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Midway

$44+ Cheap flights from Dallas/Fort Worth (DFW) 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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
DFW — MDW
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
1 adult, Economy
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Find cheap flights from Dallas/Fort Worth to Midway with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Dallas/Fort Worth 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

Find flight deals from Dallas/Fort Worth to Midway

Cheapest flights from Dallas/Fort Worth to Midway
Explore the most affordable flight options available from Dallas/Fort Worth to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 16, 2025.

This CheapOair deal was found by Cheapflights users on 11/15. 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.
Sat 12/66:00 amDFW - MDW
1 stop7h 59mFrontier
Sun 12/148:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/15$88
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/249:54 pmDFW - MDW
Nonstop2h 19mFrontier
Thu 11/276:15 pmMDW - DFW
Nonstop2h 44mFrontier
Deal found 11/14$89
This Super.com deal was found by Cheapflights users on 11/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:10 pmDFW - MDW
Nonstop2h 18mFrontier
Tue 12/238:00 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/15$91
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:54 pmDFW - MDW
Nonstop2h 19mFrontier
Mon 11/245:30 amMDW - DFW
Nonstop2h 45mFrontier
Deal found 11/15$93
This CheapOair deal was found by Cheapflights users on 11/16. 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.
Wed 12/247:00 amDFW - MDW
Nonstop2h 21mFrontier
Sun 1/410:50 pmMDW - DFW
1 stop25h 19mFrontier
Deal found 11/16$94
This Frontier deal was found by Cheapflights users on 11/16. 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.
Thu 12/46:05 amDFW - MDW
1 stop12h 03mFrontier
Mon 12/812:35 pmMDW - DFW
Nonstop2h 30mFrontier
Deal found 11/16$95
This Super.com deal was found by Cheapflights users on 11/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:00 amDFW - MDW
Nonstop2h 21mFrontier
Wed 12/318:15 amMDW - DFW
1 stop7h 29mFrontier
Deal found 11/15$96
This CheapOair deal was found by Cheapflights users on 11/16. 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.
Fri 12/1211:47 amDFW - MDW
Nonstop2h 17mFrontier
Sun 12/148:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/16$98
This CheapOair deal was found by Cheapflights users on 11/16. 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.
Tue 12/3011:42 amDFW - MDW
Nonstop2h 17mFrontier
Sat 1/37:05 amMDW - DFW
Nonstop2h 43mFrontier
Deal found 11/16$99
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/56:27 pmDFW - MDW
1 stop28h 03mFrontier
Fri 12/128:05 amMDW - DFW
Nonstop2h 42mFrontier
Deal found 11/14$101

Cheap flight deals from Dallas/Fort Worth to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Dallas/Fort Worth (DFW) 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 November 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$88
(CheapOair)

One-way from

$44
(CheapOair)

Popular in

May

Cheapest in

February

Average price

$229

Good round-trip deal

$123 or less

Good one-way deal

$86 or less
Provider with most accurate pricing for Dallas/Fort Worth-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Dallas/Fort Worth-Chicago Midway flights.
Search Deals
From Dallas/Fort Worth to Chicago Midway
Search Deals
One-way flight from Dallas/Fort Worth to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Dallas/Fort Worth to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Dallas/Fort Worth to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dallas/Fort Worth 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 November 16, 2025.
Use the filters below to find and compare flights from Dallas/Fort Worth Airport to Chicago Midway Airport that are best for you.

