HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$74+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Love Field to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 agosto 14, 2025.

Round-trip from

$129
(Southwest)

One-way from

$74
(Southwest)

Popular in

November

Cheapest in

April

Average price

$304

Good round-trip deal

$177 or less

Good one-way deal

$152 or less
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. 7% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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.
Search Deals

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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/14. 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.
mié. 9/1012:15 pmDAL - MDW
Nonstop2h 15mSouthwest
mié. 9/105:30 pmMDW - DAL
Nonstop2h 15mSouthwest
Deal found 8/14$129
This Southwest deal was found by Cheapflights users on 8/14. 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.
mié. 9/2410:20 amDAL - MDW
Nonstop2h 15mSouthwest
sáb. 9/273:15 pmMDW - DAL
Nonstop2h 15mSouthwest
Deal found 8/14$138
This Southwest deal was found by Cheapflights users on 8/14. 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.
jue. 9/46:00 amDAL - MDW
Nonstop2h 15mSouthwest
sáb. 9/63:15 pmMDW - DAL
Nonstop2h 15mSouthwest
Deal found 8/14$147
This Southwest deal was found by Cheapflights users on 8/14. 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.
lun. 9/83:20 pmDAL - MDW
2 stops5h 05mSouthwest
mar. 9/93:35 pmMDW - DAL
Nonstop2h 15mSouthwest
Deal found 8/14$153
This Southwest deal was found by Cheapflights users on 8/14. 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.
dom. 11/27:20 amDAL - MDW
Nonstop2h 15mSouthwest
mar. 11/118:25 amMDW - DAL
Nonstop2h 25mSouthwest
Deal found 8/14$155
This Southwest deal was found by Cheapflights users on 8/14. 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.
mié. 9/247:35 amDAL - MDW
1 stop4h 35mSouthwest
jue. 9/2511:45 amMDW - DAL
1 stop4h 25mSouthwest
Deal found 8/14$158
This Southwest deal was found by Cheapflights users on 8/14. 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.
vie. 10/316:00 pmDAL - MDW
Nonstop2h 15mSouthwest
lun. 11/35:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 8/14$163
This Southwest deal was found by Cheapflights users on 8/14. 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.
vie. 10/179:55 pmDAL - MDW
Nonstop2h 10mSouthwest
lun. 10/205:25 amMDW - DAL
Nonstop2h 15mSouthwest
Deal found 8/14$164

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 agosto 14, 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

mar. 9/23

8:10 am-10:25 am

Nonstop2h 15m

Chicago Midway

mié. 9/24

12:50 pm-3:05 pm

Nonstop2h 15m

$129

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mié. 9/10

8:10 am-10:25 am

Nonstop2h 15m

Chicago Midway

mié. 9/17

5:30 pm-7:45 pm

Nonstop2h 15m

$129

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mar. 9/16

2:50 pm-5:10 pm

Nonstop2h 20m

Chicago Midway

mié. 9/17

12:50 pm-3:05 pm

Nonstop2h 15m

$129

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mié. 9/17

12:15 pm-2:30 pm

Nonstop2h 15m

Chicago Midway

mié. 9/17

8:05 pm-10:20 pm

Nonstop2h 15m

$129

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mar. 9/9

5:00 pm-7:15 pm

Nonstop2h 15m

Chicago Midway

mar. 9/16

8:05 pm-10:20 pm

Nonstop2h 15m

$129

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

lun. 10/20

9:55 pm-12:05 am

Nonstop2h 10m

Chicago Midway

mié. 10/22

6:55 pm-9:15 pm

Nonstop2h 20m

$138

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mié. 9/24

10:20 am-12:35 pm

Nonstop2h 15m

Chicago Midway

sáb. 9/27

7:25 pm-9:40 pm

Nonstop2h 15m

$138

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

lun. 9/8

2:20 pm-4:35 pm

Nonstop2h 15m

Chicago Midway

mié. 9/10

3:35 pm-5:50 pm

Nonstop2h 15m

$138

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

sáb. 9/27

4:45 pm-7:00 pm

Nonstop2h 15m

Chicago Midway

mar. 9/30

5:30 pm-7:45 pm

Nonstop2h 15m

$138

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

mié. 9/17

10:20 am-12:35 pm

Nonstop2h 15m

Chicago Midway

jue. 9/18

8:55 pm-11:10 pm

Nonstop2h 15m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 17 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 agosto 14, 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 29% 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 August 10, 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 agosto 14, 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
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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.

  • 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 $254, our data shows the cheapest flight currently is $46. When looking at the most popular route, (Dallas Love Field - Chicago Midway), you can expect to pay $129 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$298FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.