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$59+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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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 November 25, 2025.

This Southwest deal was found by Cheapflights users on 11/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:40 pmDAL - MDW
Nonstop2h 10mSouthwest
Thu 1/15:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 11/25$117
This Southwest deal was found by Cheapflights users on 11/24. 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.
Wed 12/243:35 pmDAL - MDW
1 stop3h 55mSouthwest
Thu 1/15:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 11/24$123
This Southwest deal was found by Cheapflights users on 11/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:45 amDAL - MDW
Nonstop2h 10mSouthwest
Wed 12/318:15 amMDW - DAL
1 stop4h 50mSouthwest
Deal found 11/23$127
This Southwest deal was found by Cheapflights users on 11/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:35 pmDAL - MDW
1 stop3h 55mSouthwest
Wed 12/315:35 amMDW - DAL
1 stop4h 20mSouthwest
Deal found 11/23$132
This Southwest deal was found by Cheapflights users on 11/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:30 amDAL - MDW
1 stop3h 35mSouthwest
Thu 12/2510:00 amMDW - DAL
1 stop4h 25mSouthwest
Deal found 11/23$152
This Southwest deal was found by Cheapflights users on 11/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:50 pmDAL - MDW
Nonstop2h 10mSouthwest
Wed 12/175:35 pmMDW - DAL
Nonstop2h 25mSouthwest
Deal found 11/23$164
This Southwest deal was found by Cheapflights users on 11/23. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/298:40 pmDAL - MDW
Nonstop2h 10mSouthwest
Thu 1/15:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 11/23$171
This Southwest deal was found by Cheapflights users on 11/24. 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.
Tue 12/163:35 pmDAL - MDW
1 stop3h 55mSouthwest
Wed 12/175:35 amMDW - DAL
1 stop4h 20mSouthwest
Deal found 11/24$172
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/166:37 pmDAL - MDW
1 stop5h 10mDelta
Wed 12/175:29 pmMDW - DAL
1 stop6h 27mDelta
Deal found 11/24$177

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 November 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

October

Cheapest in

April

Average price

$314

Good round-trip deal

$202 or less

Good one-way deal

$178 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.
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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. 13% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 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 Love Field to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Dallas Love Field to Chicago Midway.
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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 November 25, 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

Thu 1/8

6:30 pm-8:40 pm

Nonstop2h 10m

Chicago Midway

Fri 1/9

8:00 pm-10:25 pm

Nonstop2h 25m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 1/12

7:00 am-9:10 am

Nonstop2h 10m

Chicago Midway

Thu 1/15

8:30 pm-10:55 pm

Nonstop2h 25m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sun 1/11

7:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Thu 1/15

5:20 am-7:55 am

Nonstop2h 35m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 1/15

6:35 am-8:45 am

Nonstop2h 10m

Chicago Midway

Sun 1/18

1:30 pm-7:00 pm

1 stop5h 30m

$123

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 12/24

3:35 pm-7:30 pm

1 stop3h 55m

Chicago Midway

Wed 12/31

5:35 am-9:55 am

1 stop4h 20m

$132

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 1/9

4:50 pm-7:00 pm

Nonstop2h 10m

Chicago Midway

Sat 1/10

11:00 am-4:50 pm

1 stop5h 50m

$140

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 1/8

1:45 pm-7:05 pm

2 stops5h 20m

Chicago Midway

Mon 1/12

8:00 pm-10:25 pm

Nonstop2h 25m

$145

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 1/23

6:30 pm-8:40 pm

Nonstop2h 10m

Chicago Midway

Sun 1/25

5:55 am-12:10 pm

1 stop6h 15m

$162

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 12/31

4:55 pm-10:22 pm

1 stop5h 27m

Chicago Midway

Tue 1/13

11:21 am-5:47 pm

1 stop6h 26m

$177

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 12/16

6:37 pm-11:47 pm

1 stop5h 10m

Chicago Midway

Wed 12/17

5:29 pm-11:56 pm

1 stop6h 27m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/23

Showing 1-10 of 21 results
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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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
OvagoPrice Accuracy2 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust 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 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 Expedia the most. Expedia 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 June is currently the most expensive (average of $247). 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 November 25, 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 28% 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 November 2, 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 November 25, 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
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

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
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

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 $117, Southwest can have you in Chicago Midway Airport from Dallas Love Field Airport in 2h 10m. 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 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 $274, our data shows the cheapest flight currently is $89. When looking at the most popular route, (Dallas Love Field - Chicago Midway), you can expect to pay $117 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 June is currently the most expensive (average of $247). 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

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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 November 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$305FlexibilityNo cancel feeOn-time63%

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