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DAL - MDW

Find cheap flights from Dallas Love Field to Chicago Midway Airport from $151

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 4/11. 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
0 bags
Sat 4/27
Sat 5/4

Search 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
In the last 7 days travelers have searched 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Love Field to Midway

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 and deals for you by selecting your travel dates.
Choose your dates
11:20 am - 4:10 pmDAL-MDW
4h 50m1 stop
12:45 pm - 5:44 pmMDW-DAL
4h 59m1 stop
$193Delta
Find Deal
Tue, Apr 30 - Wed, May 1
11:20 am - 4:10 pmDAL-MDW
4h 50m1 stop
12:45 pm - 5:44 pmMDW-DAL
4h 59m1 stop
$218Delta
Find Deal
Tue, Apr 30 - Wed, May 1
3:00 pm - 10:14 pmDAL-MDW
7h 14m1 stop
6:47 pm - 11:50 pmMDW-DAL
5h 03m1 stop
$248Delta
Find Deal
Sat, Apr 27 - Mon, Apr 29
6:00 am - 11:55 amDAL-MDW
5h 55m1 stop
12:45 pm - 5:44 pmMDW-DAL
4h 59m1 stop
$318Delta
Find Deal
Tue, Apr 16 - Tue, Apr 23
7:30 am - 2:54 pmDAL-MDW
7h 24m1 stop
6:00 am - 10:59 amMDW-DAL
4h 59m1 stop
$328Delta
Find Deal
Sat, Jun 22 - Mon, Jul 1
2:35 pm - 7:20 pmDAL-MDW
4h 45m1 stop
11:55 am - 2:15 pmMDW-DAL
2h 20mnonstop
$331Southwest
Find Deal
Mon, Apr 8 - Thu, Apr 11
3:10 pm - 12:50 amDAL-MDW
9h 40m1 stop
9:45 am - 1:55 pmMDW-DAL
4h 10m1 stop
$336Southwest
Find Deal
Mon, Apr 8 - Thu, Apr 11
7:30 am - 2:54 pmDAL-MDW
7h 24m1 stop
6:00 am - 2:00 pmMDW-DAL
8h 00m1 stop
$342Delta
Find Deal
Sat, Jun 22 - Sun, Jun 30
3:10 pm - 12:50 amDAL-MDW
9h 40m1 stop
8:25 am - 4:25 pmMDW-DAL
8h 00m2 stops
$345Southwest
Find Deal
Mon, Apr 8 - Thu, Apr 11
6:20 am - 8:30 amDAL-MDW
2h 10mnonstop
8:25 pm - 10:40 pmMDW-DAL
2h 15mnonstop
$352Southwest
Find Deal
Mon, Apr 8 - Thu, Apr 11

Flights from Love Field to Midway - Travel Insights & Trends

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 flights from Dallas Love Field Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago Midway Airport on a Wednesday and more expensive on a Friday. On your return trip to Dallas Love Field, you should consider flying back on a Sunday, and avoid Mondays for better deals.

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 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 January, where tickets cost $101 on average. On the other hand, the most expensive months are July and June, where the average cost of tickets is $227 and $190 respectively.

How far in advance should I book a flight from Dallas Love Field Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Dallas Love Field Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Dallas Love Field Airport to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 63 days before departure.

Which airlines provide the cheapest flights from Dallas Love Field to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Southwest ($151) and Delta ($213). The cheapest round-trip tickets were found on Delta ($193) and Southwest ($331).

How many flights are there between Dallas Love Field Airport and Chicago Midway Airport per day?

Each day, there are between 7 and 13 nonstop flights that take off from Dallas Love Field Airport and land in Chicago Midway Airport, with an average flight time of 2h 10m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 76 flights. The most frequent day of departure is Friday, when 17% of all weekly flights depart. The fewest flights depart on a Wednesday.

Which cabin class options are there for flights between Dallas Love Field Airport and Chicago Midway Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Dallas Love Field to Chicago Midway Airport take?

The average nonstop flight takes 2h 10m, covering a distance of 793 miles.

What’s the earliest departure time from Dallas Love Field to Chicago Midway Airport?

Early birds can take the earliest flight from Dallas Love Field Airport at 6:00 am and will be landing in Chicago Midway Airport at 8:05 am.

What’s the latest departure time from Dallas Love Field to Chicago Midway Airport?

If you prefer to fly at night, the latest flight from Dallas Love Field Airport to Chicago Midway Airport jets off at 10:10 pm and lands at 12:15 am.

