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Midway

$50+ Cheap flights from Dallas to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
DFW — MDW
nov. 19 — nov. 261
mer. 11/19
mer. 11/26
1 adult, Economy
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Cheapflights Tip: The best prices from Dallas to Chicago Midway are usually found in February or September, booked 87 days in advance, depart on a Saturday or Tuesday and return on a Monday

Cheap flight deals from Dallas to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Dallas (A78) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated octobre 20, 2025.

Round-trip from

$100
(Kiwi.com)

One-way from

$50
(Southwest)

Popular in

May

Cheapest in

February

Average price

$186
From Dallas to Chicago Midway
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One-way flight from Dallas to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Dallas to Midway

Cheapest flights from Dallas to Midway
Explore the most affordable flight options available from Dallas to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octobre 20, 2025.

This CheapOair deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/59:15 amDFW - MDW
1 stop23h 57mFrontier
jeu. 11/69:34 pmMDW - DFW
Nonstop2h 38mFrontier
Deal found 10/20$100
This CheapOair deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 10/312:57 pmDFW - MDW
Nonstop2h 18mFrontier
lun. 11/1012:30 pmMDW - DFW
1 stop22h 39mFrontier
Deal found 10/20$104
This Mytrip deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/136:16 pmDFW - MDW
Nonstop2h 28mFrontier
ven. 11/146:29 pmMDW - DFW
Nonstop2h 35mFrontier
Deal found 10/18$105
This Frontier deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/259:01 pmDFW - MDW
Nonstop2h 19mFrontier
lun. 10/279:45 amMDW - DFW
1 stop9h 16mFrontier
Deal found 10/18$106
This Frontier deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/317:00 amDFW - MDW
Nonstop2h 21mFrontier
sam. 1/39:15 amMDW - DFW
Nonstop2h 50mFrontier
Deal found 10/18$107
This Priceline deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/306:15 pmDFW - MDW
Nonstop2h 28mFrontier
jeu. 11/69:34 pmMDW - DFW
Nonstop2h 38mFrontier
Deal found 10/19$108
This Frontier deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/102:57 pmDFW - MDW
Nonstop2h 18mFrontier
jeu. 11/139:39 pmMDW - DFW
Nonstop2h 38mFrontier
Deal found 10/19$109
This Frontier deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/2110:48 pmDFW - MDW
Nonstop2h 17mFrontier
ven. 11/285:05 amMDW - DFW
Nonstop2h 45mFrontier
Deal found 10/20$110
This Frontier deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/82:54 pmDFW - MDW
1 stop6h 41mFrontier
dim. 11/911:23 amMDW - DFW
Nonstop2h 35mFrontier
Deal found 10/18$111
This Frontier deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/136:16 pmDFW - MDW
Nonstop2h 28mFrontier
dim. 11/161:37 pmMDW - DFW
1 stop8h 36mFrontier
Deal found 10/18$112
This Frontier deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/136:16 pmDFW - MDW
Nonstop2h 28mFrontier
jeu. 11/209:30 amMDW - DFW
1 stop8h 40mFrontier
Deal found 10/18$113
This CheapOair deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/152:54 pmDFW - MDW
1 stop6h 41mFrontier
lun. 11/175:56 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 10/18$114

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dallas to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octobre 20, 2025.
Use the filters below to find and compare flights from Dallas to Chicago Midway Airport that are best for you.

