MDW - DAL

$79 Find Cheap Flights from Chicago Midway Airport to Dallas Love Field

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Love Field departing on 9/11. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Dallas Love Field Airport

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

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Love Field 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 Midway to Love Field

Thu, Aug 21 - Mon, Aug 25
Southwest Logo
8:55 pm - 11:10 pmMDW-DAL
2h 15mnonstop
Southwest Logo
6:00 am - 8:15 amDAL-MDW
2h 15mnonstop
$157Southwest
Find Deal
Thu, Aug 21 - Sat, Aug 23
Southwest Logo
9:35 am - 3:00 pmMDW-DAL
5h 25m1 stop
Southwest Logo
6:45 am - 9:00 amDAL-MDW
2h 15mnonstop
$163Southwest
Find Deal
Thu, Sep 4 - Thu, Sep 11
Southwest Logo
7:10 am - 12:25 pmMDW-DAL
5h 15m1 stop
Southwest Logo
8:20 pm - 10:30 pmDAL-MDW
2h 10mnonstop
$167Southwest
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
4:00 pm - 8:10 pmMDW-DAL
4h 10m1 stop
Southwest Logo
1:40 pm - 5:45 pmDAL-MDW
4h 05m1 stop
$168Southwest
Find Deal
Wed, Aug 6 - Thu, Aug 14
Southwest Logo
9:00 am - 1:10 pmMDW-DAL
4h 10m1 stop
Southwest Logo
1:40 pm - 5:45 pmDAL-MDW
4h 05m1 stop
$172Southwest
Find Deal
Fri, Aug 29 - Mon, Sep 1
Southwest Logo
5:00 pm - 7:15 pmMDW-DAL
2h 15mnonstop
Southwest Logo
6:00 am - 8:15 amDAL-MDW
2h 15mnonstop
$177Southwest
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
4:00 pm - 8:10 pmMDW-DAL
4h 10m1 stop
Southwest Logo
3:20 pm - 8:25 pmDAL-MDW
5h 05m2 stops
$178Southwest
Find Deal
Thu, Aug 7 - Mon, Aug 11
Southwest Logo
11:45 am - 4:10 pmMDW-DAL
4h 25m1 stop
Southwest Logo
3:20 pm - 8:25 pmDAL-MDW
5h 05m2 stops
$182Southwest
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Tue, Jul 29 - Tue, Aug 12
Delta Logo
5:05 pm - 11:44 pmMDW-DAL
6h 39m1 stop
Delta Logo
3:52 pm - 9:49 pmDAL-MDW
5h 57m1 stop
$197Delta
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Fri, Jul 25 - Mon, Aug 11
Delta Logo
6:47 pm - 11:44 pmMDW-DAL
4h 57m1 stop
Delta Logo
3:52 pm - 9:49 pmDAL-MDW
5h 57m1 stop
$208Delta
Find Deal
Useful Info

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

Get data-powered insights and trends into flights from Midway to Love Field 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 Chicago Midway Airport to Dallas Love Field?

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Dallas Love Field 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 Chicago Midway Airport to Dallas Love Field Airport is April, where tickets cost $182 (return) on average. On the other hand, the most expensive months are November and February, where the average cost of round-trip tickets is $383 and $349 respectively.

Good to know

Low seasonJune
High seasonSeptember
Cheapest flight$79
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago Midway Airport to Dallas Love Field

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
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 Chicago Midway Airport to Dallas Love Field flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Dallas Love Field Airport was $79 for a one-way ticket and $157 for a round-trip.

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

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

  • Which airports will I be using when flying from Chicago Midway Airport to Dallas Love Field?

    On your way to Dallas Love Field, you’ll fly out from Chicago Midway. You’ll be landing at Dallas Love Field.

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

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

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

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

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

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

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

    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 Chicago Midway Airport to Dallas Love Field.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Dallas Love Field from Chicago Midway Airport 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 Chicago Midway Airport to Dallas Love Field?

    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 Dallas Love Field with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and DAL 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 Chicago Midway Airport to Dallas Love Field?

