MDW - DAL

$124 Find Cheap Flights from Chicago Midway Airport to Dallas Love Field - Compare and Save

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Everything you should know

Cheapest round-trip
$204
Typical prices: $268-$433
Southwest
Wed 12/19Fri 12/21
MDW - DAL • 1 stop
Cheapest non-stop
$216
Typical prices: $269-$434
Southwest
Wed 12/12Wed 12/19
MDW - DAL • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 26m
Direct flights
+1
Direct flights
+1
When to book
17 weeks
in advance
Our data shows that travelers who book at least 17 weeks in advance save around 55% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 23% price drop
June
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Dallas Love Field Airport!
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Booking Insights
Flight Deals

Cheap Flights from Midway to Love Field (MDW-DAL)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Love Field

Sat, Feb 20 - Sat, Feb 27
Southwest Logo
10:00 am - 1:55 pmMDW  Chicago Midway-DAL Dallas Love Field
3h 55m1 stop Memphis
Southwest Logo
11:10 am - 4:25 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 15m1 stop Tulsa
$204Southwest
Sat, Dec 19 - Mon, Dec 21
Southwest Logo
4:20 pm - 8:25 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 05m1 stop Omaha Eppley Airfield
Southwest Logo
5:00 pm - 9:05 pmDAL  Dallas Love Field-MDW Chicago Midway
4h 05m1 stop Nashville Intl
$204Southwest
Wed, Jan 6 - Sun, Jan 10
Southwest Logo
8:25 am - 1:20 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 55m1 stop Atlanta Hartsfield-Jackson
Southwest Logo
7:10 am - 9:20 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
$205Southwest
Fri, Jan 8 - Sun, Jan 10
Southwest Logo
10:00 am - 2:00 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 00m1 stop Memphis
Southwest Logo
7:10 am - 9:20 amDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
$205Southwest
Sun, Dec 6 - Thu, Dec 10
Southwest Logo
7:20 am - 9:45 amMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
Southwest Logo
1:20 pm - 5:15 pmDAL  Dallas Love Field-MDW Chicago Midway
3h 55m1 stop Milwaukee-Mitchell
$205Southwest
Thu, Dec 17 - Sun, Dec 20
Southwest Logo
10:15 am - 2:30 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 15m1 stop Birmingham
Southwest Logo
8:10 pm - 10:20 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
$205Southwest
Fri, Dec 18 - Mon, Dec 21
Southwest Logo
5:25 pm - 9:40 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 15m1 stop Birmingham
Southwest Logo
5:30 pm - 11:00 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 30m1 stop Lambert-St Louis
$209Southwest
Fri, Nov 13 - Sun, Nov 15
Southwest Logo
8:20 pm - 10:50 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
Southwest Logo
7:35 pm - 12:10 amDAL  Dallas Love Field-MDW Chicago Midway
4h 35m1 stop Austin Bergstrom
$209Southwest
Sat, Feb 20 - Sat, Feb 27
Delta Logo
1:00 pm - 10:32 pmMDW  Chicago Midway-DAL Dallas Love Field
9h 32m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
2:15 pm - 10:10 pmDAL  Dallas Love Field-MDW Chicago Midway
7h 55m1 stop Atlanta Hartsfield-Jackson
$214Delta
Sat, Dec 5 - Wed, Dec 9
Delta Logo
6:00 am - 2:17 pmMDW  Chicago Midway-DAL Dallas Love Field
8h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:06 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 58m1 stop Atlanta Hartsfield-Jackson
$249Delta
Booking Insights

Price, demand and travel trends for Chicago Midway Airport to Dallas Love Field Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Chicago Midway Airport to Dallas Love Field Airport?

Round-trip flights from Chicago Midway Airport to Dallas Love Field Airport typically range from $268 to $433. The lowest price found in the past 5 days was $204, on Southwest.

What's the cheapest day of the week to fly from Chicago Midway Airport to Dallas Love Field Airport?

Based on deals KAYAK users found in the last 12 months, Thursday is the cheapest day of the week to fly from Chicago Midway Airport to Dallas Love Field Airport. It’s 14% cheaper than the average day, while Monday is the most expensive, with prices 20% higher.

What’s the cheapest month to fly from Chicago Midway Airport to Dallas Love Field Airport?

•January is the cheapest month to fly from Chicago Midway Airport to Dallas Love Field Airport at $269 round-trip.
•July ($411) and August ($378) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 52% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from Chicago Midway Airport to Dallas Love Field Airport are cheapest 17 weeks before departure. Booking in this window typically costs about 55% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Chicago Midway Airport to Dallas Love Field Airport flights

Low season

December

Cheapest flight

$124
Beat the crowds with an average 34% drop in travelers.
The most popular month to fly with an average 48% increase in travelers.
One-way flight from Chicago Midway Airport to Dallas Love Field Airport

When to book flights from Midway to Love Field

Are your dates flexible? Find out the best times to travel from Midway to Love Field based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Chicago Midway Airport to Dallas Love Field Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Chicago Midway Airport to Dallas Love Field Airport?

