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Cheap flights from Chicago Midway Airport to Dallas from $121

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Dallas

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:20 pm - 8:50 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
Southwest Logo
8:25 pm - 10:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
$199Southwest
Sat, Dec 12 - Wed, Dec 16
Southwest Logo
6:20 pm - 8:50 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
Southwest Logo
8:35 am - 12:25 pmDAL  Dallas Love Field-MDW Chicago Midway
3h 50m1 stop Omaha Eppley Airfield
$205Southwest
Sat, Dec 12 - Tue, Dec 15
Southwest Logo
3:45 pm - 8:00 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 15m1 stop Omaha Eppley Airfield
Southwest Logo
3:00 pm - 5:10 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 10mnonstop
$205Southwest
Wed, Dec 9 - Wed, Dec 16
Southwest Logo
6:00 am - 8:35 amMDW  Chicago Midway-DAL Dallas Love Field
2h 35mnonstop
Southwest Logo
8:35 am - 12:25 pmDAL  Dallas Love Field-MDW Chicago Midway
3h 50m1 stop Omaha Eppley Airfield
$205Southwest
Sat, Dec 12 - Wed, Dec 16
Southwest Logo
8:45 pm - 11:15 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
Southwest Logo
8:35 am - 12:25 pmDAL  Dallas Love Field-MDW Chicago Midway
3h 50m1 stop Omaha Eppley Airfield
$205Southwest
Tue, Dec 1 - Tue, Dec 8
Southwest Logo
3:45 pm - 8:00 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 15m1 stop Omaha Eppley Airfield
Southwest Logo
5:35 pm - 7:50 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
$205Southwest
Wed, Dec 2 - Sat, Dec 5
Southwest Logo
6:20 pm - 8:50 pmMDW  Chicago Midway-DAL Dallas Love Field
2h 30mnonstop
Southwest Logo
8:35 am - 12:25 pmDAL  Dallas Love Field-MDW Chicago Midway
3h 50m1 stop Omaha Eppley Airfield
$205Southwest
Sat, Dec 12 - Tue, Dec 15
Southwest Logo
3:45 pm - 8:00 pmMDW  Chicago Midway-DAL Dallas Love Field
4h 15m1 stop Omaha Eppley Airfield
Southwest Logo
8:25 pm - 10:40 pmDAL  Dallas Love Field-MDW Chicago Midway
2h 15mnonstop
$205Southwest
Wed, Dec 2 - Wed, Dec 9
Delta Logo
1:02 pm - 6:09 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:12 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 52m1 stop Atlanta Hartsfield-Jackson
$219Delta
Wed, Dec 2 - Wed, Dec 9
Delta Logo
1:02 pm - 6:09 pmMDW  Chicago Midway-DAL Dallas Love Field
5h 07m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:12 am - 12:04 pmDAL  Dallas Love Field-MDW Chicago Midway
5h 52m1 stop Atlanta Hartsfield-Jackson
$219Delta
Wed, Dec 2 - Tue, Dec 8

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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
Dec 12
MDW6:20 pmChicago Midway
2h 30m
DAL8:50 pmDallas Love Field
Dec 16
DAL8:25 pmDallas Love Field
2h 15m
MDW10:40 pmChicago Midway
$199
Southwest
Dec 12
MDW6:00 amChicago Midway
2h 35m
DAL8:35 amDallas Love Field
Dec 16
DAL8:35 amDallas Love Field
3h 50m
1 stop
MDW12:25 pmChicago Midway
$205
Southwest
Dec 5
MDW7:50 amChicago Midway
4h 55m
1 stop
DAL12:45 pmDallas Love Field
Dec 12
DAL5:35 pmDallas Love Field
2h 15m
MDW7:50 pmChicago Midway
$209

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
Dec 2
MDW1:02 pmChicago Midway
5h 07m
1 stop
DAL6:09 pmDallas Love Field
Dec 9
DAL6:12 amDallas Love Field
5h 52m
1 stop
MDW12:04 pmChicago Midway
$219
Delta
Dec 5
MDW6:00 amChicago Midway
8h 17m
1 stop
DAL2:17 pmDallas Love Field
Dec 8
DAL6:12 amDallas Love Field
10h 38m
2 stops
MDW4:50 pmChicago Midway
$224
Delta
Dec 5
MDW10:24 amChicago Midway
12h 19m
2 stops
DAL10:43 pmDallas Love Field
Dec 8
DAL6:12 amDallas Love Field
10h 38m
2 stops
MDW4:50 pmChicago Midway
$229

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Dallas Love Field Airport that are best for you.

