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Cheap flights from Chicago Midway Airport to Dallas from $79

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Dallas departing on 11/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago Midway Airport to Dallas

Cheap round-trip flights

Southwest Logo
5:45 am - 8:00 amMDW-DAL
2h 15mnonstop
Southwest Logo
6:05 pm - 8:20 pmDAL-MDW
2h 15mnonstop
$157Southwest
Find Deal
Sat, Oct 25 - Sat, Oct 25
Southwest Logo
12:55 pm - 5:00 pmMDW-DAL
4h 05m1 stop
Southwest Logo
9:55 pm - 12:05 amDAL-MDW
2h 10mnonstop
$163Southwest
Find Deal
Sat, Oct 25 - Mon, Oct 27
Southwest Logo
12:50 pm - 6:05 pmMDW-DAL
5h 15m1 stop
Southwest Logo
9:55 pm - 12:05 amDAL-MDW
2h 10mnonstop
$167Southwest
Find Deal
Sat, Oct 18 - Mon, Oct 20
Southwest Logo
6:55 am - 9:10 amMDW-DAL
2h 15mnonstop
Southwest Logo
6:45 am - 8:55 amDAL-MDW
2h 10mnonstop
$168Southwest
Find Deal
Fri, Oct 31 - Mon, Nov 3
Southwest Logo
12:55 pm - 5:00 pmMDW-DAL
4h 05m1 stop
Southwest Logo
6:55 pm - 12:25 amDAL-MDW
5h 30m1 stop
$172Southwest
Find Deal
Sat, Oct 25 - Mon, Oct 27
Southwest Logo
8:25 am - 12:05 pmMDW-DAL
3h 40m1 stop
Southwest Logo
6:45 am - 8:55 amDAL-MDW
2h 10mnonstop
$174Southwest
Find Deal
Fri, Oct 31 - Mon, Nov 3
Southwest Logo
10:10 am - 2:55 pmMDW-DAL
4h 45m1 stop
Southwest Logo
3:20 pm - 7:05 pmDAL-MDW
3h 45m1 stop
$177Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
5:35 am - 7:50 amMDW-DAL
2h 15mnonstop
Southwest Logo
12:25 pm - 5:05 pmDAL-MDW
4h 40m1 stop
$178Southwest
Find Deal
Fri, Oct 31 - Mon, Nov 3
Delta Logo
5:34 pm - 11:58 pmMDW-DAL
6h 24m1 stop
Delta Logo
6:40 pm - 11:32 pmDAL-MDW
4h 52m1 stop
$207Delta
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Fri, Nov 14 - Sat, Nov 15
Delta Logo
12:47 pm - 5:50 pmMDW-DAL
5h 03m1 stop
Delta Logo
6:00 am - 11:55 amDAL-MDW
5h 55m1 stop
$221Delta
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Sun, Nov 23 - Tue, Dec 2

Southwest flights from Chicago Midway Airport to Dallas Love Field Airport

Our best Southwest deals on Chicago Midway Airport to Dallas Love Field Airport flight tickets
Southwest
Oct 25
MDW5:45 amChicago Midway
2h 15m
DAL8:00 amDallas Love Field
Oct 25
DAL6:05 pmDallas Love Field
2h 15m
MDW8:20 pmChicago Midway
$157
Find similar
Southwest
Oct 25
MDW12:55 pmChicago Midway
4h 05m
1 stop
DAL5:00 pmDallas Love Field
Oct 27
DAL9:55 pmDallas Love Field
2h 10m
MDW12:05 amChicago Midway
$163
Find similar
Southwest
Oct 18
MDW12:50 pmChicago Midway
5h 15m
1 stop
DAL6:05 pmDallas Love Field
Oct 20
DAL9:55 pmDallas Love Field
2h 10m
MDW12:05 amChicago Midway
$167
Find similar

Delta flights from Chicago Midway Airport to Dallas Love Field Airport

Our best Delta deals on Chicago Midway Airport to Dallas Love Field Airport flight tickets
Delta
Nov 14
MDW5:34 pmChicago Midway
6h 24m
1 stop
DAL11:58 pmDallas Love Field
Nov 15
DAL6:40 pmDallas Love Field
4h 52m
1 stop
MDW11:32 pmChicago Midway
$207
Find similar
Delta
Nov 23
MDW12:47 pmChicago Midway
5h 03m
1 stop
DAL5:50 pmDallas Love Field
Dec 2
DAL6:00 amDallas Love Field
5h 55m
1 stop
MDW11:55 amChicago Midway
$221
Find similar
Delta
Oct 7
MDW6:00 amChicago Midway
7h 29m
1 stop
DAL1:29 pmDallas Love Field
Oct 11
DAL8:42 amDallas Love Field
6h 44m
1 stop
MDW3:26 pmChicago Midway
$234
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Dallas Love Field Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Dallas Love Field Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 10/25