    These are the earliest and latest flight times available from Chicago Midway Airport to Dallas Love Field Airport:

    • Earliest: departs at 5:00 am and lands at 7:26 am
    • Latest: departs at 9:20 pm and lands at 11:46 pm.

    The flight takes about 2h 26m.

  • What cabin classes can I book on flights from Chicago Midway Airport to Dallas Love Field Airport?

    Only Economy Class is available on flights from Chicago Midway Airport to Dallas Love Field Airport.

  • How long is a flight from Chicago Midway Airport to Dallas Love Field Airport?

    A nonstop flight from Chicago Midway Airport to Dallas Love Field Airport takes 2h 26m, covering 793 miles.

  • Do I need a passport to fly from Chicago Midway Airport to Dallas Love Field Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Chicago Midway Airport to Dallas Love Field Airport flight?

    Round-trip flights from Chicago Midway Airport to Dallas Love Field Airport range from $268 to $433, with an average of $349 over the past 12 months. Anything below $268 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Dallas Love Field Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 29% above the $349 route average. Book 17 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Chicago Midway Airport to Dallas Love Field Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $159 round-trip via Louisville Intl (SDF), compared to $350 for nonstop.

  • What is the standard checked-bag allowance on flights from Chicago Midway Airport to Dallas Love Field Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Chicago Midway Airport to Dallas Love Field Airport?

    The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and American Airlines. Other aircraft seen on the route include Boeing 737-800 Passenger/BBJ2 (winglets) variants.

  • How are flight departures from Chicago Midway Airport to Dallas Love Field Airport spread across the day?

    Morning is the busiest departure period on Chicago Midway Airport to Dallas Love Field Airport flights, with 60% of flights leaving in that window. Afternoon departures account for 20%, evening flights for 20%, and night flights for 0%.

  • Have flight prices from Chicago Midway Airport to Dallas Love Field Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $204 to $1,821. That means the highest observed fare was about 9x higher than the lowest one.

  • Which airlines offer Wi-Fi on Chicago Midway Airport to Dallas Love Field Airport flights?

    JetBlue is the only airline on the Chicago Midway Airport to Dallas Love Field Airport route offering in-flight Wi-Fi. Pricing depends on fare class.

  • How are flight prices from Chicago Midway Airport to Dallas Love Field Airport looking right now?

    One-way fares from Chicago Midway Airport to Dallas Love Field Airport are currently lower than usual. Average one-way flight prices are about $126, which is 45% below the typical average for this route.

  • What car rental options are available at Dallas Love Field Airport (DAL)?

    Dallas Love Field Airport (DAL) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:

    • Easirent
    • Thrifty
    • Dollar
    • Hertz
    • Budget

  • Which airports can I use when flying from Chicago Midway Airport to Dallas Love Field Airport?

    Flights from Chicago Midway Airport to Dallas Love Field Airport usually depart from Chicago Midway (MDW) and arrive at Dallas Love Field (DAL).

  • Which airports do connecting flights from Chicago Midway Airport to Dallas Love Field Airport pass through?

    Most connecting flights from Chicago Midway Airport to Dallas Love Field Airport pass through Louisville Intl (SDF), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Chicago Midway Airport to Dallas Love Field Airport?

    Yes. Flexible dates can save you up to 29% on flights from Chicago Midway Airport to Dallas Love Field Airport. Thursday is the cheapest departure day at $302 round-trip on average, while Monday is the most expensive at $420, a difference of $118.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Chicago Midway Airport to Dallas Love Field Airport?

    Only Southwest operates flights between Chicago Midway Airport and Dallas Love Field Airport.

  • What popular places can I visit in Dallas Love Field Airport?

    Some of the most popular sights in Dallas Love Field Airport are American Airlines Center, Kay Bailey Hutchison Convention Center and Dallas World Aquarium. These are among the most viewed places in Dallas Love Field Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Chicago Midway Airport to Dallas Love Field Airport flights?

    Among airlines operating Chicago Midway Airport to Dallas Love Field Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Chicago Midway Airport to Dallas Love Field Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class
    • JetBlue: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Chicago Midway Airport to Dallas Love Field Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Monday. On this route, Thursday flights average $302, about $118 less than Monday fares (28% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 17 weeks before you fly. On this route, that window historically saves about 55% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Dallas Love Field Airport trip for January. Fares historically average $269 round-trip in that month - typically $142 less than the most expensive month, which is July (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Louisville Intl Airport (SDF) can be cheaper than flying direct. The cheapest layover option averages $159 round-trip on this route - about $191 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Dallas Love Field Airport.

    • Dallas Love Field Inn
    • Wingate by Wyndham Dallas Love Field
    • DoubleTree by Hilton Dallas - Love Field

Prefer to fly direct from Chicago Midway Airport to Dallas Love Field?

 
Find which airlines fly direct from Chicago Midway Airport to Dallas Love Field Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to Dallas Love Field

Monday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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Direct returns

Dallas Love Field to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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More options for your flight from Midway to Love Field

Complete your trip to Love Field with a hotel stay or car rental

Car rentals in Dallas
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