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Midway

$67+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
DFW — MDW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
1 adult, Economy
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Cheapflights Tip: The best prices from Dallas/Fort Worth to Chicago Midway are usually found in September or October, booked 89 days in advance, depart on a Saturday or Wednesday and return on a Wednesday

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 August 18, 2025.

Round-trip from

$111
(CheapOair)

One-way from

$67
(SmartFares)

Popular in

May

Cheapest in

September

Average price

$198

Good round-trip deal

$113 or less

Good one-way deal

$114 or less
From Dallas/Fort Worth to Chicago Midway
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One-way flight from Dallas/Fort Worth to Chicago Midway
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Highest demand for flights based on searches. 12% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Dallas/Fort Worth to Chicago Midway.
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Price to beat on a one-way flight from Dallas/Fort Worth to Chicago Midway.
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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 August 18, 2025.

This CheapOair deal was found by Cheapflights users on 8/18. 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.
Fri 9/126:28 pmDFW - MDW
Nonstop2h 24mFrontier
Mon 9/159:47 pmMDW - DFW
Nonstop2h 34mFrontier
Deal found 8/18$111
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:55 amDFW - MDW
Nonstop2h 23mFrontier
Thu 9/1110:13 amMDW - DFW
Nonstop2h 38mFrontier
Deal found 8/18$112
This CheapOair deal was found by Cheapflights users on 8/17. 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 10/88:00 amDFW - MDW
1 stop5h 38mFrontier
Tue 10/145:20 pmMDW - DFW
Nonstop2h 41mFrontier
Deal found 8/17$114
This Cheapflightsfares deal was found by Cheapflights users on 8/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:45 pmDFW - MDW
1 stop5h 35mFrontier
Mon 9/87:15 amMDW - DFW
Nonstop2h 31mFrontier
Deal found 8/16$115
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:28 pmDFW - MDW
Nonstop2h 24mFrontier
Mon 9/89:47 pmMDW - DFW
Nonstop2h 34mFrontier
Deal found 8/17$117
This Frontier deal was found by Cheapflights users on 8/18. 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.
Fri 9/55:45 amDFW - MDW
1 stop10h 15mFrontier
Fri 9/127:15 amMDW - DFW
Nonstop2h 31mFrontier
Deal found 8/18$118
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:01 pmDFW - MDW
Nonstop2h 19mFrontier
Mon 10/206:24 pmMDW - DFW
1 stop6h 00mFrontier
Deal found 8/18$119
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:00 amDFW - MDW
Nonstop2h 28mFrontier
Mon 9/229:47 pmMDW - DFW
Nonstop2h 34mFrontier
Deal found 8/17$121
This Gotogate deal was found by Cheapflights users on 8/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/48:00 amDFW - MDW
Nonstop2h 28mFrontier
Mon 10/66:21 amMDW - DFW
1 stop8h 27mFrontier
Deal found 8/16$122
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1510:41 amDFW - MDW
Nonstop2h 30mFrontier
Thu 9/1810:13 amMDW - DFW
Nonstop2h 38mFrontier
Deal found 8/17$123
This Frontier deal was found by Cheapflights users on 8/17. 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.
Fri 10/109:01 pmDFW - MDW
Nonstop2h 19mFrontier
Sun 10/1212:44 pmMDW - DFW
1 stop11h 34mFrontier
Deal found 8/17$124

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 August 18, 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

Wed 10/8

8:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Tue 10/14

5:20 pm-8:01 pm

Nonstop2h 41m

$114

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 10/31

2:57 pm-5:15 pm

Nonstop2h 18m

Chicago Midway

Mon 11/3

1:37 pm-8:00 pm

1 stop6h 23m

$115

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/25

5:45 pm-11:20 pm

1 stop5h 35m

Chicago Midway

Fri 10/3

9:47 pm-12:21 am

Nonstop2h 34m

$115

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Mon 11/3

2:57 pm-5:15 pm

Nonstop2h 18m

Chicago Midway

Thu 11/6

1:37 pm-8:00 pm

1 stop6h 23m

$115

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 10/22

8:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Sat 10/25

5:20 pm-8:01 pm

Nonstop2h 41m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Fri 11/14

2:57 pm-5:15 pm

Nonstop2h 18m

Chicago Midway

Mon 11/17

1:37 pm-8:00 pm

1 stop6h 23m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 10/22

8:00 am-1:38 pm

1 stop5h 38m

Chicago Midway

Fri 10/24

5:10 am-7:45 am

Nonstop2h 35m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/11

5:45 pm-11:20 pm

1 stop5h 35m

Chicago Midway

Mon 9/15

9:47 pm-12:21 am

Nonstop2h 34m

$116

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Tue 10/21

9:01 pm-11:20 pm

Nonstop2h 19m

$67

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Thu 9/11

6:55 am-9:18 am

Nonstop2h 23m

$68

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 15 results
1
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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

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 August 8, 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 88 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, April is the cheapest month in which you can book a flight from Dallas/Fort Worth Airport to Chicago Midway Airport (average of $160). Flying from Dallas/Fort Worth Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 August 18, 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 10% 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 August 17, 2025.

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

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 August 18, 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
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

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
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

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 5h 38m. The distance from Dallas/Fort Worth Airport to Chicago Midway Airport is about 797 mi.

  • 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 $69. Another option worth looking into is Southwest, starting at $147 round trip. Frontier is currently priced 65% 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 $79. On average you can expect to pay $178. The most popular route, (Dallas/Fort Worth - Chicago Midway), can usually be booked for $114.

  • 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, April is the cheapest month in which you can book a flight from Dallas/Fort Worth Airport to Chicago Midway Airport (average of $160). Flying from Dallas/Fort Worth Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$69Average$175FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$295FlexibilityNo cancel feeOn-time63%

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