Fly from

Dallas

Fly to

Midway

Route

Depart

Return

Price

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

dim. 1/18

7:00 am-9:10 am

Nonstop2h 10m

Chicago Midway

lun. 1/19

5:20 am-7:55 am

Nonstop2h 35m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mer. 11/12

6:45 am-8:55 am

Nonstop2h 10m

Chicago Midway

mar. 11/18

8:30 pm-10:55 pm

Nonstop2h 25m

$168

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

ven. 12/12

7:20 am-9:35 am

Nonstop2h 15m

Chicago Midway

lun. 12/15

1:20 pm-3:45 pm

Nonstop2h 25m

$174

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mar. 11/18

10:11 am-4:38 pm

1 stop6h 27m

Chicago Midway

jeu. 11/27

5:34 pm-11:52 pm

1 stop6h 18m

$177

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

sam. 2/21

10:20 am-3:25 pm

1 stop5h 05m

Chicago Midway

mar. 2/24

6:00 am-1:20 pm

1 stop7h 20m

$177

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mar. 2/3

2:00 pm-9:46 pm

1 stop7h 46m

Chicago Midway

mer. 2/11

5:25 pm-10:36 pm

1 stop5h 11m

$177

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

mer. 11/19

7:01 am-11:52 am

1 stop4h 51m

Chicago Midway

jeu. 11/27

9:34 am-2:18 pm

1 stop4h 44m

$177

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

mar. 11/18

11:31 am-4:38 pm

1 stop5h 07m

Chicago Midway

jeu. 11/27

9:34 am-2:18 pm

1 stop4h 44m

$177

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

jeu. 12/4

3:35 pm-7:30 pm

1 stop3h 55m

Chicago Midway

dim. 12/7

7:40 am-10:05 am

Nonstop2h 25m

$188

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

mar. 11/11

4:04 pm-11:40 pm

1 stop7h 36m

Chicago Midway

mar. 11/18

9:34 am-2:18 pm

1 stop4h 44m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 42 results
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Best time to book a flight from Dallas to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Dallas with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Dallas to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Dallas to Midway. Price data was last updated on October 17, 2025.

Booking 86 days in advance of your planned departure date is, on average, the best time to get cheap flights from Dallas to Chicago Midway Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Dallas to Chicago Midway Airport?

Currently, March is the cheapest month in which you can book a flight from Dallas to Chicago Midway Airport (average of $49). Flying from Dallas to Chicago Midway Airport in April is currently the most expensive (average of $145). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DFW to MDW?

Find hourly flight availability from Dallas to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octobre 20, 2025.

When flying from Dallas to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 16% versus a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Dallas to Midway. Price data was last updated on October 12, 2025.

Travelers seeking maximum savings on their Dallas to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Wednesday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Dallas to Chicago Midway Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-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.
Cheapflights partnered with top experts to bring you the best recommendations for your Dallas to Chicago Midway Airport trip
Airlines
Frontier

Frontier's UpFront Plus seats offer a guaranteed empty middle seat for extra comfort.


Frontier offers Zone 1 boarding with a carry-on purchase or special fare bundle.

Read more about Frontierby Marisa Garcia
Southwest

Southwest offers free messaging and high-speed Wi-Fi for a fee on flights.


Southwest's Early Bird check-in gives priority boarding 36 hours before departure.

Read more about Southwestby Marisa Garcia
Airports
DFW

DFW offers a DART Orange Line connecting downtown Dallas to Terminal A, making public transit a viable option for reaching the airport.

Read more about DFWby Chris Dong
MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and cost-effective travel option.

Read more about MDWby Ramsey Qubein
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Chris Dong

Chris Dong

Expert on DFW

Chris Dong

Chris Dong

Chris is a consumer travel reporter covering aviation, trending travel news, hotels, and loyalty programs—all for leading global publications like Travel + Leisure, The Washington Post, AFAR, and more. In addition to writing, Chris is a video host for Travel + Leisure, giving consumers an inside look at the latest in air travel.

Read more

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated octobre 20, 2025.
See what other customers who have flown with Southwest and Frontier from Dallas to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
5.8
Fair
3,130 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Dallas to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Dallas to Chicago Midway Airport?

    A quick flight from Dallas to Chicago Midway Airport can take about 2h 10m. Southwest provides one of the quickest options available for as low as $117. Dallas and Chicago Midway Airport are separated by a distance of 793 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Dallas to Chicago Midway Airport round-trip?

    According to our current data, Frontier ($77), and Southwest ($147) offers the cheapest pricing from Dallas to Chicago Midway Airport. Users have found that Frontier is 61% cheaper than the other options available to this destination.

  • What are the cheapest flights from Dallas to Chicago Midway Airport?

    While on average a flight from Dallas to Chicago Midway Airport is generally $166, our data shows the cheapest flight currently is $43. When looking at the most popular route, (Dallas/Fort Worth - Chicago Midway), you can expect to pay $54 for that flight.

  • Can I find deals for flights from Dallas to Midway that include hotel bookings?

    Yes. In addition to deals on Dallas to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dallas to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dallas to Midway.

  • Can I find deals for business class flights from Dallas to Midway?

    Yes. Cheapflights offers flight deals from Dallas to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, March is the cheapest month in which you can book a flight from Dallas to Chicago Midway Airport (average of $49). Flying from Dallas to Chicago Midway Airport in April is currently the most expensive (average of $145). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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Alternative routes for Dallas to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Dallas to Midway

Discover the top 2 airlines that operate flights from Dallas to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated octobre 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$181FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$296FlexibilityNo cancel feeOn-time63%

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