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Cheap flights from Dallas Love Field Airport to Chicago 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 Dallas Love Field Airport to Chicago departing on 5/2. 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 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
3:05 pm - 5:30 pm
MDW
-
DAL
2h 25mnonstop
$199Southwest
Thu, Apr 30 - Sat, May 2
Southwest Logo
7:05 pm - 9:15 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
10:20 am - 2:05 pm
MDW
-
DAL
3h 45m
1 stop
$205Southwest
Thu, Apr 30 - Thu, May 7
Southwest Logo
9:45 pm - 11:55 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
5:05 am - 7:20 am
MDW
-
DAL
2h 15mnonstop
$208Southwest
Mon, Jun 1 - Wed, Jun 17
Southwest Logo
7:45 pm - 11:55 pm
DAL
-
MDW
4h 10m
1 stop
Southwest Logo
5:30 am - 7:55 am
MDW
-
DAL
2h 25mnonstop
$209Southwest
Thu, May 14 - Wed, May 20
Southwest Logo
1:30 pm - 4:50 pm
DAL
-
MDW
3h 20m
1 stop
Southwest Logo
10:30 am - 2:25 pm
MDW
-
DAL
3h 55m
1 stop
$210Southwest
Tue, May 5 - Sat, May 9
Southwest Logo
12:45 pm - 5:05 pm
DAL
-
MDW
4h 20m
1 stop
Southwest Logo
10:10 am - 2:50 pm
MDW
-
DAL
4h 40m
1 stop
$214Southwest
Thu, Apr 30 - Thu, May 7
Southwest Logo
4:35 pm - 8:10 pm
DAL
-
MDW
3h 35m
1 stop
Southwest Logo
10:10 am - 3:45 pm
MDW
-
DAL
5h 35m
2 stops
$215Southwest
Tue, Apr 21 - Wed, Apr 22
Southwest Logo
6:15 am - 8:25 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
4:00 pm - 6:25 pm
MDW
-
DAL
2h 25mnonstop
$217Southwest
Tue, May 12 - Tue, May 12
Southwest Logo
9:45 pm - 11:55 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
11:25 am - 4:00 pm
MDW
-
DAL
4h 35m
1 stop
$218Southwest
Mon, Jun 1 - Wed, Jun 17
Southwest Logo
7:20 pm - 11:30 pm
DAL
-
MDW
4h 10m
1 stop
Southwest Logo
6:20 pm - 11:00 pm
MDW
-
DAL
4h 40m
1 stop
$219Southwest
Mon, Jun 1 - Thu, Jun 4

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
Apr 30
DAL9:45 pmDallas Love Field
2h 10m
MDW11:55 pmChicago Midway
May 2
MDW3:05 pmChicago Midway
2h 25m
DAL5:30 pmDallas Love Field
$199
Southwest
Apr 30
DAL7:05 pmDallas Love Field
2h 10m
MDW9:15 pmChicago Midway
May 7
MDW10:20 amChicago Midway
3h 45m
1 stop
DAL2:05 pmDallas Love Field
$205
Southwest
Jun 1
DAL9:45 pmDallas Love Field
2h 10m
MDW11:55 pmChicago Midway
Jun 17
MDW5:05 amChicago Midway
2h 15m
DAL7:20 amDallas Love Field
$208

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
Apr 14
DAL3:53 pmDallas Love Field
6h 35m
1 stop
MDW10:28 pmChicago Midway
Apr 18
MDW5:21 pmChicago Midway
5h 12m
1 stop
DAL10:33 pmDallas Love Field
$347
Delta
Apr 11
DAL10:42 amDallas Love Field
4h 43m
1 stop
MDW3:25 pmChicago Midway
Apr 18
MDW5:21 pmChicago Midway
5h 12m
1 stop
DAL10:33 pmDallas Love Field
$378
Delta
Apr 11
DAL10:42 amDallas Love Field
4h 43m
1 stop
MDW3:25 pmChicago Midway
Apr 14
MDW12:52 pmChicago Midway
4h 58m
1 stop
DAL5:50 pmDallas Love Field
$388

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 April 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

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 4/30

9:45 pm-11:55 pm

Nonstop2h 10m

Chicago Midway

Sat 5/2

3:05 pm-5:30 pm

Nonstop2h 25m

$199

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 4/30

7:05 pm-9:15 pm

Nonstop2h 10m

Chicago Midway

Thu 5/7

10:20 am-2:05 pm

1 stop3h 45m

$205
Quickest round-trip

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 6/1

9:45 pm-11:55 pm

Nonstop2h 10m

Chicago Midway

Wed 6/17

5:05 am-7:20 am

Nonstop2h 15m

$208

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 5/14

7:45 pm-11:55 pm

1 stop4h 10m

Chicago Midway

Wed 5/20

5:30 am-7:55 am

Nonstop2h 25m

$209

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 5/5

1:30 pm-4:50 pm

1 stop3h 20m

Chicago Midway

Sat 5/9

10:30 am-2:25 pm

1 stop3h 55m

$210

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 4/30

12:45 pm-5:05 pm

1 stop4h 20m

Chicago Midway

Thu 5/7

10:10 am-2:50 pm

1 stop4h 40m

$214

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 4/21

4:35 pm-8:10 pm

1 stop3h 35m

Chicago Midway

Wed 4/22

10:10 am-3:45 pm

2 stops5h 35m

$215

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 5/12

6:15 am-8:25 am

Nonstop2h 10m

Chicago Midway

Tue 5/12

4:00 pm-6:25 pm

Nonstop2h 25m

$217

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 6/1

9:45 pm-11:55 pm

Nonstop2h 10m

Chicago Midway

Wed 6/17

11:25 am-4:00 pm

1 stop4h 35m

$218

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 6/1

7:20 pm-11:30 pm

1 stop4h 10m

Chicago Midway

Thu 6/4

6:20 pm-11:00 pm

1 stop4h 40m

$219

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 April is also very affordable. Most momondo users find prices during this month for around $254.

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 $155. 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 $184.

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 $186 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $217. 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

$192

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 $192. The best round-trip flight deal from Dallas Love Field Airport to Chicago Midway Airport found on momondo in the last 72 hours is $275.
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 $166Free CancellationRating
8.0
4,343 reviews
Search Southwest flights

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

    Across 23 Southwest flights from Dallas Love Field Airport to Chicago Midway Airport this week, the average price was $308, with the best Southwest deals starting from $166 round-trip. 4,343 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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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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