    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 Dallas Love Field from Chicago Midway Airport 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 Chicago Midway Airport to Dallas Love Field Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $119 or less one-way and $188 or less round-trip.

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

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

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

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

Reviews of the top airlines flying from Midway to Love Field

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Dallas. 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 Midway to Love Field? 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 4278 reviews
7.6Entertainment
8.6Crew
8.2Boarding
8.0Comfort
7.0Food
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

First, my flight was a usual flight nothing exceptional or unexpected. Over all it was a normal, good flight! Second, your questionaire is wholly lacking in the proper options to which one can answer a question. Often on short flights, there is no food let alone entertainment so why isn't that reflected in your questionaire? A simple "not applicable" would cover that issue appropriately but no, your form arbitrarily enters an answer based on the initial assessment which normally isn't factual. Until you provide an accurate means of assessing flights, I'll no longer be completing of these unimpressive and misleading assessements. Thank you!

Easy to book and to get check in and get on and off.

Excellent experience. WiFi worked on this leg of My trip

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Very bad! No good service delayed my second connection flight

The confirmation # CK8GNW and my name was not recognized/in Frontier system. I was able to check in on Frintier app so i went to the Frontier ticket agent, at time they told me that my name/ confirmation did not show up as a purchased ticket. I had to purchase a new ticket that cost $289.00 one way.

Flight was late. Missed connecting in Denver. My new flight is more than 24 hours later and I have no room, vouchers, or compensation, and might also be bumped from the one tomorrow.

Frontier is terrible. Paid for exit row, not given exit row, refused to refund fee.

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

We had to wait in line over an hour just to check our bags. It's a good thing we were so early to the airport. Only one clerk was working and the line was around the corner and down the hall. No good. I felt bad for her. Not sure how she kept her sanity with all the upset people. Then we get to our gate and there is no seating. Everyone was standing. Then I realize it is not a gate at all, we still have to be shuttled to our airplane. Ugh. Then we were late taking off and missed a window of opportunity before the airport runways were shut down for some reason. (not frontier's fault the runway shut down.) The seats on the airline are crammed and there is no cushion. Never had a tighter seating arrangement while flying. My 6' 4" husband was absolutely miserable the whole time with knees digging in to the seat in front of him. You think you are getting a good deal on a ticket, and then wham! I had to pay 75 dollars for our checked bags and 75 dollars for a carry on. No other airline does that!!! And also, there is a 40 pound weight limit on checked bags... Would have been cheaper flying with another airline, and I would have at least gotten a snack and drink. Was thankful for the tiny cup of water at least.

This was one of the first frontier airline flights this spring that wasn't delayed. It actually left on time. Some of the flight crew did not look happy, they didn't smile when the passengers were boarding or getting off the plane, and the passengers initiated greetings, not the staff. To me this was an odd experience to have with any flight/airline. I had a bad experience booking this flight. The price didn't solidify until late hours into the night. Ever time I purchased the ticket, I either received a denial email or an error because the price has changed, but it was never reflected on the flyfrontier or kayak websites until way after midnight on the date of travel. This caused me anxiety and irritation with the websites. Then I noticed a mishap with my name on my voucher as I went to check in, it was incorrect. When I proceeded to correct it, Frontier had no easy, let alone free, way to remedy it. I couldn't correct my name without a $75 charge, I couldn't cancel my voucher to repurchase it with the correct name without a $100 charge, because it was too close to departure. Then calling frontier was nearly impossible to remedy the situation with a human. It's already difficult to want to choose frontier because of all the upcharges, but you feel kinda trapped into doing so because it's the more affordable airline.

They canceled flight. Hard to believe there was even a plane incoming for us to get on

The worst. We never made our connection and they did absolutely nothing to help us at the airport.

Our flight was cancelled. They could do nothing to help us get another flight that was timely. Because the first leg was cancelled we were unable to get to our connection. We had to book on an entirely different airline for today. So we spent more money, lost a day of vacation and will never fly Frontier again, so the 'we are sorry, here is $100 credit' is a joke since we won't be flying on Frontier.

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

Information on your arrival and departure airports

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