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Cheap flights from Chicago Midway Airport to Dallas from $141

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 5/27. 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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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
8:55 pm - 11:15 pm
MDW
-
DAL
2h 20mnonstop
Southwest Logo
6:30 pm - 8:40 pm
DAL
-
MDW
2h 10mnonstop
$281Southwest
sáb, jul 11 - qua, jul 15
Southwest Logo
10:30 am - 2:15 pm
MDW
-
DAL
3h 45m
1 stop
Southwest Logo
1:10 pm - 3:20 pm
DAL
-
MDW
2h 10mnonstop
$287Southwest
ter, ago 11 - ter, ago 18
Southwest Logo
8:50 am - 11:05 am
MDW
-
DAL
2h 15mnonstop
Southwest Logo
5:45 pm - 11:15 pm
DAL
-
MDW
5h 30m
1 stop
$291Southwest
sáb, jul 18 - sáb, jul 25
Southwest Logo
8:50 am - 2:40 pm
MDW
-
DAL
5h 50m
2 stops
Southwest Logo
6:15 am - 8:25 am
DAL
-
MDW
2h 10mnonstop
$292Southwest
ter, ago 11 - sáb, ago 15
Southwest Logo
10:20 am - 2:05 pm
MDW
-
DAL
3h 45m
1 stop
Southwest Logo
7:45 pm - 11:55 pm
DAL
-
MDW
4h 10m
1 stop
$296Southwest
qui, mai 28 - sex, mai 29
Southwest Logo
7:45 am - 11:50 am
MDW
-
DAL
4h 05m
1 stop
Southwest Logo
12:00 pm - 5:00 pm
DAL
-
MDW
5h 00m
2 stops
$297Southwest
qua, jul 8 - ter, jul 14
Southwest Logo
5:30 am - 7:55 am
MDW
-
DAL
2h 25mnonstop
Southwest Logo
9:45 pm - 11:55 pm
DAL
-
MDW
2h 10mnonstop
$300Southwest
qui, mai 28 - sex, mai 29
Southwest Logo
6:30 am - 12:50 pm
MDW
-
DAL
6h 20m
1 stop
Southwest Logo
9:55 pm - 12:05 am
DAL
-
MDW
2h 10mnonstop
$301Southwest
sáb, jul 4 - ter, jul 7
Southwest Logo
8:10 am - 5:05 pm
MDW
-
DAL
8h 55m
2 stops
Southwest Logo
4:05 pm - 6:15 pm
DAL
-
MDW
2h 10mnonstop
$302Southwest
ter, jun 30 - sáb, jul 11
Southwest Logo
6:50 am - 1:35 pm
MDW
-
DAL
6h 45m
2 stops
Southwest Logo
7:50 pm - 10:00 pm
DAL
-
MDW
2h 10mnonstop
$306Southwest
sáb, jul 4 - ter, jul 7

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
May 30
MDW7:25 amChicago Midway
2h 25m
DAL9:50 amDallas Love Field
Jun 6
DAL6:45 pmDallas Love Field
2h 15m
MDW9:00 pmChicago Midway
$276
Southwest
May 23
MDW6:15 pmChicago Midway
2h 25m
DAL8:40 pmDallas Love Field
May 27
DAL2:45 pmDallas Love Field
2h 15m
MDW5:00 pmChicago Midway
$279
Southwest
Jul 11
MDW7:00 pmChicago Midway
2h 15m
DAL9:15 pmDallas Love Field
Jul 18
DAL8:55 pmDallas Love Field
2h 10m
MDW11:05 pmChicago Midway
$281

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
Jul 4
MDW10:55 amChicago Midway
7h 00m
1 stop
DAL5:55 pmDallas Love Field
Jul 11
DAL10:07 amDallas Love Field
5h 30m
1 stop
MDW3:37 pmChicago Midway
$301
Delta
Jul 4
MDW9:17 amChicago Midway
8h 38m
2 stops
DAL5:55 pmDallas Love Field
Jul 11
DAL10:07 amDallas Love Field
5h 30m
1 stop
MDW3:37 pmChicago Midway
$306
Delta
Jul 8
MDW5:10 pmChicago Midway
5h 15m
1 stop
DAL10:25 pmDallas Love Field
Jul 12
DAL10:07 amDallas Love Field
6h 08m
1 stop
MDW4:15 pmChicago Midway
$328

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 maio 22, 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
Quickest round-trip

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

sáb 7/11

8:55 pm-11:15 pm

Nonstop2h 20m

Dallas Love Field

qua 7/15

6:30 pm-8:40 pm

Nonstop2h 10m

$281

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

ter 8/11

10:30 am-2:15 pm

1 stop3h 45m

Dallas Love Field

ter 8/18

1:10 pm-3:20 pm

Nonstop2h 10m

$287

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

sáb 7/18

8:50 am-11:05 am

Nonstop2h 15m

Dallas Love Field

sáb 7/25

5:45 pm-11:15 pm

1 stop5h 30m

$291

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

ter 8/11

8:50 am-2:40 pm

2 stops5h 50m

Dallas Love Field

sáb 8/15

6:15 am-8:25 am

Nonstop2h 10m

$292

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

qui 5/28

10:20 am-2:05 pm

1 stop3h 45m

Dallas Love Field

sex 5/29

7:45 pm-11:55 pm

1 stop4h 10m

$296

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

qua 7/8

7:45 am-11:50 am

1 stop4h 05m

Dallas Love Field

ter 7/14

12:00 pm-5:00 pm

2 stops5h 00m

$297

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

qui 5/28

5:30 am-7:55 am

Nonstop2h 25m

Dallas Love Field

sex 5/29

9:45 pm-11:55 pm

Nonstop2h 10m

$300

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

sáb 7/4

6:30 am-12:50 pm

1 stop6h 20m

Dallas Love Field

ter 7/7

9:55 pm-12:05 am

Nonstop2h 10m

$301

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

ter 6/30

8:10 am-5:05 pm

2 stops8h 55m

Dallas Love Field

sáb 7/11

4:05 pm-6:15 pm

Nonstop2h 10m

$302

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

sáb 7/4

6:50 am-1:35 pm

2 stops6h 45m

Dallas Love Field

ter 7/7

7:50 pm-10:00 pm

Nonstop2h 10m

$306

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 $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 $440.

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 $246. 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 $333 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 $326 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 $170 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 8% 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 May 2026, prices for Chicago Midway Airport to Dallas Love Field Airport flights are approximately 84% more expensive 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

$171

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 $171. The best round-trip flight deal from Chicago Midway Airport to Dallas Love Field Airport found on momondo in the last 72 hours is $356.
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 $177Free CancellationRating
7.9
4,277 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 45 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Dallas Love Field Airport starts from $177 round-trip, up to an average price of $356. Our users have rated Southwest at 7.9/10.

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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