MDW - DAL

$59 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 1/15. 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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Everything you should know

Cheapest round-trip
$117
Overall average: $240
Southwest
Fri 1/9Sun 1/11
MDW - DAL • Non-stop
Cheapest one-way
$59
Typical prices: $177-$335
Southwest
Thu 1/15
MDW - DAL • Non-stop
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 • 36% price drop
October
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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 Love Field!
Flight Deals
Booking Insights
Flight 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

Fri, Jan 9 - Sun, Jan 11
Southwest Logo
5:55 am - 8:30 amMDW-DAL
2h 35mnonstop
Southwest Logo
6:35 am - 8:45 amDAL-MDW
2h 10mnonstop
$117Southwest
Find Deal
Thu, Dec 25 - Tue, Jan 20
Southwest Logo
8:30 pm - 10:55 pmMDW-DAL
2h 25mnonstop
Southwest Logo
7:00 am - 9:10 amDAL-MDW
2h 10mnonstop
$131Southwest
Find Deal
Thu, Dec 25 - Tue, Jan 20
Southwest Logo
4:40 pm - 8:55 pmMDW-DAL
4h 15m1 stop
Southwest Logo
2:35 pm - 4:45 pmDAL-MDW
2h 10mnonstop
$141Southwest
Find Deal
Thu, Jan 8 - Thu, Jan 15
Southwest Logo
10:00 am - 2:15 pmMDW-DAL
4h 15m1 stop
Southwest Logo
10:40 am - 12:50 pmDAL-MDW
2h 10mnonstop
$143Southwest
Find Deal
Wed, Dec 3 - Sat, Dec 6
Southwest Logo
5:00 am - 7:30 amMDW-DAL
2h 30mnonstop
Southwest Logo
4:50 pm - 7:05 pmDAL-MDW
2h 15mnonstop
$147Southwest
Find Deal
Mon, Dec 22 - Wed, Dec 31
Southwest Logo
5:25 am - 7:50 amMDW-DAL
2h 25mnonstop
Southwest Logo
6:45 am - 8:55 amDAL-MDW
2h 10mnonstop
$151Southwest
Find Deal
Thu, Jan 8 - Thu, Jan 15
Southwest Logo
5:55 am - 8:30 amMDW-DAL
2h 35mnonstop
Southwest Logo
2:50 pm - 7:55 pmDAL-MDW
5h 05m2 stops
$152Southwest
Find Deal
Wed, Dec 3 - Sat, Dec 6
Southwest Logo
10:05 am - 2:30 pmMDW-DAL
4h 25m1 stop
Southwest Logo
4:50 pm - 7:05 pmDAL-MDW
2h 15mnonstop
$153Southwest
Find Deal
Wed, Dec 17 - Tue, Jan 6
Delta Logo
12:50 pm - 5:53 pmMDW-DAL
5h 03m1 stop
Delta Logo
10:20 am - 4:25 pmDAL-MDW
6h 05m1 stop
$177Delta
Find Deal
Wed, Nov 19 - Thu, Nov 20
Delta Logo
10:47 am - 5:50 pmMDW-DAL
7h 03m1 stop
Delta Logo
6:00 am - 11:52 amDAL-MDW
5h 52m1 stop
$211Delta
Find Deal
Booking Insights

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, Wednesday 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 October, where the average cost of round-trip tickets is $389 and $350 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Dallas Love Field Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $237 on average.

Good to know

Low seasonJune
Cheapest flight$59
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 23% increase in price.
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 $59 for a one-way ticket and $117 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.

  • Which is the best airline for flights from Chicago to Dallas, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Dallas are Southwest and Frontier. With an average price for the route of $293 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $262 and an overall rating of 5.8.

  • 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 $152 or less one-way and $244 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 4244 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

2.0 MediocrePrincess, Oct 2025MSY - DAL
Read more Southwest reviews

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

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.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

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

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