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DAL - MDW

$118 Find cheap flights from Dallas Love Field to Chicago Midway Airport

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 7/27. 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
Thu 6/27
Thu 7/4

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 42,816,550 times on KAYAK, and here is why:

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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
6:00 am - 11:44 amDAL-MDW
5h 44m1 stop
10:28 am - 5:14 pmMDW-DAL
6h 46m1 stop
$176Delta
Find Deal
Sun, Sep 1 - Thu, Sep 5
7:30 am - 2:57 pmDAL-MDW
7h 27m1 stop
12:35 pm - 7:59 pmMDW-DAL
7h 24m1 stop
$196Delta
Find Deal
Tue, Aug 6 - Sat, Aug 10
4:54 pm - 9:46 pmDAL-MDW
4h 52m1 stop
6:55 pm - 11:49 pmMDW-DAL
4h 54m1 stop
$439Delta
Find Deal
Thu, Jul 4 - Mon, Jul 8
2:12 pm - 9:46 pmDAL-MDW
7h 34m1 stop
6:55 pm - 11:49 pmMDW-DAL
4h 54m1 stop
$487Delta
Find Deal
Thu, Jul 18 - Tue, Jul 23
7:29 am - 2:55 pmDAL-MDW
7h 26m1 stop
6:00 am - 1:47 pmMDW-DAL
7h 47m1 stop
$499Delta
Find Deal
Sat, Jun 15 - Sat, Jun 22
10:24 am - 5:59 pmDAL-MDW
7h 35m1 stop
12:45 pm - 5:48 pmMDW-DAL
5h 03m1 stop
$539Delta
Find Deal
Wed, Jun 26 - Sat, Jun 29
6:00 am - 11:44 amDAL-MDW
5h 44m1 stop
10:28 am - 5:14 pmMDW-DAL
6h 46m1 stop
$546Delta
Find Deal
Sun, Sep 1 - Sat, Sep 7
4:54 pm - 9:46 pmDAL-MDW
4h 52m1 stop
12:45 pm - 7:45 pmMDW-DAL
7h 00m1 stop
$579Delta
Find Deal
Thu, Jul 4 - Sat, Jul 6
7:30 am - 2:57 pmDAL-MDW
7h 27m1 stop
3:47 pm - 8:45 pmMDW-DAL
4h 58m1 stop
$611Delta
Find Deal
Fri, Jul 12 - Mon, Jul 15
7:29 am - 2:55 pmDAL-MDW
7h 26m1 stop
6:00 am - 1:47 pmMDW-DAL
7h 47m1 stop
$695Delta
Find Deal
Thu, Jun 27 - Sun, Jun 30

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 Saturday 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 $198 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 5 and 7 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 46 flights. The most frequent day of departure is Thursday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

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.

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

$118
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 23% 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 $118 for a one-way ticket and $176 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 10502 reviews
8.6Crew
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

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.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Well I mean u get what u pay for so 🤷‍♂️

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.

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.
7/27Sat
1 stopDelta
7h 34mDAL-MDW
$118
7/23Tue
1 stopDelta
7h 34mDAL-MDW
$166
7/25Thu
1 stopDelta
7h 34mDAL-MDW
$169
7/28Sun
1 stopDelta
5h 44mDAL-MDW
$218
7/21Sun
1 stopDelta
7h 27mDAL-MDW
$286
6/2Sun
1 stopDelta
5h 48mDAL-MDW
$308
6/4Tue
1 stopDelta
7h 50mDAL-MDW
$329
6/3Mon
1 stopDelta
4h 37mDAL-MDW
$409
9/29Sun
1 stopDelta
5h 19mDAL-MDW
$416
7/27Sat
2 stopsDelta
11h 04mDAL-MDW
$429

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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.
5/29Wed
multi-stopDelta
5h 32mDAL-MDW
6/3Mon
multi-stopDelta
4h 55mMDW-DAL
$943

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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:

$1,218