DAL - MDW

$138 Find Cheap Flights from Dallas Love Field to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Love Field to Midway departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$276
Typical prices: $464-$342
Southwest
Sat 5/30Sat 6/6
DAL - MDW • Non-stop
Cheapest one-way
$138
Typical prices: $180-$281
Southwest
Sat 5/30
DAL - MDW • Non-stop
Top airlines
Cheapest • from $276 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 2h 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 46% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Love Field to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Love Field to Midway

Sat, May 30 - Sat, Jun 6
Southwest Logo
7:35 pm - 9:45 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
7:00 pm - 9:15 pm
MDW
-
DAL
2h 15mnonstop
$276Southwest
Wed, Jun 17 - Wed, Jun 24
Southwest Logo
3:00 pm - 5:15 pm
DAL
-
MDW
2h 15mnonstop
Southwest Logo
1:55 pm - 4:15 pm
MDW
-
DAL
2h 20mnonstop
$281Southwest
Sat, Jun 6 - Sat, Jun 6
Southwest Logo
1:30 pm - 4:55 pm
DAL
-
MDW
3h 25m
1 stop
Southwest Logo
7:00 pm - 9:15 pm
MDW
-
DAL
2h 15mnonstop
$284Southwest
Wed, Jun 17 - Wed, Jun 24
Southwest Logo
8:00 am - 12:10 pm
DAL
-
MDW
4h 10m
1 stop
Southwest Logo
6:30 am - 8:50 am
MDW
-
DAL
2h 20mnonstop
$287Southwest
Tue, Jun 9 - Thu, Jun 11
Southwest Logo
9:55 pm - 12:05 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
6:40 am - 9:00 am
MDW
-
DAL
2h 20mnonstop
$289Southwest
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
9:55 pm - 12:05 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
DAL
2h 15mnonstop
$291Southwest
Wed, Jun 17 - Sat, Jun 20
Southwest Logo
12:00 pm - 5:00 pm
DAL
-
MDW
5h 00m
2 stops
Southwest Logo
6:30 am - 8:50 am
MDW
-
DAL
2h 20mnonstop
$292Southwest
Tue, Jun 9 - Thu, Jun 11
Southwest Logo
4:30 pm - 8:45 pm
DAL
-
MDW
4h 15m
1 stop
Southwest Logo
12:20 pm - 2:35 pm
MDW
-
DAL
2h 15mnonstop
$295Southwest
Wed, Jun 10 - Wed, Jun 17
Southwest Logo
4:30 pm - 8:45 pm
DAL
-
MDW
4h 15m
1 stop
Southwest Logo
10:00 am - 2:20 pm
MDW
-
DAL
4h 20m
1 stop
$296Southwest
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
8:00 am - 12:10 pm
DAL
-
MDW
4h 10m
1 stop
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
DAL
2h 15mnonstop
$297Southwest
Booking Insights

KAYAK's insights & trends for Love Field to Midway flights

Get data-powered insights and trends into flights from Love Field to Midway to help you find the cheapest flights, the best time to fly and much more.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Dallas Love Field Airport to Chicago Midway Airport departing in May.

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

The average price of all round-trip flights from Dallas Love Field Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Dallas Love Field to Chicago Midway Airport, look for departures on Wednesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Thursday is the cheapest day to fly and Monday is the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Dallas Love Field Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Dallas Love Field Airport to Chicago Midway Airport is December, where tickets cost $186 (return) on average. On the other hand, the most expensive months are October and May, where the average cost of round-trip tickets is $464 and $421 respectively.

Good to know

Low seasonJanuary
Cheapest flight$138
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 3% increase in price.
Flight from Dallas Love Field 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Dallas Love Field to Chicago Midway Airport flights

  • What is the cheapest flight from Dallas Love Field Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Dallas Love Field Airport to Chicago Midway Airport was $138 for a one-way ticket and $276 for a round-trip.

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

    No, a passport isn't needed to fly from Dallas Love Field to Chicago Midway Airport. However, local authorities might ask for an official ID.

  • Which airlines offer Wi-Fi service onboard planes from Dallas Love Field to Chicago Midway Airport?

    American Airlines, JetBlue, Delta, and Alaska Airlines offer inflight Wi-Fi service on the Dallas Love Field to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Dallas Love Field to Chicago Midway Airport?

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the Dallas Love Field to Chicago Midway Airport flight route.

  • On which days can I fly direct from Dallas Love Field to Chicago Midway Airport?

    There are nonstop flights from Dallas Love Field to Chicago Midway Airport on a daily basis.

  • How does KAYAK find such low prices on flights from Dallas Love Field to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Dallas Love Field to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Dallas Love Field to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Dallas Love Field is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Dallas Love Field to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Dallas Love Field with another airline. Booking your flights between Dallas Love Field and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Dallas Love Field to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Dallas Love Field up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Dallas Love Field Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $168 or less one-way and $335 or less round-trip.

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

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Dallas Love Field to Chicago Midway.
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

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Dallas Love Field

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Love Field to Midway

 
See real verified KAYAK customer reviews for airlines flying from Dallas to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Love Field to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4295 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Everything you need to know for your flight from Love Field to Midway

Information on your arrival and departure airports