5:45 am-8:00 am

Nonstop2h 15m

Dallas Love Field

Sat 10/25

6:05 pm-8:20 pm

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 10/25

12:55 pm-5:00 pm

1 stop4h 05m

Dallas Love Field

Mon 10/27

9:55 pm-12:05 am

Nonstop2h 10m

$163

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 10/18

12:50 pm-6:05 pm

1 stop5h 15m

Dallas Love Field

Mon 10/20

9:55 pm-12:05 am

Nonstop2h 10m

$167

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Fri 10/31

6:55 am-9:10 am

Nonstop2h 15m

Dallas Love Field

Mon 11/3

6:45 am-8:55 am

Nonstop2h 10m

$168

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 10/25

12:55 pm-5:00 pm

1 stop4h 05m

Dallas Love Field

Mon 10/27

6:55 pm-12:25 am

1 stop5h 30m

$172

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Fri 10/31

8:25 am-12:05 pm

1 stop3h 40m

Dallas Love Field

Mon 11/3

6:45 am-8:55 am

Nonstop2h 10m

$174

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/15

10:10 am-2:55 pm

1 stop4h 45m

Dallas Love Field

Sat 10/18

3:20 pm-7:05 pm

1 stop3h 45m

$177

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Fri 10/31

5:35 am-7:50 am

Nonstop2h 15m

Dallas Love Field

Mon 11/3

12:25 pm-5:05 pm

1 stop4h 40m

$178

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Fri 11/14

5:34 pm-11:58 pm

1 stop6h 24m

Dallas Love Field

Sat 11/15

6:40 pm-11:32 pm

1 stop4h 52m

$207

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sun 11/23

12:47 pm-5:50 pm

1 stop5h 03m

Dallas Love Field

Tue 12/2

6:00 am-11:55 am

1 stop5h 55m

$221

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Dallas from

How to get the cheapest flight ticket from Chicago Midway Airport to Dallas Love Field Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Dallas Love Field Airport?

If you aren’t able to travel to Dallas Love Field Airport during the month of April, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $206.

What is the cheapest day to depart on your flight to Dallas Love Field Airport?

According to our data, Wednesday is the cheapest day to fly to Dallas Love Field Airport from Chicago Midway Airport. The lowest ticket price found for a Wednesday departure recently was $256. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to Dallas Love Field Airport is Sunday, with ticket prices averaging around $383.

What is the cheapest time of day to depart on your flight to Dallas Love Field Airport?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to Dallas Love Field Airport when you can find flight prices for as low as $229. Flying to Dallas Love Field Airport in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Dallas Love Field Airport, so prices are often more expensive at around $307 per ticket.

What is the cheapest Chicago Midway to Dallas Love Field flight route?

Fly from Chicago Midway to Dallas Love Field for the best Chicago Midway - Dallas Love Field flight prices

What cabin class options are available on Chicago Midway to Dallas Love Field flights?

There is only 1 cabin class available to choose from on Chicago Midway to Dallas Love Field flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago Midway Airport to Dallas Love Field Airport flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Dallas Love Field Airport.

When to book flights from Chicago Midway Airport to Dallas Love Field Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Dallas Love Field Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Dallas Love Field Airport (MDW to DAL) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Dallas Love Field Airport

Best Price Found

$178

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Dallas Love Field Airport from Chicago Midway Airport in the past 72 hours is $178. The best round-trip flight deal from Chicago Midway Airport to Dallas Love Field Airport found on momondo in the last 72 hours is $187.
The fastest flight from Chicago Midway Airport to Dallas Love Field Airport takes 2h 10m
Direct flights go from Chicago Midway Airport to Dallas Love Field Airport every day.
Search flight deals

  • How far is Chicago Midway to Dallas Love Field by plane?

    The straight-line distance from Chicago Midway to Dallas Love Field is 793.4 mi. Flights usually cover this in 2h 15m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago Midway Airport to Dallas Love Field Airport?

    Prices for flights from Chicago Midway Airport to Dallas Love Field Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to Dallas Love Field Airport?

  • How old do you have to be to fly from Chicago Midway Airport to Dallas Love Field Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Dallas Love Field Airport.

  • What documentation or ID do you need to fly to Dallas Love Field Airport?

    The travel and health documents you'll need for your trip to Dallas Love Field Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Dallas Love Field Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Dallas Love Field Airport?

  • What is the most popular airline from Chicago Midway Airport to Dallas Love Field Airport?

Best airlines flying from Chicago Midway Airport to Dallas Love Field Airport

Compare and see reviews for airlines that fly from Chicago Midway Airport to Dallas Love Field Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $86Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to Dallas Love Field Airport

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Dallas Love Field Airport, operating 46 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Dallas Love Field Airport starts from $157 round-trip, up to an average price of $289. Our users have rated Southwest at 8.0/10.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Dallas?

It is quick and easy to find Chicago to Dallas flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Dallas that suits you.

Can I find flights from Chicago to Dallas with flexible booking policies on momondo?

Flights from Chicago to Dallas with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Dallas?

Once all potential Chicago to Dallas flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Dallas right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Dallas now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Dallas and let you know when they change.

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