-$147
Frontier
Sat 11/15
MDW - DFW • 1 stop
Our travelers' advice
AI-generated summary based on content written by travel experts
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
Frontier
Cheapest • from $92 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-DFW
Cheapest • 42% average savings
MDW-DFW
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
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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

Mon, Dec 8 - Fri, Dec 12
Frontier Logo
12:35 pm - 3:05 pmMDW-DFW
2h 30mnonstop
Frontier Logo
11:47 am - 2:04 pmDFW-MDW
2h 17mnonstop
$92Frontier
Find Deal
Thu, Dec 4 - Mon, Dec 8
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
Frontier Logo
9:02 am - 11:20 amDFW-MDW
2h 18mnonstop
$93Frontier
Find Deal
Wed, Nov 19 - Sun, Nov 23
Frontier Logo
1:56 pm - 8:51 pmMDW-DFW
6h 55m1 stop
Frontier Logo
9:54 pm - 12:13 amDFW-MDW
2h 19mnonstop
$94Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
9:39 pm - 12:17 amMDW-DFW
2h 38mnonstop
Frontier Logo
2:43 pm - 5:01 pmDFW-MDW
2h 18mnonstop
$95Frontier
Find Deal
Thu, Nov 13 - Mon, Nov 17
Frontier Logo
9:39 pm - 12:17 amMDW-DFW
2h 38mnonstop
Frontier Logo
2:43 pm - 5:01 pmDFW-MDW
2h 18mnonstop
$96Frontier
Find Deal
Sun, Nov 16 - Mon, Nov 17
Frontier Logo
11:21 am - 1:56 pmMDW-DFW
2h 35mnonstop
Frontier Logo
1:44 pm - 10:11 pmDFW-MDW
8h 27m1 stop
$97Frontier
Find Deal
Fri, Dec 5 - Tue, Dec 23
Frontier Logo
8:05 am - 10:47 amMDW-DFW
2h 42mnonstop
Frontier Logo
11:42 am - 1:59 pmDFW-MDW
2h 17mnonstop
$98Frontier
Find Deal
Mon, Nov 10 - Thu, Nov 13
Frontier Logo
6:27 pm - 9:02 pmMDW-DFW
2h 35mnonstop
Frontier Logo
6:16 pm - 8:44 pmDFW-MDW
2h 28mnonstop
$99Frontier
Find Deal
Thu, Jan 8 - Thu, Jan 15
Southwest Logo
4:25 pm - 6:55 pmMDW-DAL
2h 30mnonstop
Southwest Logo
10:40 am - 12:50 pmDAL-MDW
2h 10mnonstop
$117Southwest
Find Deal
Sat, Dec 13 - Sat, Jan 10
Southwest Logo
6:25 am - 8:50 amMDW-DAL
2h 25mnonstop
Southwest Logo
2:30 pm - 4:40 pmDAL-MDW
2h 10mnonstop
$137Southwest
Find Deal
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 $78 on the route between Chicago Midway Airport (MDW) and Dallas/Fort Worth Airport (DFW). Over the past month, this route was, on average, 42% cheaper than other Chicago Midway Airport-Dallas routes. It is also the most popular route.

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 Wednesday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Mondays 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 $169 (return) on average. On the other hand, the most expensive months are September and December, where the average cost of round-trip tickets is $259 and $233 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 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 9 weeks before departure.

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Expert advice

Expert advice for your flight from Midway to Dallas

 
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

Frontier's Premium Bundle offers priority boarding and extra legroom for just $20 more than Economy.


Avoid middle seats by selecting Economy Bundle for free Standard seat selection and carry-on bag.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest's Rapid Rewards offers unlimited rewards seats and points that don’t expire.


Southwest's Love Field offers a smaller, easier-to-navigate airport experience.

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

Good to know

Cheapest flight$54
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 $54 for a one-way ticket and $92 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

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

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

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 4242 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Full cans of soda would be nice. A choice between two snacks would be appreciated.

8.0 ExcellentMargaret, Oct 2025SAV - HOU
Read more Southwest reviews

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

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

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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