DAL - MDW

$59 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 1/28. 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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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

Fri, Jan 9 - Sun, Jan 11
Southwest Logo
2:35 pm - 4:45 pmDAL-MDW
2h 10mnonstop
Southwest Logo
7:40 am - 10:15 amMDW-DAL
2h 35mnonstop
$117Southwest
Find Deal
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
12:55 pm - 4:25 pmDAL-MDW
3h 30m1 stop
Southwest Logo
8:30 pm - 10:55 pmMDW-DAL
2h 25mnonstop
$142Southwest
Find Deal
Fri, Jan 9 - Mon, Jan 12
Southwest Logo
10:25 am - 12:35 pmDAL-MDW
2h 10mnonstop
Southwest Logo
10:00 am - 2:15 pmMDW-DAL
4h 15m1 stop
$143Southwest
Find Deal
Mon, Feb 2 - Mon, Feb 9
Southwest Logo
9:25 am - 1:25 pmDAL-MDW
4h 00m1 stop
Southwest Logo
7:40 am - 10:15 amMDW-DAL
2h 35mnonstop
$147Southwest
Find Deal
Wed, Jan 21 - Thu, Jan 22
Southwest Logo
12:25 pm - 6:05 pmDAL-MDW
5h 40m2 stops
Southwest Logo
5:55 am - 8:30 amMDW-DAL
2h 35mnonstop
$152Southwest
Find Deal
Wed, Dec 3 - Sat, Dec 6
Southwest Logo
6:45 am - 8:55 amDAL-MDW
2h 10mnonstop
Southwest Logo
6:25 am - 8:50 amMDW-DAL
2h 25mnonstop
$157Southwest
Find Deal
Sat, Jan 10 - Sat, Jan 10
Southwest Logo
12:55 pm - 4:25 pmDAL-MDW
3h 30m1 stop
Southwest Logo
7:40 pm - 10:10 pmMDW-DAL
2h 30mnonstop
$158Southwest
Find Deal
Fri, Jan 9 - Sun, Jan 11
Southwest Logo
10:25 am - 12:35 pmDAL-MDW
2h 10mnonstop
Southwest Logo
7:55 am - 1:15 pmMDW-DAL
5h 20m1 stop
$162Southwest
Find Deal
Wed, Dec 3 - Wed, Dec 10
Southwest Logo
5:05 pm - 7:20 pmDAL-MDW
2h 15mnonstop
Southwest Logo
10:05 am - 2:30 pmMDW-DAL
4h 25m1 stop
$163Southwest
Find Deal
Wed, Dec 24 - Fri, Dec 26
Delta Logo
4:55 pm - 10:22 pmDAL-MDW
5h 27m1 stop
Delta Logo
5:05 pm - 10:33 pmMDW-DAL
5h 28m1 stop
$211Delta
Find Deal

Everything you should know

Top airlines
Southwest
Cheapest • from $117 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
April
Cheapest • 42% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$117
Overall average: $228
Southwest
Fri 1/9Sun 1/11
DAL - MDW • Non-stop
Cheapest one-way
$59
Overall average: $418
Southwest
Wed 1/28
DAL - MDW • Non-stop
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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!
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.

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 Saturdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Sunday 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 April, where tickets cost $174 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $384 and $368 respectively.

Good to know

Low seasonSeptember
Cheapest flight$59
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 13% lower on average.
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 $59 for a one-way ticket and $117 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, Alaska Airlines, and Delta 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 $178 or less one-way and $197 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 4241 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

2.0 MediocreThomas, Oct 2025SAT - STL
Read more Southwest reviews

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

AC sub par. WiFi not working correctly. Ac sucked. Seats very narrow.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

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

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