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Cheap flights from Dallas Love Field Airport to Chicago from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Dallas Love Field Airport to Chicago departing on 12/24. 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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Find the cheapest flights from Dallas Love Field Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:25 am - 12:35 pmDAL-MDW
2h 10mnonstop
Southwest Logo
12:00 pm - 2:30 pmMDW-DAL
2h 30mnonstop
$117Southwest
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Thu, Jan 8 - Sat, Jan 10
Southwest Logo
6:35 am - 8:45 amDAL-MDW
2h 10mnonstop
Southwest Logo
8:20 am - 12:25 pmMDW-DAL
4h 05m1 stop
$123Southwest
Find Deal
Thu, Jan 15 - Sat, Jan 17
Southwest Logo
10:30 am - 12:40 pmDAL-MDW
2h 10mnonstop
Southwest Logo
8:15 am - 1:05 pmMDW-DAL
4h 50m1 stop
$127Southwest
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Wed, Dec 24 - Wed, Dec 31
Southwest Logo
3:35 pm - 7:30 pmDAL-MDW
3h 55m1 stop
Southwest Logo
2:15 pm - 7:10 pmMDW-DAL
4h 55m1 stop
$132Southwest
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Wed, Dec 24 - Wed, Dec 31
Southwest Logo
2:00 pm - 8:00 pmDAL-MDW
6h 00m1 stop
Southwest Logo
9:10 am - 3:15 pmMDW-DAL
6h 05m1 stop
$137Southwest
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Sat, Feb 14 - Sun, Feb 15
Southwest Logo
1:05 pm - 4:35 pmDAL-MDW
3h 30m1 stop
Southwest Logo
8:30 pm - 10:55 pmMDW-DAL
2h 25mnonstop
$158Southwest
Find Deal
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
9:20 am - 1:20 pmDAL-MDW
4h 00m1 stop
Southwest Logo
8:30 pm - 10:55 pmMDW-DAL
2h 25mnonstop
$162Southwest
Find Deal
Fri, Jan 9 - Sun, Jan 11
Southwest Logo
2:10 pm - 7:05 pmDAL-MDW
4h 55m2 stops
Southwest Logo
12:15 pm - 2:45 pmMDW-DAL
2h 30mnonstop
$167Southwest
Find Deal
Thu, Jan 8 - Mon, Jan 12
Southwest Logo
6:50 pm - 9:00 pmDAL-MDW
2h 10mnonstop
Southwest Logo
1:20 pm - 3:45 pmMDW-DAL
2h 25mnonstop
$168Southwest
Find Deal
Tue, Dec 9 - Tue, Dec 16
Southwest Logo
6:00 am - 8:15 amDAL-MDW
2h 15mnonstop
Southwest Logo
7:40 pm - 10:10 pmMDW-DAL
2h 30mnonstop
$171Southwest
Find Deal
Sat, Dec 20 - Sat, Jan 31

Delta flights from Dallas Love Field Airport to Chicago Midway Airport

Our best Delta deals on Dallas Love Field Airport to Chicago Midway Airport flight tickets
Delta
Dec 9
DAL6:37 pmDallas Love Field
5h 10m
1 stop
MDW11:47 pmChicago Midway
Dec 10
MDW5:29 pmChicago Midway
6h 27m
1 stop
DAL11:56 pmDallas Love Field
$177
Find similar
Delta
Dec 8
DAL6:37 pmDallas Love Field
5h 10m
1 stop
MDW11:47 pmChicago Midway
Dec 9
MDW5:29 pmChicago Midway
6h 27m
1 stop
DAL11:56 pmDallas Love Field
$184
Find similar
Delta
Dec 10
DAL6:05 amDallas Love Field
5h 50m
1 stop
MDW11:55 amChicago Midway
Dec 17
MDW5:29 pmChicago Midway
6h 27m
1 stop
DAL11:56 pmDallas Love Field
$188
Find similar

