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Midway

$72+ 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 7/11. Fares are subject to change and may not be available on all flights or dates of travel.
DFW — MDW
Jun 25 — Jul 21
Thu 6/25
Thu 7/2
1 adult, Economy
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Cheapflights Tip: The best prices from Dallas to Chicago Midway are usually found in December or January, booked 49 days in advance, depart on a Sunday or Saturday and return on a Tuesday

Cheap 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 May 26, 2026.

This Frontier deal was found by Cheapflights users on 5/25. 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.
Sat 7/113:01 pm
DFW
-
MDW
Nonstop2h 25m
Frontier
Sat 7/186:41 pm
MDW
-
DFW
Nonstop2h 40m
Frontier
Deal found 5/25$168
This Super.com deal was found by Cheapflights users on 5/24. 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 7/412:49 pm
DFW
-
MDW
Nonstop2h 26m
Frontier
Sat 7/116:41 pm
MDW
-
DFW
Nonstop2h 40m
Frontier
Deal found 5/24$186
This Gotogate deal was found by Cheapflights users on 5/25. 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.
Thu 7/96:08 pm
DFW
-
MDW
Nonstop2h 24m
Frontier
Thu 7/169:27 pm
MDW
-
DFW
Nonstop2h 32m
Frontier
Deal found 5/25$189
This Kiwi.com deal was found by Cheapflights users on 5/25. 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.
Sat 6/2712:49 pm
DFW
-
MDW
Nonstop2h 26m
Frontier
Sat 7/44:10 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/25$190
This Super.com deal was found by Cheapflights users on 5/23. 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 5/2711:55 am
DFW
-
MDW
Nonstop2h 17m
Frontier
Fri 5/293:07 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/23$191
This Kiwi.com deal was found by Cheapflights users on 5/22. 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.
Sat 7/113:01 pm
DFW
-
MDW
Nonstop2h 25m
Frontier
Thu 7/169:27 pm
MDW
-
DFW
Nonstop2h 32m
Frontier
Deal found 5/22$192
This Kiwi.com deal was found by Cheapflights users on 5/23. 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.
Wed 5/2711:55 am
DFW
-
MDW
Nonstop2h 17m
Frontier
Thu 5/283:07 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/23$195
This Frontier deal was found by Cheapflights users on 5/23. 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.
Mon 5/2511:55 am
DFW
-
MDW
Nonstop2h 17m
Frontier
Thu 5/283:07 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/23$196
This Super.com deal was found by Cheapflights users on 5/23. 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 6/2012:49 pm
DFW
-
MDW
Nonstop2h 26m
Frontier
Sat 6/274:10 pm
MDW
-
DFW
Nonstop2h 43m
Frontier
Deal found 5/23$197
This Southwest deal was found by Cheapflights users on 5/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/44:40 pm
DAL
-
MDW
Nonstop2h 15m
Southwest
Wed 7/88:55 pm
MDW
-
DAL
Nonstop2h 20m
Southwest
Deal found 5/24$281
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/284:30 pm
DAL
-
MDW
1 stop4h 15m
Southwest
Sat 8/16:30 am
MDW
-
DAL
Nonstop2h 20m
Southwest
Deal found 5/26$287
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:40 am
DAL
-
MDW
1 stop5h 10m
Southwest
Tue 6/306:30 am
MDW
-
DAL
Nonstop2h 20m
Southwest
Deal found 5/26$291

Find 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 May 26, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$168
(Frontier)

One-way from

$72
(iWofly)

Popular in

May

Cheapest in

December

Average price

$284
Provider with most accurate pricing for Dallas-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Dallas-Chicago (CHI) flights.
Search Deals
From Dallas to Chicago Midway
Search Deals
One-way flight from Dallas to Chicago Midway
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 26, 2026.
Use the filters below to find and compare flights from Dallas to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 6/13

