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Cheap flights from Chicago 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 to Dallas departing on 5/24. 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 to Dallas

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:30 am - 8:50 am
MDW
-
DAL
2h 20mnonstop
Southwest Logo
6:00 am - 8:15 am
DAL
-
MDW
2h 15mnonstop
$281Southwest
Wed, Jun 24 - Sat, Jun 27
Southwest Logo
10:25 am - 2:55 pm
MDW
-
DAL
4h 30m
1 stop
Southwest Logo
9:45 pm - 11:55 pm
DAL
-
MDW
2h 10mnonstop
$287Southwest
Wed, May 27 - Fri, May 29
Southwest Logo
6:45 am - 9:00 am
MDW
-
DAL
2h 15mnonstop
Southwest Logo
7:50 pm - 10:00 pm
DAL
-
MDW
2h 10mnonstop
$289Southwest
Sat, Jul 4 - Mon, Jul 6
Southwest Logo
6:30 am - 8:50 am
MDW
-
DAL
2h 20mnonstop
Southwest Logo
6:30 pm - 8:40 pm
DAL
-
MDW
2h 10mnonstop
$291Southwest
Wed, Jun 24 - Wed, Jul 1
Southwest Logo
11:55 am - 2:25 pm
ORD
-
DAL
2h 30mnonstop
Southwest Logo
8:05 am - 1:15 pm
DAL
-
ORD
5h 10m
1 stop
$291Southwest
Wed, May 27 - Thu, May 28
Southwest Logo
5:05 am - 7:20 am
MDW
-
DAL
2h 15mnonstop
Southwest Logo
12:00 pm - 5:00 pm
DAL
-
MDW
5h 00m
2 stops
$292Southwest
Wed, Jun 17 - Wed, Jun 17
Southwest Logo
7:45 am - 11:50 am
MDW
-
DAL
4h 05m
1 stop
Southwest Logo
7:50 pm - 10:00 pm
DAL
-
MDW
2h 10mnonstop
$295Southwest
Tue, Jun 9 - Fri, Jun 12
Southwest Logo
10:25 am - 2:55 pm
MDW
-
DAL
4h 30m
1 stop
Southwest Logo
7:45 pm - 11:55 pm
DAL
-
MDW
4h 10m
1 stop
$296Southwest
Wed, May 27 - Fri, May 29
Delta Logo
8:08 am - 3:12 pm
ORD
-
DAL
7h 04m
1 stop
Delta Logo
11:30 am - 8:31 pm
DAL
-
ORD
9h 01m
2 stops
$306Delta
Tue, Jun 23 - Tue, Jun 30
Delta Logo
1:15 pm - 8:30 pm
ORD
-
DAL
7h 15m
1 stop
Delta Logo
12:01 pm - 6:32 pm
DAL
-
ORD
6h 31m
1 stop
$309Delta
Mon, Oct 5 - Wed, Oct 21

Southwest flights from Chicago to Dallas Love Field Airport

Our best Southwest deals on Chicago to Dallas Love Field Airport flight tickets
Southwest
Jun 24
MDW6:30 amChicago Midway
2h 20m
DAL8:50 amDallas Love Field
Jun 27
DAL6:00 amDallas Love Field
2h 15m
MDW8:15 amChicago Midway
$281
Southwest
May 27
MDW10:25 amChicago Midway
4h 30m
1 stop
DAL2:55 pmDallas Love Field
May 29
DAL9:45 pmDallas Love Field
2h 10m
MDW11:55 pmChicago Midway
$287
Southwest
Jul 4
MDW6:05 pmChicago Midway
2h 15m
DAL8:20 pmDallas Love Field
Jul 5
DAL9:25 pmDallas Love Field
2h 10m
MDW11:35 pmChicago Midway
$289

Delta flights from Chicago to Dallas Love Field Airport

Our best Delta deals on Chicago to Dallas Love Field Airport flight tickets
Delta
May 28
MDW5:10 pmChicago Midway
6h 46m
1 stop
DAL11:56 pmDallas Love Field
May 29
DAL7:12 amDallas Love Field
10h 44m
2 stops
MDW5:56 pmChicago Midway
$306
Delta
Oct 5
ORD1:15 pmChicago O'Hare Intl
7h 15m
1 stop
DAL8:30 pmDallas Love Field
Oct 21
DAL12:01 pmDallas Love Field
6h 31m
1 stop
ORD6:32 pmChicago O'Hare Intl
$309
Delta
Jun 12
ORD9:48 amChicago O'Hare Intl
8h 07m
1 stop
DAL5:55 pmDallas Love Field
Jun 15
DAL6:40 pmDallas Love Field
5h 19m
1 stop
ORD11:59 pmChicago O'Hare Intl
$317

