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Love Field

$74+ Cheap flights from Midway (MDW) to Love Field (DAL)

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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DAL
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Midway to Love Field

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Love Field (DAL). 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 15, 2025.

Round-trip from

$137
(Southwest)

One-way from

$74
(Southwest)

Popular in

March

Cheapest in

April

Average price

$258

Good round-trip deal

$187 or less

Good one-way deal

$178 or less
From Chicago Midway to Dallas Love Field
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One-way flight from Chicago Midway to Dallas Love Field
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Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 Chicago Midway to Dallas Love Field.
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Price to beat on a one-way flight from Chicago Midway to Dallas Love Field.
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Find flight deals from Midway to Love Field

Cheapest flights from Midway to Love Field
Explore the most affordable flight options available from Midway to Love Field. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 10/225:30 amMDW - DAL
Nonstop2h 15mSouthwest
Sat 10/253:45 pmDAL - MDW
1 stop4h 35mSouthwest
Deal found 9/12$137
This Southwest deal was found by Cheapflights users on 9/12. 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 10/255:45 amMDW - DAL
Nonstop2h 15mSouthwest
Mon 10/279:55 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 9/12$142
This Southwest deal was found by Cheapflights users on 9/13. 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 10/295:30 amMDW - DAL
Nonstop2h 15mSouthwest
Sun 11/25:00 amDAL - MDW
Nonstop2h 15mSouthwest
Deal found 9/13$146
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.
Sat 10/252:15 pmMDW - DAL
Nonstop2h 15mSouthwest
Sat 10/256:05 pmDAL - MDW
Nonstop2h 15mSouthwest
Deal found 9/15$157
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.
Thu 10/165:25 amMDW - DAL
Nonstop2h 15mSouthwest
Sat 10/184:40 pmDAL - MDW
1 stop5h 45mSouthwest
Deal found 9/14$167
This Southwest deal was found by Cheapflights users on 9/13. 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 10/315:35 amMDW - DAL
Nonstop2h 15mSouthwest
Wed 11/56:40 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 9/13$168

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Love Field 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 15, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Dallas Love Field Airport that are best for you.

Fly from

Midway

Fly to

Love Field

Route

Depart

Return

Price

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/22

2:15 pm-7:10 pm

1 stop4h 55m

Dallas Love Field

Sat 10/25

5:55 pm-10:25 pm

1 stop4h 30m

$147

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/29

12:35 pm-6:00 pm

1 stop5h 25m

Dallas Love Field

Sun 11/2

5:00 am-7:15 am

Nonstop2h 15m

$156

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 11/12

8:30 pm-10:55 pm

Nonstop2h 25m

Dallas Love Field

Tue 11/18

9:00 am-11:15 am

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 10/30

12:55 pm-3:10 pm

Nonstop2h 15m

Dallas Love Field

Mon 11/3

6:45 am-8:55 am

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 11/6

5:00 am-7:30 am

Nonstop2h 30m

Dallas Love Field

Mon 11/10

6:00 am-8:15 am

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 10/30

8:25 pm-10:40 pm

Nonstop2h 15m

Dallas Love Field

Sat 11/1

2:15 pm-4:30 pm

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Tue 10/7

8:25 pm-10:40 pm

Nonstop2h 15m

Dallas Love Field

Wed 10/8

9:55 pm-12:05 am

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/15

5:30 am-7:45 am

Nonstop2h 15m

Dallas Love Field

Wed 11/5

5:10 pm-7:25 pm

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 10/25

12:55 pm-5:00 pm

1 stop4h 05m

Dallas Love Field

Tue 10/28

2:55 pm-5:15 pm

Nonstop2h 20m

$163

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 10/25

12:55 pm-5:00 pm

1 stop4h 05m

Dallas Love Field

Mon 10/27

9:55 pm-12:05 am

Nonstop2h 10m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 19 results
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Best time to book a flight from Midway to Love Field

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Dallas Love Field Airport (average of $287). Flying from Chicago Midway Airport to Dallas Love Field Airport in March is currently the most expensive (average of $382). 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 MDW to DAL?

Find hourly flight availability from Midway to Love Field. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s optimal to fly from Chicago Midway Airport to Dallas Love Field Airport in the evening. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Love Field. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Dallas Love Field Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Love Field

Get insights into the airlines that provide service to Love Field. 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 Love Field. Reviews last updated September 15, 2025.
Peruse reviews from past customers who have flown with Southwest and Frontier from Chicago Midway Airport to Dallas Love Field Airport to help guide your decision. You can also see how each airline stacks up 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

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
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

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Love Field. 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 Chicago Midway Airport to Dallas Love Field Airport?

    For as low as $147, Southwest can have you in Dallas Love Field Airport from Chicago Midway Airport in 4h 55m. There are 793 mi between Chicago Midway Airport and Dallas Love Field Airport.

  • What are the cheapest airlines flying from Chicago Midway Airport to Dallas Love Field Airport round-trip?

    Our cheapest airline available from Chicago Midway Airport to Dallas Love Field Airport is Frontier. Our recent data shows that you can find tickets from as low as $86 on this airline. An additional option worth looking into is Southwest, starting at $157. Frontier is priced at 68% lower than the current average price of a flight leaving 3 months from now.

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

    The cheapest flight price from Chicago Midway Airport to Dallas Love Field Airport is $71. On average you can expect to pay $273. The most popular route, (Chicago Midway - Dallas Love Field), can usually be booked for $141.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Dallas Love Field Airport (average of $287). Flying from Chicago Midway Airport to Dallas Love Field Airport in March is currently the most expensive (average of $382). 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

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Alternative routes for Midway to Love Field

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dallas/Fort Worth flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Love Field flights

Top 2 airlines flying from Midway to Love Field

Discover the top 2 airlines that operate flights from Midway to Love Field. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$86Average$179FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$289FlexibilityNo cancel feeOn-time63%

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