Fly from

Dallas/Fort Worth

Fly to

Midway

Route

Depart

Return

Price

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 12/1

9:54 pm-12:13 am

Nonstop2h 19m

Chicago Midway

Thu 12/4

8:05 am-10:47 am

Nonstop2h 42m

$110

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 12/5

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Sun 12/7

6:37 pm-7:41 am

1 stop13h 04m

$118

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sun 12/7

11:47 am-2:04 pm

Nonstop2h 17m

Chicago Midway

Mon 12/15

6:15 am-8:00 pm

1 stop13h 45m

$139

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 3/10

11:15 am-6:08 pm

1 stop6h 53m

Chicago Midway

Wed 3/11

1:05 pm-9:01 pm

1 stop7h 56m

$177

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Sat 12/13

11:47 am-6:06 pm

1 stop6h 19m

Chicago Midway

Mon 12/15

9:34 am-2:21 pm

1 stop4h 47m

$184

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 12/10

1:37 pm-6:00 pm

1 stop4h 23m

Chicago Midway

Tue 12/16

9:34 am-2:21 pm

1 stop4h 47m

$188

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 12/9

5:19 am-11:55 am

1 stop6h 36m

Chicago Midway

Tue 12/16

9:34 am-2:21 pm

1 stop4h 47m

$188

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 12/30

8:57 pm-9:58 pm

1 stop25h 01m

Chicago Midway

Sun 1/4

10:50 pm-12:09 am

1 stop25h 19m

$195

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 12/15

5:19 am-11:55 am

1 stop6h 36m

Chicago Midway

Wed 12/17

6:00 am-1:13 pm

1 stop7h 13m

$197

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 12/31

6:00 am-1:21 pm

1 stop7h 21m

Chicago Midway

Sat 1/3

8:15 am-4:48 pm

1 stop8h 33m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

Showing 1-10 of 21 results
1
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3

Compare providers for flights from Dallas/Fort Worth to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Dallas/Fort Worth to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
CheapOairPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Dallas/Fort Worth Airport-Chicago Midway Airport flights, users find the pricing of CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Dallas/Fort Worth Airport-Chicago Midway Airport flight deals on Cheapflights vs. CheapOair >95% of the time. Price accuracy is based on data collected from Dallas/Fort Worth Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Dallas/Fort Worth Airport-Chicago Midway Airport flights, Cheapflights users trust CheapOair the most. CheapOair has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Dallas/Fort Worth Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Dallas/Fort Worth to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Dallas/Fort Worth 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/Fort Worth Airport to Chicago Midway Airport

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

Use this chart to determine the optimal time to book a round-trip flight from Dallas/Fort Worth to Midway. Price data was last updated on November 7, 2025.

The price you pay for your flight from Dallas/Fort Worth Airport to Chicago Midway Airport may vary depending on when you book. For the best chance of a lower fare, look to book 86 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, March is the cheapest month in which you can book a flight from Dallas/Fort Worth Airport to Chicago Midway Airport (average of $49). Flying from Dallas/Fort Worth Airport 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/Fort Worth 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 November 16, 2025.

When flying from Dallas/Fort Worth Airport to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 13% versus a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Dallas/Fort Worth to Midway. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Dallas/Fort Worth Airport 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/Fort Worth Airport 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/Fort Worth Airport to Chicago Midway Airport trip
Airports
DFW

DFW offers a DART Orange Line connecting downtown Dallas to the airport, with a station at Terminal A for easy access.

Read more about DFWby Chris Dong
MDW

The Orange Line train provides a direct route from MDW to downtown Chicago in under 30 minutes, making it a convenient option.

Read more about MDWby Ramsey Qubein
Our travel experts
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 November 16, 2025.
Read reviews from past customers who have flown Southwest and Frontier from Dallas/Fort Worth Airport to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

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
3,109 reviews
Southwest
8.0
Very good
4,245 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

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/Fort Worth 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/Fort Worth Airport to Chicago Midway Airport?

    Departing from Dallas/Fort Worth Airport to Chicago Midway Airport will take you 2h 19m. The distance from Dallas/Fort Worth Airport to Chicago Midway Airport is about 797 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $76. Another option worth looking into is Southwest, starting at $147 round trip. Frontier is currently priced 62% below the average price you’ll pay for this route.

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

    The cheapest flight price from Dallas/Fort Worth Airport to Chicago Midway Airport is $30. On average you can expect to pay $159. The most popular route, (Dallas/Fort Worth - Chicago Midway), can usually be booked for $82.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Dallas/Fort Worth 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/Fort Worth Airport to Chicago Midway Airport?

    Currently, March is the cheapest month in which you can book a flight from Dallas/Fort Worth Airport to Chicago Midway Airport (average of $49). Flying from Dallas/Fort Worth Airport 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Dallas/Fort Worth to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Love Field to O'Hare Intl flights
Love Field to Midway flights

Top 2 airlines flying from Dallas/Fort Worth to Midway

Discover the top 2 airlines that operate flights from Dallas/Fort Worth 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 November 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$181FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$285FlexibilityNo cancel feeOn-time63%

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