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 May 15, 2026.
Use the filters below to find and compare flights from Chicago 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

Wed 6/24

6:30 am-8:50 am

Nonstop2h 20m

Dallas Love Field

Sat 6/27

6:00 am-8:15 am

Nonstop2h 15m

$281

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 5/27

10:25 am-2:55 pm

1 stop4h 30m

Dallas Love Field

Fri 5/29

9:45 pm-11:55 pm

Nonstop2h 10m

$287
Quickest round-trip

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 7/4

6:45 am-9:00 am

Nonstop2h 15m

Dallas Love Field

Mon 7/6

7:50 pm-10:00 pm

Nonstop2h 10m

$289

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 6/24

6:30 am-8:50 am

Nonstop2h 20m

Dallas Love Field

Wed 7/1

6:30 pm-8:40 pm

Nonstop2h 10m

$291

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Wed 5/27

11:55 am-2:25 pm

Nonstop2h 30m

Dallas Love Field

Thu 5/28

8:05 am-1:15 pm

1 stop5h 10m

$291

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 6/17

5:05 am-7:20 am

Nonstop2h 15m

Dallas Love Field

Wed 6/17

12:00 pm-5:00 pm

2 stops5h 00m

$292

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Tue 6/9

7:45 am-11:50 am

1 stop4h 05m

Dallas Love Field

Fri 6/12

7:50 pm-10:00 pm

Nonstop2h 10m

$295

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 5/27

10:25 am-2:55 pm

1 stop4h 30m

Dallas Love Field

Fri 5/29

7:45 pm-11:55 pm

1 stop4h 10m

$296

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Tue 6/23

8:08 am-3:12 pm

1 stop7h 04m

Dallas Love Field

Tue 6/30

11:30 am-8:31 pm

2 stops9h 01m

$306

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Mon 10/5

1:15 pm-8:30 pm

1 stop7h 15m

Dallas Love Field

Wed 10/21

12:01 pm-6:32 pm

1 stop6h 31m

$309

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago 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 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 March, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $46.

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. The lowest ticket price found for a Thursday departure recently was $250. 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 $432.

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 to Dallas Love Field Airport when you can find flight prices for as low as $245. 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 $323 per ticket.

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

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

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

You could potentially save up to 36% on your flight if you consider stops on a Chicago to Dallas Love Field Airport flight.

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

As of May 2026, prices for Chicago to Dallas Love Field Airport flights are approximately 118% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to Dallas Love Field Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago 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 to Dallas Love Field Airport (CHI to DAL) flight deals and tips

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

Best Price Found

$168

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Dallas Love Field Airport from Chicago in the past 72 hours is $168. The best round-trip flight deal from Chicago to Dallas Love Field Airport found on momondo in the last 72 hours is $249.
The fastest flight from Chicago to Dallas Love Field Airport takes 2h 10m
Direct flights go from Chicago to Dallas Love Field Airport every day.
Search flight deals

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

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

    A flight from Chicago to Dallas Love Field will travel around 802.0 mi. A reasonable flight in good conditions will take 2h 10m.

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

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

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

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

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

    The necessary travel and health documents for your Dallas Love Field Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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

Best airlines flying from Chicago to Dallas Love Field Airport

Compare and see reviews for airlines that fly from Chicago to Dallas Love Field Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $68Free CancellationRating
5.6
2,951 reviews
Search Frontier flights
SouthwestPriceFrom $167Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
American AirlinesPriceFrom $177Free CancellationRating
7.1
11,663 reviews
Search American Airlines flights

  • Southwest Flights From Chicago to Dallas Love Field Airport

    Southwest flight deals from Chicago to Dallas Love Field Airport start from $167 round-trip. Over the 50 Southwest flights for this route in a normal week, average airfare is usually $314 round-trip - but some users have found much cheaper deals with momondo.

Why use momondo?

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

Finding the right flight to Dallas from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Dallas quick and easy, saving you time and money.

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

Yes. momondo allows you to filter the results for Chicago to Dallas flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Dallas from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are simply researching potential flights to Dallas, momondo offers a useful price alert feature which will track prices for flights to Dallas from Chicago and alert you when they change.

An easier way to manage your Dallas Love Field Airport trip

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