Southwest flights from Dallas Love Field Airport to Chicago Midway Airport

Our best Southwest deals on Dallas Love Field Airport to Chicago Midway Airport flight tickets
Southwest
Jan 8
DAL7:00 amDallas Love Field
2h 10m
MDW9:10 amChicago Midway
Jan 12
MDW12:15 pmChicago Midway
2h 30m
DAL2:45 pmDallas Love Field
$117
Find similar
Southwest
Jan 16
DAL7:45 pmDallas Love Field
2h 10m
MDW9:55 pmChicago Midway
Jan 18
MDW10:00 amChicago Midway
4h 15m
1 stop
DAL2:15 pmDallas Love Field
$123
Find similar
Southwest
Feb 13
DAL6:30 amDallas Love Field
2h 10m
MDW8:40 amChicago Midway
Feb 17
MDW3:10 pmChicago Midway
4h 50m
1 stop
DAL8:00 pmDallas Love Field
$127
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Dallas Love Field Airport to Chicago Midway 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 November 17, 2025.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 1/8

10:25 am-12:35 pm

Nonstop2h 10m

Chicago Midway

Sat 1/10

12:00 pm-2:30 pm

Nonstop2h 30m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 1/15

6:35 am-8:45 am

Nonstop2h 10m

Chicago Midway

Sat 1/17

8:20 am-12:25 pm

1 stop4h 05m

$123

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 12/24

10:30 am-12:40 pm

Nonstop2h 10m

Chicago Midway

Wed 12/31

8:15 am-1:05 pm

1 stop4h 50m

$127

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 12/24

3:35 pm-7:30 pm

1 stop3h 55m

Chicago Midway

Wed 12/31

2:15 pm-7:10 pm

1 stop4h 55m

$132

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 2/14

2:00 pm-8:00 pm

1 stop6h 00m

Chicago Midway

Sun 2/15

9:10 am-3:15 pm

1 stop6h 05m

$137

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 1/8

1:05 pm-4:35 pm

1 stop3h 30m

Chicago Midway

Sun 1/11

8:30 pm-10:55 pm

Nonstop2h 25m

$158

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 1/9

9:20 am-1:20 pm

1 stop4h 00m

Chicago Midway

Sun 1/11

8:30 pm-10:55 pm

Nonstop2h 25m

$162

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 1/8

2:10 pm-7:05 pm

2 stops4h 55m

Chicago Midway

Mon 1/12

12:15 pm-2:45 pm

Nonstop2h 30m

$167

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 12/9

6:50 pm-9:00 pm

Nonstop2h 10m

Chicago Midway

Tue 12/16

1:20 pm-3:45 pm

Nonstop2h 25m

$168

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 12/20

6:00 am-8:15 am

Nonstop2h 15m

Chicago Midway

Sat 1/31

7:40 pm-10:10 pm

Nonstop2h 30m

$171

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 Chicago from

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

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Dallas Love Field Airport, with most prices found around $174. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Dallas Love Field Airport during the month January is also very affordable. Most momondo users find prices during this month for around $228.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Dallas Love Field Airport. The lowest ticket price found for a Saturday departure recently was $152. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Friday is the most expensive day to depart from Dallas Love Field Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $185.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Dallas Love Field Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $196 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $221. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

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

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

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

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

Best Price Found

$178

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Dallas Love Field Airport in the past 72 hours is $178. The best round-trip flight deal from Dallas Love Field Airport to Chicago Midway Airport found on momondo in the last 72 hours is $202.
The fastest flight from Dallas Love Field Airport to Chicago Midway Airport takes 2h 10m
Direct flights go from Dallas Love Field Airport to Chicago Midway Airport every day.
Search flight deals

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

    Chicago Midway is 793.4 mi away from Dallas Love Field. Typically, this will take 2h 10m by plane in normal conditions.

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

    Prices for flights from Dallas Love Field Airport to Chicago Midway Airport are refreshed on a daily basis.

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

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

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

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

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

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

Compare and see reviews for airlines that fly from Dallas Love Field Airport to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $158Free CancellationRating
8.0
4,245 reviews
Search Southwest flights

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

    Across 53 Southwest flights from Dallas Love Field Airport to Chicago Midway Airport this week, the average price was $305, with the best Southwest deals starting from $158 round-trip. 4,245 users have rated Southwest on momondo, with an average score of 8.0/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Hammond
Benton Harbor
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Portage
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Schererville
Valparaiso
Crown Point
Munster
Chesterton
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Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Dallas to Chicago 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 Chicago that suits you.

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

All flight searches from Dallas to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

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

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

Price alerts on flights to Chicago from Dallas are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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