Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

DAL - MDW

Find cheap flights from Dallas Love Field to Chicago Midway Airport from $98

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 6/11. 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
Fri 6/7
Fri 6/14

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 43,968,530 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
4:24 pm - 9:41 pmDAL-MDW
5h 17m1 stop
6:00 am - 2:00 pmMDW-DAL
8h 00m1 stop
$208Delta
Find Deal
Tue, Jul 9 - Sat, Jul 13
4:24 pm - 9:41 pmDAL-MDW
5h 17m1 stop
1:05 pm - 7:45 pmMDW-DAL
6h 40m1 stop
$218Delta
Find Deal
Mon, Jul 15 - Sat, Jul 20
6:30 pm - 8:40 pmDAL-MDW
2h 10mnonstop
8:30 pm - 7:15 amMDW-DAL
10h 45m1 stop
$267Southwest
Find Deal
Tue, May 21 - Wed, May 22
4:24 pm - 9:41 pmDAL-MDW
5h 17m1 stop
6:49 pm - 11:56 pmMDW-DAL
5h 07m1 stop
$268Delta
Find Deal
Tue, Jul 9 - Tue, Jul 16
10:30 am - 10:00 pmDAL-MDW
11h 30m1 stop
8:30 pm - 7:15 amMDW-DAL
10h 45m1 stop
$269Southwest
Find Deal
Tue, May 21 - Wed, May 22
9:10 pm - 11:20 pmDAL-MDW
2h 10mnonstop
8:25 am - 10:45 amMDW-DAL
2h 20mnonstop
$271Southwest
Find Deal
Tue, May 21 - Wed, May 22
12:01 pm - 5:59 pmDAL-MDW
5h 58m1 stop
10:11 am - 5:03 pmMDW-DAL
6h 52m1 stop
$273Delta
Find Deal
Fri, Aug 16 - Thu, Aug 22
2:50 pm - 9:47 pmDAL-MDW
6h 57m1 stop
6:00 am - 1:55 pmMDW-DAL
7h 55m1 stop
$287Delta
Find Deal
Thu, Aug 29 - Sun, Sep 1
4:24 pm - 9:41 pmDAL-MDW
5h 17m1 stop
3:45 pm - 11:56 pmMDW-DAL
8h 11m1 stop
$328Delta
Find Deal
Wed, Jul 10 - Wed, Jul 17
2:50 pm - 9:41 pmDAL-MDW
6h 51m1 stop
6:50 pm - 11:41 pmMDW-DAL
4h 51m1 stop
$337Delta
Find Deal
Sat, Aug 3 - Fri, Aug 9

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 October, where tickets cost $94 on average. On the other hand, the most expensive months are July and November, where the average cost of tickets is $215 and $188 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 53 days before departure.

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

Each day, there are between 7 and 14 nonstop flights that take off from Dallas Love Field Airport and land in Chicago Midway Airport, with an average flight time of 2h 12m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 86 flights. The most frequent day of departure is Monday, when 16% of all weekly flights depart. The fewest flights depart on a Sunday.

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 8:15 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 10:20 pm and lands at 12:30 am.

Good to know

Low season

February

High season

March

Cheapest flight

$98
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 18% 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 $98 for a one-way ticket and $208 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?

    Only American Airlines offers 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 737-800 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

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

 
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
DeltaOverall score based on 10789 reviews
7.9Comfort
8.6Crew
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

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

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

I paid for extra leg room. The flimsy plastic seat underneath the floatation seat did not line up with the arm rests. It seemed as if the plastic part was zip tied on but immovable. This caused severe uncomfortable for the duration of the flight.

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

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.
6/11Tue
1 stopDelta
5h 08mDAL-MDW
$98
5/14Tue
1 stopDelta
6h 10mDAL-MDW
$129
6/10Mon
1 stopDelta
7h 09mDAL-MDW
$169
6/13Thu
1 stopDelta
5h 55mDAL-MDW
$218
5/15Wed
1 stopDelta
7h 50mDAL-MDW
$219
5/15Wed
1 stopDelta
7h 50mDAL-MDW
$220
5/14Tue
1 stopDelta
6h 10mDAL-MDW
$229
5/29Wed
1 stopDelta
6h 10mDAL-MDW
$258
5/18Sat
1 stopDelta
5h 31mDAL-MDW
$259
5/28Tue
1 stopDelta
5h 32mDAL-MDW
$298

Search by stops

Search by airline

Search by price

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.
5/11Sat
multi-stopDelta
6h 55mDAL-MDW
5/14Tue
multi-stopDelta
6h 16mMDW-DAL
$279
5/13Mon
nonstopSouthwest
2h 10mDAL-MDW
5/14Tue
multi-stopSouthwest
4h 05mMDW-DAL
$341
5/13Mon
nonstopSouthwest
2h 10mDAL-MDW
5/14Tue
nonstopSouthwest
2h 20mMDW-DAL
$349
5/13Mon
multi-stopSouthwest
3h 30mDAL-MDW
5/14Tue
multi-stopSouthwest
4h 05mMDW-DAL
$350
5/13Mon
multi-stopSouthwest
6h 00mDAL-MDW
5/14Tue
multi-stopSouthwest
6h 25mMDW-DAL
$355
5/13Mon
nonstopSouthwest
2h 10mDAL-MDW
5/16Thu
nonstopSouthwest
2h 15mMDW-DAL
$362
5/13Mon
nonstopSouthwest
2h 10mDAL-MDW
5/16Thu
multi-stopSouthwest
4h 20mMDW-DAL
$363
5/13Mon
nonstopSouthwest
2h 10mDAL-MDW
5/16Thu
multi-stopSouthwest
9h 45mMDW-DAL
$368
5/13Mon
multi-stopSouthwest
6h 00mDAL-MDW
5/16Thu
multi-stopSouthwest
4h 20mMDW-DAL
$377
5/10Fri
multi-stopDelta
4h 37mDAL-MDW
5/30Thu
multi-stopDelta
4h 54mMDW-DAL
$447

Search by stops

Search by airline

Search by price

Dallas Love Field - Chicago Midway Airport Flights

Departure:

Dallas Love Field (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Dallas Love Field

Cabin classes:

$1,218