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Cheap flights from Dallas Love Field Airport to Chicago 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 Dallas Love Field Airport to Chicago departing on 5/28. 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
0 bags

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
9:45 pm - 11:55 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
5:00 am - 7:15 am
MDW
-
DAL
2h 15mnonstop
$245Southwest
Fri, May 29 - Fri, Jun 5
Southwest Logo
9:55 pm - 12:05 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
7:45 am - 11:50 am
MDW
-
DAL
4h 05m
1 stop
$251Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
2:25 pm - 7:25 pm
DAL
-
MDW
5h 00m
1 stop
Southwest Logo
5:15 am - 7:25 am
MDW
-
DAL
2h 10mnonstop
$255Southwest
Sat, Aug 1 - Fri, Aug 7
Southwest Logo
6:10 am - 8:25 am
DAL
-
MDW
2h 15mnonstop
Southwest Logo
7:45 am - 11:50 am
MDW
-
DAL
4h 05m
1 stop
$256Southwest
Sun, Jul 26 - Tue, Jul 28
Southwest Logo
5:35 pm - 10:00 pm
DAL
-
MDW
4h 25m
1 stop
Southwest Logo
7:15 am - 9:25 am
MDW
-
DAL
2h 10mnonstop
$260Southwest
Sat, Aug 22 - Sun, Aug 23
Southwest Logo
6:05 pm - 8:20 pm
DAL
-
MDW
2h 15mnonstop
Southwest Logo
8:45 pm - 11:10 pm
MDW
-
DAL
2h 25mnonstop
$263Southwest
Wed, May 27 - Wed, Jun 3
Delta Logo
10:09 am - 3:40 pm
DAL
-
MDW
5h 31m
1 stop
Delta Logo
12:45 pm - 5:55 pm
MDW
-
DAL
5h 10m
1 stop
$265Delta
Sat, Jun 13 - Wed, Jun 17
Southwest Logo
4:35 pm - 8:10 pm
DAL
-
MDW
3h 35m
1 stop
Southwest Logo
10:05 am - 12:30 pm
MDW
-
DAL
2h 25mnonstop
$269Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
7:15 am - 10:45 am
DAL
-
MDW
3h 30m
1 stop
Southwest Logo
5:00 am - 10:35 am
MDW
-
DAL
5h 35m
1 stop
$270Southwest
Wed, Jun 24 - Fri, Jul 31
Southwest Logo
9:45 pm - 11:55 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
6:55 am - 9:25 am
MDW
-
DAL
2h 30mnonstop
$271Southwest
Fri, May 29 - Sun, May 31

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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
May 24
DAL8:15 pmDallas Love Field
2h 10m
MDW10:25 pmChicago Midway
May 27
MDW11:35 amChicago Midway
2h 25m
DAL2:00 pmDallas Love Field
$281
Southwest
May 24
DAL6:40 amDallas Love Field
2h 10m
MDW8:50 amChicago Midway
May 27
MDW10:25 amChicago Midway
4h 30m
1 stop
DAL2:55 pmDallas Love Field
$287
Southwest
Jul 3
DAL10:50 pmDallas Love Field
2h 10m
MDW1:00 amChicago Midway
Jul 7
MDW8:55 pmChicago Midway
2h 15m
DAL11:10 pmDallas Love Field
$289

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
Jun 13
DAL10:09 amDallas Love Field
5h 31m
1 stop
MDW3:40 pmChicago Midway
Jun 23
MDW6:00 amChicago Midway
5h 32m
1 stop
DAL11:32 amDallas Love Field
$301
Delta
Jun 13
DAL10:09 amDallas Love Field
5h 31m
1 stop
MDW3:40 pmChicago Midway
Jun 14
MDW6:00 amChicago Midway
5h 34m
1 stop
DAL11:34 amDallas Love Field
$311
Delta
Jun 9
DAL6:05 amDallas Love Field
5h 55m
1 stop
MDW12:00 pmChicago Midway
Jun 18
MDW6:00 amChicago Midway
5h 32m
1 stop
DAL11:32 amDallas Love Field
$318

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 May 4, 2026.
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

Cheapest round-trip
Quickest round-trip

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 5/29

9:45 pm-11:55 pm

Nonstop2h 10m

Chicago Midway

Fri 6/5

5:00 am-7:15 am

Nonstop2h 15m

$245

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 7/1

9:55 pm-12:05 am

Nonstop2h 10m

Chicago Midway

Wed 7/8

7:45 am-11:50 am

1 stop4h 05m

$251

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/1

2:25 pm-7:25 pm

1 stop5h 00m

Chicago Midway

Fri 8/7

5:15 am-7:25 am

Nonstop2h 10m

$255

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sun 7/26

6:10 am-8:25 am

Nonstop2h 15m

Chicago Midway

Tue 7/28

7:45 am-11:50 am

1 stop4h 05m

$256

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/22

5:35 pm-10:00 pm

1 stop4h 25m

Chicago Midway

Sun 8/23

7:15 am-9:25 am

Nonstop2h 10m

$260

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 5/27

6:05 pm-8:20 pm

Nonstop2h 15m

Chicago Midway

Wed 6/3

8:45 pm-11:10 pm

Nonstop2h 25m

$263

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 6/13

10:09 am-3:40 pm

1 stop5h 31m

Chicago Midway

Wed 6/17

12:45 pm-5:55 pm

1 stop5h 10m

$265

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 5/27

4:35 pm-8:10 pm

1 stop3h 35m

Chicago Midway

Wed 6/3

10:05 am-12:30 pm

Nonstop2h 25m

$269

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 6/24

7:15 am-10:45 am

1 stop3h 30m

Chicago Midway

Fri 7/31

5:00 am-10:35 am

1 stop5h 35m

$270

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 5/29

9:45 pm-11:55 pm

Nonstop2h 10m

Chicago Midway

Sun 5/31

6:55 am-9:25 am

Nonstop2h 30m

$271

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

What is the cheapest month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Dallas Love Field Airport, with most prices found around $186. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Dallas Love Field Airport during the month November is also very affordable. Most momondo users find prices during this month for around $273.

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

According to our data, Sunday is the cheapest day to fly to Chicago Midway Airport from Dallas Love Field Airport. The lowest ticket price found for a Sunday departure recently was $151. 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 $192 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $226. 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

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

$167

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 $167. The best round-trip flight deal from Dallas Love Field Airport to Chicago Midway Airport found on momondo in the last 72 hours is $324.
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

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

  • 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 $175Free CancellationRating
7.9
4,305 reviews
Search Southwest flights

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

    Across 39 Southwest flights from Dallas Love Field Airport to Chicago Midway Airport this week, the average price was $337, with the best Southwest deals starting from $175 round-trip. 4,307 users have rated Southwest on momondo, with an average score of 7.9/10.

Traveling to a place near Chicago?

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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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