$49 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 3/19. 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 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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Everything you should know

Cheapest round-trip
$88
Overall average: $197
Frontier
Sat 3/14Sun 3/22
MDW - DFW • Non-stop
Cheapest one-way
$49
Typical prices: $56-$184
Frontier
Thu 3/19
MDW - DFW • Non-stop
Our travelers' advice
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
Frontier
Cheapest • from $116 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-DFW
Cheapest • 53% 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 34% compared to booking last minute.
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

Sat, Mar 14 - Sun, Mar 22
Frontier Logo
9:16 pm - 11:59 pm
MDW
-
DFW
2h 43mnonstop
Frontier Logo
10:29 pm - 12:48 am
DFW
-
MDW
2h 19mnonstop
$88Frontier
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
1:00 pm - 3:19 pm
DFW
-
MDW
2h 19mnonstop
$90Frontier
Sat, Feb 21 - Wed, Feb 25
Frontier Logo
9:15 am - 12:00 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
9:45 am - 7:07 pm
DFW
-
MDW
9h 22m1 stop
$93Frontier
Mon, Feb 9 - Wed, Feb 11
Frontier Logo
9:45 am - 12:30 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
9:45 am - 7:07 pm
DFW
-
MDW
9h 22m1 stop
$94Frontier
Mon, Feb 2 - Wed, Mar 4
Frontier Logo
9:45 am - 12:30 pm
MDW
-
DFW
2h 45mnonstop
Frontier Logo
9:45 am - 7:07 pm
DFW
-
MDW
9h 22m1 stop
$95Frontier
Fri, Feb 27 - Sat, Feb 28
Frontier Logo
7:45 am - 10:37 am
MDW
-
DFW
2h 52mnonstop
Frontier Logo
1:00 pm - 3:19 pm
DFW
-
MDW
2h 19mnonstop
$97Frontier
Fri, Feb 20 - Sat, Feb 21
Frontier Logo
7:45 am - 10:37 am
MDW
-
DFW
2h 52mnonstop
Frontier Logo
10:44 am - 9:33 pm
DFW
-
MDW
10h 49m1 stop
$98Frontier
Thu, Feb 26 - Sat, Feb 28
Frontier Logo
3:00 pm - 5:46 pm
MDW
-
DFW
2h 46mnonstop
Frontier Logo
10:44 am - 9:39 pm
DFW
-
MDW
10h 55m1 stop
$99Frontier
Thu, Feb 5 - Mon, Feb 9
Southwest Logo
7:40 am - 10:15 am
MDW
-
DAL
2h 35mnonstop
Southwest Logo
6:35 am - 8:45 am
DAL
-
MDW
2h 10mnonstop
$143Southwest
Wed, Feb 11 - Wed, Feb 18
Southwest Logo
1:30 pm - 7:00 pm
MDW
-
DAL
5h 30m1 stop
Southwest Logo
7:00 am - 9:10 am
DAL
-
MDW
2h 10mnonstop
$149Southwest
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 $57 on the route between Chicago Midway Airport (MDW) and Dallas/Fort Worth Airport (DFW). Over the past month, this route was, on average, 53% 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 Friday and more expensive on a Monday. 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 $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 $259 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 2 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 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.
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.

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.

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$49
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 $49 for a one-way ticket and $88 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

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

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

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 4254 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

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

10.0 ExcellentIlevba, Nov 2025
DCA - DAL
Read more Southwest reviews

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

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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.

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.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

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

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