Good to know

Low season

September

High season

December

Cheapest flight

$151
Best time to beat the crowds with an average 53% drop in price.
Most popular time to fly with an average 34% 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 $151 for a one-way ticket and $193 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 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.

See more FAQs

Top tips for finding a cheap flight from DAL to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $158 or less one-way.

Prefer to fly non-stop from Dallas Love Field to Chicago Midway Airport?

Find which airlines fly direct from Love Field to Midway, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

Top airlines flying from Love Field to Midway

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
75food
86crew
82boarding
80entertainment
81overall
79comfort
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

I love the free wifi and headrest screens. I would consider Delta even more because of this but the seats aren't so great. The snacks aren't very good in my opinion. I bought a Bloody Mary and that was great! So just be comfortable with better snacks and the airline world will be yours.

Lisa the flight attendent was absolutely wonderful - I loved her energy and you could tell that this crew was amazing family - thank you for making our flight home to LA so very fun! Love and Sun Chips!

the entertainment for the flight from DAL-LGA was not available.

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Plane was clean but they do not allow bag drop until 1 hour before flight. Just encouraging late fees and other issues. The worst I have experienced. Total hostage situation, pay or you miss your flight.

Everything was good, and most importantly on time. They have been extremely tardy in some of my flights

I had to cancel within 1hour of the reservation an they put you through hell to . no live customer service desk. I'm handy caped and they make it almost impossible to cancel. They are steeling my money. You should not have that airline on your site. Contact me and I will give you all info. Of what the are doing to me just notable treatment they are set up like that to take people

Horrible flight, rude crew, someone had so mu h perfume on breathing was difficult.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Smooth process and flight. My favorite kind. Uneventful and on-time!

Frontier is a mess. Kept changing flights and times on me. Ridiculous. Charged us twice for annual Discout Den membership.

Why are you charged for everything possible?? I went to my flight 2hours early so I can get some food.. I went to the agent to ask them to check me in and print out boarding pass.. I was told they charge for that. What in the world is that about? I understand if I’m trying to check in over the phone yes by all means charge for service.. if I’m rite there at the building asking to get checked in and get charged for it, that’s uncalled for and asking for more money at every given possibility

Flight delayed an hour. The turbulence was insane. Packed in like sardines. A coke was $4.95 no snack or a drink crazy

Book cheap flights from Dallas to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Dallas to Chicago found on KAYAK in the last 72 hours.
4/11Thu
nonstopSouthwest
2h 10mDAL-MDW
$151
4/11Thu
1 stopSouthwest
4h 20mDAL-MDW
$172
4/10Wed
nonstopSouthwest
2h 10mDAL-MDW
$179
5/29Wed
1 stopDelta
7h 50mDAL-MDW
$213
4/24Wed
1 stopDelta
5h 55mDAL-MDW
$219
4/11Thu
2 stopsSouthwest
6h 50mDAL-MDW
$238
5/12Sun
1 stopDelta
5h 52mDAL-MDW
$266
4/3Wed
1 stopDelta
5h 03mDAL-MDW
$303
4/18Thu
1 stopDelta
4h 39mDAL-MDW
$321
4/10Wed
2 stopsSouthwest
9h 15mDAL-MDW
$377

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Last minute flights from Love Field to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Dallas to Chicago that are departing in the next 10 days.
3/29Fri
multi-stopDelta
6h 00mDAL-MDW
3/31Sun
multi-stopDelta
5h 21mMDW-DAL
$682
3/29Fri
multi-stopDelta
6h 00mDAL-MDW
3/31Sun
multi-stopDelta
5h 03mMDW-DAL
$716
4/2Tue
multi-stopDelta
5h 03mDAL-MDW
4/5Fri
multi-stopDelta
5h 05mMDW-DAL
$842
4/1Mon
multi-stopDelta
5h 59mDAL-MDW
4/6Sat
multi-stopDelta
5h 19mMDW-DAL
$896
3/29Fri
multi-stopDelta
6h 00mDAL-MDW
3/31Sun
multi-stopDelta
8h 30mMDW-DAL
$1,163
3/29Fri
multi-stopDelta
6h 00mDAL-MDW
3/31Sun
multi-stopDelta
8h 30mMDW-DAL
$1,241
3/29Fri
multi-stopDelta
10h 16mDAL-MDW
3/31Sun
multi-stopDelta
8h 30mMDW-DAL
$1,805

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Dallas Love Field - Chicago Midway Airport Flights

Departure:

Dallas Love Field (DAL)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Dallas Love Field

Cabin classes:

$252