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DAL - MDW

$139 Find Cheap Flights from Dallas Love Field to Chicago Midway Airport - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$277
Typical prices: $245-$416
Southwest
Mon 10/29Fri 11/2
DAL - MDW • Non-stop
Cheapest one-way
$139
Typical prices: $171-$286
Southwest
Wed 10/24
DAL - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 2h 14m
Direct flights
+1
Direct flights
+1
When to book
15 weeks
in advance
Our data shows that travelers who book at least 15 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
When to travel
January
Cheapest • 37% price drop
June
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Chicago Midway Airport!
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Booking Insights
Flight Deals

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

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

Recent round-trip flight deals from Love Field to Midway

Thu, Oct 29 - Mon, Nov 2
Southwest Logo
10:55 pm - 1:10 amDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:20 am - 7:45 amMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$277Southwest
Tue, Oct 27 - Tue, Nov 3
Southwest Logo
8:05 pm - 10:20 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
10:55 am - 1:25 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Wed, Nov 4 - Sat, Nov 7
Southwest Logo
8:25 pm - 10:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
6:20 pm - 8:55 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 35mnonstop
$277Southwest
Wed, Oct 28 - Wed, Nov 4
Southwest Logo
8:05 pm - 10:20 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Wed, Nov 18 - Sat, Nov 21
Southwest Logo
5:40 pm - 7:55 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:20 am - 7:45 amMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$277Southwest
Thu, Oct 29 - Tue, Nov 3
Southwest Logo
11:55 am - 2:10 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
7:05 am - 9:35 amMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Wed, Nov 18 - Sat, Nov 21
Southwest Logo
5:40 pm - 7:55 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
5:20 am - 7:45 amMDW  Chicago Midway-DAL Dallas Love Field
2h 25mnonstop
$277Southwest
Sat, Nov 14 - Mon, Nov 16
Southwest Logo
12:30 pm - 2:45 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
$277Southwest
Sat, Oct 24 - Tue, Oct 27
Delta Logo
3:59 pm - 10:33 pmDAL  Dallas Love Field-MDW Chicago Midway
6h 34m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:49 pm - 6:05 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 16m1 stop Atlanta Hartsfield-Jackson
$297Delta
Wed, Dec 9 - Tue, Dec 15
Delta Logo
6:06 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 58m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:02 pm - 6:06 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 04m1 stop Atlanta Hartsfield-Jackson
$297Delta
Booking Insights

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

Round-trip flights from Dallas Love Field Airport to Chicago Midway Airport typically range from $245 to $416. The lowest price found in the past 5 days was $277, on Southwest.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Dallas Love Field Airport to Chicago Midway Airport. It’s 17% cheaper than the average day, while Sunday is the most expensive, with prices 16% higher.

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

•January is the cheapest month to fly from Dallas Love Field Airport to Chicago Midway Airport at $208 round-trip.
•July ($396) and June ($375) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 90% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

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

Flights from Dallas Love Field Airport to Chicago Midway Airport are cheapest 15 weeks before departure. Booking in this window typically costs about 45% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

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

Low season

December

Cheapest flight

$139
Beat the crowds with an average 26% drop in travelers.
The most popular month to fly with an average 74% increase in travelers.
One-way flight from Dallas Love Field Airport to Chicago Midway Airport

When to book flights from Love Field to Midway

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

Your Dallas Love Field Airport to Chicago Midway 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 Dallas Love Field Airport to Chicago Midway Airport?

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

    • Earliest: departs at 6:00 am and lands at 8:14 am
    • Latest: departs at 10:55 pm and lands at 1:09 am.

    The flight takes about 2h 14m.

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

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

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

    A nonstop flight from Dallas Love Field Airport to Chicago Midway Airport takes 2h 14m, covering 793 miles.

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

    Round-trip flights from Dallas Love Field Airport to Chicago Midway Airport range from $245 to $416, with an average of $332 over the past 12 months. Anything below $245 counts as a good deal.

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

    Last-minute fares on this route (booked within two weeks of departure) run 31% above the $332 route average. Book 15 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $176 round-trip via Lambert-St Louis (STL), compared to $332 for nonstop.

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

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

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

    Morning is the busiest departure period on Dallas Love Field Airport to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 34%, evening flights for 16%, and night flights for 16%.

  • Have flight prices from Dallas Love Field Airport to Chicago Midway 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 $277 to $1,347. That means the highest observed fare was about 5x higher than the lowest one.

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

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

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

    One-way fares from Dallas Love Field Airport to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $141, which is 34% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

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

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

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

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

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

    Yes. Flexible dates can save you up to 29% on flights from Dallas Love Field Airport to Chicago Midway Airport. Wednesday is the cheapest departure day at $277 round-trip on average, while Sunday is the most expensive at $387, a difference of $110.

    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 Dallas Love Field Airport to Chicago Midway Airport?

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

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

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

    Among airlines operating Dallas Love Field Airport to Chicago Midway 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 Dallas Love Field Airport to Chicago Midway 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 Dallas Love Field Airport to Chicago Midway 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 Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $277, about $110 less than Sunday fares (28% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 15 weeks before you fly. On this route, that window historically saves about 45% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Dallas Love Field Airport to Chicago Midway Airport trip for January. Fares historically average $208 round-trip in that month - typically $188 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 Lambert-St Louis Airport (STL) can be cheaper than flying direct. The cheapest layover option averages $176 round-trip on this route - about $156 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 Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

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

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

Direct departures

Dallas Love Field to Chicago Midway

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Saturday

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Sunday

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Direct returns

Chicago Midway to Dallas Love Field

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Sunday

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More options for your flight from Love Field to Midway

Complete your trip to Midway with a hotel stay or car rental

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