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DAL - MDW

$166 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 7/2. 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 7/6
Sat 7/13

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 44,060,346 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
3:47 pm - 11:49 pmMDW-DAL
8h 02m1 stop
$176Delta
Find Deal
Sat, Aug 17 - Tue, Aug 20
4:32 pm - 9:46 pmDAL-MDW
5h 14m1 stop
6:55 pm - 11:49 pmMDW-DAL
4h 54m1 stop
$206Delta
Find Deal
Mon, Jul 29 - Tue, Aug 6
7:29 am - 2:55 pmDAL-MDW
7h 26m1 stop
6:00 am - 11:10 amMDW-DAL
5h 10m1 stop
$212Delta
Find Deal
Mon, Jul 1 - Wed, Jul 10
10:14 am - 2:57 pmDAL-MDW
4h 43m1 stop
6:55 pm - 11:49 pmMDW-DAL
4h 54m1 stop
$222Delta
Find Deal
Tue, Aug 6 - Tue, Aug 13
2:37 pm - 9:46 pmDAL-MDW
7h 09m1 stop
6:00 am - 11:10 amMDW-DAL
5h 10m1 stop
$254Delta
Find Deal
Tue, Jul 2 - Wed, Jul 10
2:50 pm - 9:46 pmDAL-MDW
6h 56m1 stop
6:00 am - 1:22 pmMDW-DAL
7h 22m1 stop
$256Delta
Find Deal
Wed, Aug 14 - Sat, Aug 17
4:32 pm - 9:46 pmDAL-MDW
5h 14m1 stop
6:55 pm - 11:49 pmMDW-DAL
4h 54m1 stop
$268Delta
Find Deal
Wed, Jul 10 - Tue, Jul 16
7:30 am - 2:57 pmDAL-MDW
7h 27m1 stop
12:35 pm - 7:39 pmMDW-DAL
7h 04m1 stop
$274Delta
Find Deal
Sat, Jul 13 - Sat, Jul 20
10:20 pm - 12:30 amDAL-MDW
2h 10mnonstop
8:15 pm - 10:25 pmMDW-DAL
2h 10mnonstop
$276Southwest
Find Deal
Thu, Jun 20 - Fri, Jun 21
4:55 pm - 9:45 pmDAL-MDW
4h 50m1 stop
5:40 am - 7:55 amMDW-DAL
2h 15mnonstop
$280Southwest
Find Deal
Sun, Jul 14 - Fri, Jul 19

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 $199 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.

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 Delta ($166) and Southwest ($260). The cheapest round-trip tickets were found on Delta ($176) and Southwest ($276).

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

Each day, there are between 5 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 13m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 67 flights. The most frequent day of departure is Friday, when 19% 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.

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

$166
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 21% 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 $166 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 10371 reviews
8.2Boarding
7.4Food
8.0Entertainment
8.6Crew
7.9Comfort
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

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.

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

FRONTIER SUCKS! The agent downstairs tricked me into booking, just to get to the gate. At the gate, they told me they couldn't help. I then called Customer Service. They and the gate attendants kept blaming each other. Neither side was willing to help the customer.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

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

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

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.
7/2Tue
1 stopDelta
7h 09mDAL-MDW
$166
8/7Wed
1 stopDelta
4h 43mDAL-MDW
$168
7/4Thu
1 stopDelta
7h 09mDAL-MDW
$169
7/5Fri
1 stopDelta
7h 09mDAL-MDW
$178
8/4Sun
1 stopDelta
5h 44mDAL-MDW
$218
6/11Tue
1 stopDelta
5h 55mDAL-MDW
$229
6/10Mon
nonstopSouthwest
2h 15mDAL-MDW
$260
6/10Mon
1 stopSouthwest
4h 00mDAL-MDW
$264
6/19Wed
1 stopDelta
5h 08mDAL-MDW
$286
6/12Wed
1 stopDelta
5h 55mDAL-MDW
$289

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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.
6/8Sat
multi-stopDelta
5h 55mDAL-MDW
6/15Sat
multi-stopDelta
8h 11mMDW-DAL
$501
6/8Sat
multi-stopDelta
7h 11mDAL-MDW
6/15Sat
multi-stopDelta
8h 11mMDW-DAL
$572
6/10Mon
multi-stopDelta
7h 09mDAL-MDW
6/17Mon
multi-stopDelta
5h 07mMDW-DAL
$627
6/8Sat
multi-stopDelta
7h 11mDAL-MDW
6/10Mon
multi-stopDelta
5h 07mMDW-DAL
$716
6/7Fri
multi-stopDelta
7h 09mDAL-MDW
6/9Sun
multi-stopDelta
5h 03mMDW-DAL
$796
6/7Fri
multi-stopDelta
5h 08mDAL-MDW
6/10Mon
multi-stopDelta
5h 07mMDW-DAL
$797
6/10Mon
multi-stopDelta
5h 08mDAL-MDW
6/13Thu
multi-stopDelta
7h 07mMDW-DAL
$812
6/8Sat
multi-stopDelta
6h 40mDAL-MDW
6/15Sat
multi-stopDelta
7h 07mMDW-DAL
$864
6/8Sat
multi-stopDelta
7h 11mDAL-MDW
6/15Sat
multi-stopDelta
10h 17mMDW-DAL
$876
6/7Fri
multi-stopDelta
5h 08mDAL-MDW
6/9Sun
multi-stopDelta
7h 07mMDW-DAL
$878

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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