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$79+ Cheap flights from Love Field (DAL) 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap flight deals from Love Field to Midway

Cheapest flights from Love Field to Midway
Explore the most affordable flight options available from Love Field to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 21, 2026.

This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
DAL
-
MDW
Nonstop2h 10m
Southwest
Wed 3/258:35 pm
MDW
-
DAL
Nonstop2h 30m
Southwest
Deal found 2/18$157
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:00 am
DAL
-
MDW
Nonstop2h 10m
Southwest
Tue 3/248:35 pm
MDW
-
DAL
Nonstop2h 30m
Southwest
Deal found 2/20$158
This Southwest deal was found by Cheapflights users on 2/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:50 pm
DAL
-
MDW
Nonstop2h 15m
Southwest
Tue 4/2811:35 am
MDW
-
DAL
Nonstop2h 25m
Southwest
Deal found 2/19$163
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:15 am
DAL
-
MDW
Nonstop2h 10m
Southwest
Sun 4/265:00 am
MDW
-
DAL
Nonstop2h 25m
Southwest
Deal found 2/20$169
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:10 pm
DAL
-
MDW
Nonstop2h 15m
Southwest
Sat 5/23:05 pm
MDW
-
DAL
Nonstop2h 25m
Southwest
Deal found 2/20$172
This Southwest deal was found by Cheapflights users on 2/21. 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 4/159:40 am
DAL
-
MDW
Nonstop2h 15m
Southwest
Sat 4/1810:00 am
MDW
-
DAL
2 stops6h 00m
Southwest
Deal found 2/21$173
This Southwest deal was found by Cheapflights users on 2/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:15 am
DAL
-
MDW
Nonstop2h 10m
Southwest
Sat 4/116:15 pm
MDW
-
DAL
Nonstop2h 25m
Southwest
Deal found 2/18$174
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:15 am
DAL
-
MDW
Nonstop2h 10m
Southwest
Sun 5/35:00 am
MDW
-
DAL
Nonstop2h 25m
Southwest
Deal found 2/20$175
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:17 am
DAL
-
MDW
1 stop6h 09m
Delta
Tue 5/512:52 pm
MDW
-
DAL
1 stop4h 58m
Delta
Deal found 2/20$177

Find flight deals from Love Field to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Love Field (DAL) 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 February 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$154
(Southwest)

One-way from

$79
(Southwest)

Popular in

October

Cheapest in

December

Average price

$333

Good round-trip deal

$240 or less

Good one-way deal

$177 or less
Provider with most accurate pricing for Dallas Love Field-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Dallas Love Field-Chicago Midway flights.
Search Deals
From Dallas Love Field to Chicago Midway
Search Deals
One-way flight from Dallas Love Field to Chicago Midway
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a round-trip flight from Dallas Love Field to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Dallas Love Field to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Love Field 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 February 21, 2026.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago Midway Airport that are best for you.

Fly from

Love Field

Fly to

Midway

Route

Depart

Return

Price

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 4/14

1:10 pm-3:25 pm

Nonstop2h 15m

Chicago Midway

Tue 4/14

4:50 pm-10:00 pm

1 stop5h 10m

$167

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 4/28

1:10 pm-3:25 pm

Nonstop2h 15m

Chicago Midway

Sat 5/2

3:05 pm-5:30 pm

Nonstop2h 25m

$172

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 4/8

6:05 pm-8:20 pm

Nonstop2h 15m

Chicago Midway

Mon 4/13

5:30 am-7:55 am

Nonstop2h 25m

$174

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 4/16

6:20 am-8:30 am

Nonstop2h 10m

Chicago Midway

Mon 4/20

5:30 am-7:55 am

Nonstop2h 25m

$181

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 3/20

7:50 pm-10:00 pm

Nonstop2h 10m

Chicago Midway

Tue 3/24

10:30 am-3:15 pm

1 stop4h 45m

$184

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 3/25

7:10 pm-9:20 pm

Nonstop2h 10m

Chicago Midway

Mon 3/30

6:10 pm-10:55 pm

1 stop4h 45m

$184

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 4/25

6:50 pm-9:05 pm

Nonstop2h 15m

Chicago Midway

Mon 4/27

4:00 pm-8:55 pm

1 stop4h 55m

$184

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 4/18

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Sat 4/18

10:00 am-4:00 pm

2 stops6h 00m

$189

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 4/8

1:05 pm-5:05 pm

1 stop4h 00m

Chicago Midway

Sat 4/11

2:15 pm-8:15 pm

1 stop6h 00m

$194

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 4/25

6:15 am-12:10 pm

2 stops5h 55m

Chicago Midway

Tue 4/28

4:50 pm-10:00 pm

1 stop5h 10m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Love Field 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 Love Field to Midway in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 Love Field Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Dallas Love Field Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Dallas Love Field Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Dallas Love Field Airport-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub 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 Love Field 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 Love Field to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Love Field 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 Love Field Airport to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago Midway Airport (average of $147). Flying from Dallas Love Field Airport to Chicago Midway Airport in January is currently the most expensive (average of $278). 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 DAL to MDW?

Find hourly flight availability from Love Field 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 February 21, 2026.

One of the essential ways to save on airfare from Dallas Love Field Airport to Chicago Midway Airport is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 21% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Love Field to Midway. Price data was last updated on February 21, 2026.

Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago Midway Airport flight should consider departing on Saturday afternoons when fares are most often at their lowest. Monday 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 February 21, 2026.
Get a feel of what it's like to fly with Southwest from Dallas Love Field Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,298 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
4,298 reviews
Southwest
8.0
Very good
4,298 reviews

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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 Love Field 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 Love Field Airport to Chicago Midway Airport?

    For as low as $167, Southwest can have you in Chicago Midway Airport from Dallas Love Field Airport in 2h 15m. The distance from Dallas Love Field Airport to Chicago Midway Airport is about 793 mi. Most flights are nonstop.

  • What is the cheapest airline to fly from Dallas Love Field Airport to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Dallas Love Field Airport to Chicago Midway Airport round-trip from $157. Southwest is 47% cheaper than the average price of flights available within the next 90 days to this destination.

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

    While on average a flight from Dallas Love Field Airport to Chicago Midway Airport is generally $261, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Dallas Love Field - Chicago Midway), you can expect to pay $157 for that flight.

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

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

  • How can I find direct flights from Love Field to Midway?

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

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

    Yes. Cheapflights offers flight deals from Love Field 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 Love Field Airport to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago Midway Airport (average of $147). Flying from Dallas Love Field Airport to Chicago Midway Airport in January is currently the most expensive (average of $278). 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
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Love Field 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
Dallas/Fort Worth to Midway flights
Love Field to O'Hare Intl flights

Top airline flying from Love Field to Midway

Discover the top airline that operate flights from Love Field 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 February 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$157Average$299FlexibilityNo cancel feeOn-time63%

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