6:45 pm-9:00 pm

Nonstop2h 15m

Chicago Midway

Sat 6/20

6:30 am-8:50 am

Nonstop2h 20m

$281

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 6/13

6:00 am-8:15 am

Nonstop2h 15m

Chicago Midway

Sat 6/13

8:55 pm-11:10 pm

Nonstop2h 15m

$281

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 7/15

11:16 am-6:18 pm

1 stop7h 02m

Chicago Midway

Sat 7/18

10:55 am-5:32 pm

1 stop6h 37m

$301

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 8/5

7:00 am-1:08 pm

1 stop6h 08m

Chicago Midway

Sat 8/8

10:56 am-3:51 pm

1 stop4h 55m

$301
Quickest round-trip

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 8/19

9:50 am-12:00 pm

Nonstop2h 10m

Chicago Midway

Sun 8/23

6:05 am-8:15 am

Nonstop2h 10m

$308

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 7/1

10:55 am-6:31 pm

2 stops7h 36m

Chicago Midway

Tue 7/7

1:49 pm-12:18 am

2 stops10h 29m

$311

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 7/1

9:55 pm-12:05 am

Nonstop2h 10m

Chicago Midway

Tue 7/7

5:05 am-7:20 am

Nonstop2h 15m

$312

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 7/29

8:00 am-12:10 pm

1 stop4h 10m

Chicago Midway

Fri 7/31

11:00 am-1:15 pm

Nonstop2h 15m

$314

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 8/6

1:20 pm-4:55 pm

1 stop3h 35m

Chicago Midway

Sat 8/8

6:45 am-8:55 am

Nonstop2h 10m

$314

DallasChicago

DFW - MDW

DFWMDW

Dallas/Fort Worth

Wed 7/15

5:05 pm-10:15 pm

1 stop5h 10m

Chicago Midway

Mon 7/20

9:19 am-2:32 pm

1 stop5h 13m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/24

Showing 1-10 of 42 resultsSorted by cheapest first
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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

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

Currently, October is the cheapest month in which you can book a flight from Dallas to Chicago Midway Airport (average of $39). Flying from Dallas to Chicago Midway Airport in July is currently the most expensive (average of $111). 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 May 26, 2026.

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 14% versus a flight in the afternoon.

Weekly flight availability from Dallas to Chicago Midway Airport

Explore weekly flight availability from Dallas to Midway. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 26, 2026.

The most flights from A78 to MDW are scheduled on a Monday (2 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

How much does it cost to fly round-trip from Dallas to Chicago Midway Airport?

How often are flights from Dallas to Chicago delayed?

About 23% of weekly flights between Dallas and Chicago have experienced delays in the past year, with the average delay time being 155 minutes.

What is the most punctual flight time for Dallas to Chicago flights?

Historically, flights departing in the early afternoon are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Friday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Dallas to Chicago flights?

Over the last year, Frontier have had the lowest number of delays on this route, with just 23% of flights being delayed.

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

Booking 48 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 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 May 23, 2026.

Travelers seeking maximum savings on their Dallas to Chicago Midway Airport flight should consider departing on Saturday evenings 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.

The best insider tips for Dallas to Chicago Midway Airport flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Dallas to Chicago Midway Airport trip
Our travel experts
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

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

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 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 May 26, 2026.
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
7.9
Good
4,265 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
7.9
Good
4,265 reviews
Southwest
7.9
Good
4,265 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.6
Fair
2,932 reviews
Southwest
7.9
Good
4,265 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

7.9

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 15m. Southwest provides one of the quickest options available for as low as $281. 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 63% 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 $178, our data shows the cheapest flight currently is $46. When looking at the most popular route, (Dallas/Fort Worth - Chicago Midway), you can expect to pay $76 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, October is the cheapest month in which you can book a flight from Dallas to Chicago Midway Airport (average of $39). Flying from Dallas to Chicago Midway Airport in July is currently the most expensive (average of $111). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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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 May 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$77Average$187FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$147Average$332FlexibilityNo cancel feeOn-time63%

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