MDW - DAL

$56 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 4/4. 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 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
$129
Overall average: $382
Southwest
Sat 3/14Sat 3/21
MDW - DAL • Non-stop
Cheapest one-way
$56
Typical prices: $73-$201
Southwest
Sat 4/4
MDW - DAL • Non-stop
Top airlines
Southwest
Cheapest • from $129 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
April
Cheapest • 35% price drop
February
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

Sat, Mar 14 - Sat, Mar 21
Southwest Logo
7:00 pm - 9:30 pm
MDW
-
DAL
2h 30mnonstop
Southwest Logo
9:50 am - 12:00 pm
DAL
-
MDW
2h 10mnonstop
$129Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
4:20 pm - 6:45 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
6:55 pm - 9:05 pm
DAL
-
MDW
2h 10mnonstop
$152Southwest
Wed, Mar 11 - Wed, Mar 18
Southwest Logo
6:00 am - 8:35 am
MDW
-
DAL
2h 35mnonstop
Southwest Logo
6:00 am - 8:10 am
DAL
-
MDW
2h 10mnonstop
$157Southwest
Sat, Feb 28 - Wed, Mar 4
Southwest Logo
6:50 am - 9:25 am
MDW
-
DAL
2h 35mnonstop
Southwest Logo
7:00 am - 9:10 am
DAL
-
MDW
2h 10mnonstop
$159Southwest
Wed, Mar 11 - Tue, Mar 17
Southwest Logo
6:00 am - 8:35 am
MDW
-
DAL
2h 35mnonstop
Southwest Logo
12:55 pm - 5:05 pm
DAL
-
MDW
4h 10m
1 stop
$167Southwest
Sat, Feb 28 - Wed, Mar 4
Southwest Logo
4:20 pm - 6:45 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
1:50 pm - 7:05 pm
DAL
-
MDW
5h 15m
1 stop
$169Southwest
Sat, Feb 28 - Sat, Mar 7
Southwest Logo
5:40 am - 10:45 am
MDW
-
DAL
5h 05m
1 stop
Southwest Logo
6:55 pm - 9:05 pm
DAL
-
MDW
2h 10mnonstop
$172Southwest
Mon, Mar 9 - Tue, Mar 10
Southwest Logo
7:00 pm - 9:30 pm
MDW
-
DAL
2h 30mnonstop
Southwest Logo
6:00 am - 8:10 am
DAL
-
MDW
2h 10mnonstop
$175Southwest
Wed, Mar 11 - Tue, Mar 17
Southwest Logo
5:35 pm - 11:05 pm
MDW
-
DAL
5h 30m
1 stop
Southwest Logo
3:55 pm - 9:15 pm
DAL
-
MDW
5h 20m
1 stop
$177Southwest
Tue, May 12 - Sat, May 16
Southwest Logo
4:00 pm - 6:25 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
12:40 pm - 4:50 pm
DAL
-
MDW
4h 10m
1 stop
$181Southwest
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 Saturdays 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 March and November, where the average cost of round-trip tickets is $382 and $347 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 $294 on average.

Good to know

Low seasonJune
Cheapest flight$56
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 19% 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 $56 for a one-way ticket and $129 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, JetBlue, 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 $286 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 5.7.

  • 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 $163 or less one-way and $246 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 4280 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

10.0 ExcellentAnonymous, Feb 2026
STL - DAL
Read more Southwest reviews

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

No delays and arrived to destination 30 min early. Staff was super friendly.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

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

Information on your arrival and departure airports