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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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

November

Cheapest in

April

Average price

$303

Good round-trip deal

$199 or less

Good one-way deal

$170 or less
From Dallas Love Field to Chicago Midway
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One-way flight from Dallas Love Field to Chicago Midway
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Highest demand for flights based on searches. 8% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Dallas Love Field to Chicago Midway.
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Price to beat on a one-way flight from Dallas Love Field to Chicago Midway.
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Find 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 September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:55 pmDAL - MDW
Nonstop2h 10mSouthwest
Mon 10/275:25 amMDW - DAL
Nonstop2h 15mSouthwest
Deal found 9/15$157
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:25 amDAL - MDW
Nonstop2h 10mSouthwest
Sat 10/2512:55 pmMDW - DAL
1 stop4h 05mSouthwest
Deal found 9/15$163
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:35 pmDAL - MDW
1 stop3h 55mSouthwest
Tue 12/93:20 pmMDW - DAL
1 stop3h 55mSouthwest
Deal found 9/16$168
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:40 pmDAL - MDW
Nonstop2h 10mSouthwest
Tue 11/188:25 amMDW - DAL
2 stops5h 10mSouthwest
Deal found 9/15$172
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/249:55 pmDAL - MDW
Nonstop2h 10mSouthwest
Wed 10/296:55 pmMDW - DAL
Nonstop2h 20mSouthwest
Deal found 9/15$177
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 pmDAL - MDW
Nonstop2h 15mSouthwest
Mon 11/31:55 pmMDW - DAL
1 stop4h 05mSouthwest
Deal found 9/14$178
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:35 pmDAL - MDW
1 stop5h 00mSouthwest
Sat 11/155:50 amMDW - DAL
2 stops6h 05mSouthwest
Deal found 9/14$182
This Southwest deal was found by Cheapflights users on 9/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/273:30 pmDAL - MDW
Nonstop2h 15mSouthwest
Fri 12/53:20 pmMDW - DAL
1 stop3h 55mSouthwest
Deal found 9/16$183
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:25 pmDAL - MDW
Nonstop2h 15mSouthwest
Mon 10/273:45 pmMDW - DAL
1 stop4h 25mSouthwest
Deal found 9/15$187
This Southwest deal was found by Cheapflights users on 9/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/106:55 pmDAL - MDW
1 stop5h 30mSouthwest
Sat 10/117:30 pmMDW - DAL
Nonstop2h 15mSouthwest
Deal found 9/14$189
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/199:00 amDAL - MDW
Nonstop2h 15mSouthwest
Sun 11/235:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 9/15$191

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 September 17, 2025.
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

Wed 10/29

10:25 am-12:40 pm

Nonstop2h 15m

Chicago Midway

Sat 11/1

7:30 pm-9:45 pm

Nonstop2h 15m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 10/22

9:55 pm-12:05 am

Nonstop2h 10m

Chicago Midway

Sat 10/25

5:45 am-8:00 am

Nonstop2h 15m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 12/8

5:10 pm-7:25 pm

Nonstop2h 15m

Chicago Midway

Tue 12/9

1:15 pm-3:40 pm

Nonstop2h 25m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 10/16

7:40 am-9:55 am

Nonstop2h 15m

Chicago Midway

Tue 10/21

8:25 pm-10:40 pm

Nonstop2h 15m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 11/6

6:00 am-8:15 am

Nonstop2h 15m

Chicago Midway

Mon 11/10

4:25 pm-6:50 pm

Nonstop2h 25m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 12/23

6:00 am-8:15 am

Nonstop2h 15m

Chicago Midway

Thu 12/25

5:00 am-7:30 am

Nonstop2h 30m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 11/12

10:30 am-12:40 pm

Nonstop2h 10m

Chicago Midway

Tue 11/18

3:20 pm-7:15 pm

1 stop3h 55m

$163

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 10/23

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Sat 10/25

12:55 pm-5:00 pm

1 stop4h 05m

$163

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 11/17

9:00 am-11:15 am

Nonstop2h 15m

Chicago Midway

Wed 11/19

5:35 am-9:55 am

1 stop4h 20m

$167

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 10/23

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Mon 10/27

3:45 pm-8:10 pm

1 stop4h 25m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 20 results
1
2

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 $160). Flying from Dallas Love Field 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 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 September 17, 2025.

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 31% 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 September 14, 2025.

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. 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 September 17, 2025.
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
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

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 $157, 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 $158. Southwest is 46% 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 $272, our data shows the cheapest flight currently is $71. 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 $160). Flying from Dallas Love Field 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

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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$307FlexibilityNo cancel feeOn-time63%

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