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Price

Cheapest round-trip
Quickest round-trip

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Sat 12/12

6:20 pm-8:50 pm

Nonstop2h 30m

Dallas Love Field

Wed 12/16

8:25 pm-10:40 pm

Nonstop2h 15m

$199

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Sat 12/12

6:20 pm-8:50 pm

Nonstop2h 30m

Dallas Love Field

Tue 12/15

8:35 am-12:25 pm

1 stop3h 50m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Wed 12/9

3:45 pm-8:00 pm

1 stop4h 15m

Dallas Love Field

Wed 12/16

3:00 pm-5:10 pm

Nonstop2h 10m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Sat 12/12

6:00 am-8:35 am

Nonstop2h 35m

Dallas Love Field

Wed 12/16

8:35 am-12:25 pm

1 stop3h 50m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Tue 12/1

8:45 pm-11:15 pm

Nonstop2h 30m

Dallas Love Field

Tue 12/8

8:35 am-12:25 pm

1 stop3h 50m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Wed 12/2

3:45 pm-8:00 pm

1 stop4h 15m

Dallas Love Field

Sat 12/5

5:35 pm-7:50 pm

Nonstop2h 15m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Sat 12/12

6:20 pm-8:50 pm

Nonstop2h 30m

Dallas Love Field

Tue 12/15

8:35 am-12:25 pm

1 stop3h 50m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Wed 12/2

3:45 pm-8:00 pm

1 stop4h 15m

Dallas Love Field

Wed 12/9

8:25 pm-10:40 pm

Nonstop2h 15m

$205

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Wed 12/2

1:02 pm-6:09 pm

1 stop5h 07m

Dallas Love Field

Wed 12/9

6:12 am-12:04 pm

1 stop5h 52m

$219

ChicagoDallas

MDW Chicago Midway - DAL Dallas Love Field

MDWDAL

Chicago Midway

Wed 12/2

1:02 pm-6:09 pm

1 stop5h 07m

Dallas Love Field

Tue 12/8

6:12 am-12:04 pm

1 stop5h 52m

$219

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 typical price of a round-trip flight between Chicago Midway Airport and Dallas Love Field Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $394 to $608.
The lowest price recently found on this route was $199.

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 January, then flying in February is also cheap. Prices for this month can be found on momondo for an average of $357.

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

According to our data, Thursday is the cheapest day to fly to Dallas Love Field Airport from Chicago Midway Airport. The lowest ticket price found for a Thursday departure recently was $322. 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 $515.

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

At noon 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 $336. Flying to Dallas Love Field Airport at noon 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 $420 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

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

You are more likely to see cheaper flights to Dallas Love Field Airport from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Dallas Love Field Airport for around $433 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Dallas Love Field Airport from Chicago Midway Airport for as low as $235 on momondo.

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

There is only 1 cabin class available to choose from on Chicago Midway Airport to Dallas Love Field Airport 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?

You could potentially save up to 7% on your flight if you consider stops on a Chicago Midway Airport to Dallas Love Field Airport flight.

How have Chicago Midway Airport to Dallas Love Field Airport flight prices changed over time?

As of November 2026, prices for Chicago Midway Airport to Dallas Love Field Airport flights are approximately 23% cheaper when compared to flights at the same time last year.

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

$121

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Dallas Love Field Airport from Chicago Midway Airport in the past 72 hours is $121. The best round-trip flight deal from Chicago Midway Airport to Dallas Love Field Airport found on momondo in the last 72 hours is $199.
The fastest flight from Chicago Midway Airport to Dallas Love Field Airport takes 2h 15m
Direct flights go from Chicago Midway Airport to Dallas Love Field Airport every day.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Dallas Love Field Airport

  • 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
SouthwestPriceFrom $223Free CancellationRating
8.0
4,215 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 29 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Dallas Love Field Airport starts from $223 round-trip, up to an average price of $439. 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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