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$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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — MDW
Mar 23 — Mar 301
Sun 3/23
Sun 3/30
1 adult, Economy
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1. Tell us where you want to go
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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 March 18, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$147
(Southwest)

One-way from

$74
(Southwest)

Popular in

July

Cheapest in

April

Average price

$296

Good round-trip deal

$206 or less

Good one-way deal

$134 or less
Provider with most accurate pricing for Dallas Love Field-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Dallas Love Field-Chicago Midway flights.
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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. 23% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 18, 2025.

This Southwest deal was found by Cheapflights users on 3/17. 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 4/108:15 pmDAL - MDW
Nonstop2h 10mSouthwest
Mon 4/1412:10 pmMDW - DAL
Nonstop2h 20mSouthwest
Deal found 3/17$147
This Delta deal was found by Cheapflights users on 3/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/311:56 amDAL - MDW
1 stop6h 03mDelta
Tue 5/1312:48 pmMDW - DAL
1 stop4h 56mDelta
Deal found 3/16$197

Find flights from Love Field to Midway within your budget

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 March 18, 2025.

Fly from

Love Field

Fly to

Midway

Route

Depart

Return

Price

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 4/10

8:15 pm-10:25 pm

Nonstop2h 10m

Chicago Midway

Sun 4/13

7:00 am-9:20 am

Nonstop2h 20m

$147

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 4/12

3:02 pm-10:21 pm

1 stop7h 19m

Chicago Midway

Mon 4/14

4:59 pm-10:12 pm

1 stop5h 13m

$278

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 4/8

11:45 am-2:00 pm

Nonstop2h 15m

$74

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sun 4/20

5:55 am-12:03 pm

1 stop6h 08m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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 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.

Travel insights for flights from Love Field to Midway

Get recent, data-driven insights about flights from Love Field to Midway including ideal travel times, pricing trends, and more.

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 March 18, 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 33% 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 March 16, 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 March 18, 2025.
Get a feel of what it's like to fly with Southwest and Delta from Dallas to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,280 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

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
8.1
Very good
4,280 reviews
Southwest
8.1
Very good
4,280 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

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.
Delta
8.0
Very good
7,908 reviews
Southwest
8.1
Very good
4,280 reviews

Crew

8.7

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Food

7.1

Overall

8.1

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 are the cheapest airlines flying 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 $147. Another airline that can offer you cheap pricing is Delta. Southwest is 52% 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 $280, our data shows the cheapest flight currently is $73. When looking at the most popular route, (Dallas Love Field - Chicago Midway), you can expect to pay $147 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 Dallas Love Field Airport?

Book flights to Dallas Love Field Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 2 airlines flying from Love Field to Midway

Discover the top 2 airlines 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 March 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$161Average$302FlexibilityNo cancel feeOn-time63%
DeltaCheapest$246Average$723FlexibilityNo cancel feeOn-timeN/A
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