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Cheap flights from Chicago Midway Airport to Dallas from $100

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 5/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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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
5:30 am - 7:55 am
MDW
-
DAL
2h 25mnonstop
Southwest Logo
3:15 pm - 5:30 pm
DAL
-
MDW
2h 15mnonstop
$199Southwest
Thu, Apr 30 - Sat, May 2
Southwest Logo
3:05 pm - 5:30 pm
MDW
-
DAL
2h 25mnonstop
Southwest Logo
2:10 pm - 6:00 pm
DAL
-
MDW
3h 50m
1 stop
$205Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
12:45 pm - 5:55 pm
MDW
-
DAL
5h 10m
1 stop
Southwest Logo
7:05 pm - 9:15 pm
DAL
-
MDW
2h 10mnonstop
$209Southwest
Thu, Apr 30 - Mon, May 4
Southwest Logo
10:30 am - 2:25 pm
MDW
-
DAL
3h 55m
1 stop
Southwest Logo
11:00 am - 2:55 pm
DAL
-
MDW
3h 55m
1 stop
$210Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
12:45 pm - 5:55 pm
MDW
-
DAL
5h 10m
1 stop
Southwest Logo
12:40 pm - 4:50 pm
DAL
-
MDW
4h 10m
1 stop
$214Southwest
Thu, Apr 30 - Sat, May 2
Southwest Logo
8:10 am - 2:45 pm
MDW
-
DAL
6h 35m
2 stops
Southwest Logo
11:00 am - 2:55 pm
DAL
-
MDW
3h 55m
1 stop
$215Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
5:05 am - 7:20 am
MDW
-
DAL
2h 15mnonstop
Southwest Logo
9:55 pm - 12:05 am
DAL
-
MDW
2h 10mnonstop
$217Southwest
Wed, Jun 17 - Wed, Jun 24
Southwest Logo
4:00 pm - 9:00 pm
MDW
-
DAL
5h 00m
1 stop
Southwest Logo
12:05 pm - 5:15 pm
DAL
-
MDW
5h 10m
1 stop
$219Southwest
Thu, Apr 30 - Mon, May 4
Southwest Logo
10:00 am - 4:00 pm
MDW
-
DAL
6h 00m
2 stops
Southwest Logo
11:00 am - 2:55 pm
DAL
-
MDW
3h 55m
1 stop
$220Southwest
Sat, May 9 - Mon, May 11
Southwest Logo
5:00 pm - 7:30 pm
MDW
-
DAL
2h 30mnonstop
Southwest Logo
7:05 pm - 9:15 pm
DAL
-
MDW
2h 10mnonstop
$221Southwest
Thu, May 14 - Mon, May 18

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
Apr 30
MDW5:30 amChicago Midway
2h 25m
DAL7:55 amDallas Love Field
May 2
DAL3:15 pmDallas Love Field
2h 15m
MDW5:30 pmChicago Midway
$199
Southwest
May 9
MDW10:30 amChicago Midway
3h 55m
1 stop
DAL2:25 pmDallas Love Field
May 12
DAL6:05 pmDallas Love Field
2h 15m
MDW8:20 pmChicago Midway
$205
Southwest
Apr 30
MDW12:45 pmChicago Midway
5h 10m
1 stop
DAL5:55 pmDallas Love Field
May 4
DAL7:05 pmDallas Love Field
2h 10m
MDW9:15 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
May 1
MDW5:21 pmChicago Midway
5h 12m
1 stop
DAL10:33 pmDallas Love Field
May 2
DAL10:17 amDallas Love Field
6h 09m
1 stop
MDW4:26 pmChicago Midway
$253
Delta
May 12
MDW5:10 pmChicago Midway
6h 46m
1 stop
DAL11:56 pmDallas Love Field
Oct 3
DAL3:45 pmDallas Love Field
6h 01m
1 stop
MDW9:46 pmChicago Midway
$262
Delta
Apr 14
MDW5:21 pmChicago Midway
5h 12m
1 stop
DAL10:33 pmDallas Love Field
May 2
DAL10:17 amDallas Love Field
6h 09m
1 stop
MDW4:26 pmChicago Midway
$307

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 April 10, 2026.
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

Cheapest round-trip

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 4/30

5:30 am-7:55 am

Nonstop2h 25m

Dallas Love Field

Sat 5/2

3:15 pm-5:30 pm

Nonstop2h 15m

$199

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 5/9

3:05 pm-5:30 pm

Nonstop2h 25m

Dallas Love Field

Mon 5/11

2:10 pm-6:00 pm

1 stop3h 50m

$205

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 4/30

12:45 pm-5:55 pm

1 stop5h 10m

Dallas Love Field

Mon 5/4

7:05 pm-9:15 pm

Nonstop2h 10m

$209

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 5/9

10:30 am-2:25 pm

1 stop3h 55m

Dallas Love Field

Mon 5/11

11:00 am-2:55 pm

1 stop3h 55m

$210

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 4/30

12:45 pm-5:55 pm

1 stop5h 10m

Dallas Love Field

Sat 5/2

12:40 pm-4:50 pm

1 stop4h 10m

$214

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 5/9

8:10 am-2:45 pm

2 stops6h 35m

Dallas Love Field

Mon 5/11

11:00 am-2:55 pm

1 stop3h 55m

$215
Quickest round-trip

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 6/17

5:05 am-7:20 am

Nonstop2h 15m

Dallas Love Field

Wed 6/24

9:55 pm-12:05 am

Nonstop2h 10m

$217

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 4/30

4:00 pm-9:00 pm

1 stop5h 00m

Dallas Love Field

Mon 5/4

12:05 pm-5:15 pm

1 stop5h 10m

$219

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 5/9

10:00 am-4:00 pm

2 stops6h 00m

Dallas Love Field

Mon 5/11

11:00 am-2:55 pm

1 stop3h 55m

$220

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 5/14

5:00 pm-7:30 pm

Nonstop2h 30m

Dallas Love Field

Mon 5/18

7:05 pm-9:15 pm

Nonstop2h 10m

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

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 September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $249.

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 $255. 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 $391.

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 $238. 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 $293 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.

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

As of April 2026, prices for Chicago Midway Airport to Dallas Love Field Airport flights are approximately 24% 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

$170

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 $170. The best round-trip flight deal from Chicago Midway Airport to Dallas Love Field Airport found on momondo in the last 72 hours is $260.
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

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 10m, 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 $160Free CancellationRating
8.0
4,334 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 $160 round-trip, up to an average price of $323. 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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