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Cheap flights from Dallas Love Field Airport to Chicago from $138

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 5/30. 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 Dallas Love Field Airport to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:35 pm - 9:45 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
7:00 pm - 9:15 pm
MDW
-
DAL
2h 15mnonstop
$276Southwest
Sat, May 30 - Sat, Jun 6
Southwest Logo
1:05 pm - 3:30 pm
DAL
-
ORD
2h 25mnonstop
Southwest Logo
2:05 pm - 4:45 pm
ORD
-
DAL
2h 40mnonstop
$281Southwest
Fri, May 29 - Sat, May 30
Southwest Logo
6:30 pm - 8:40 pm
DAL
-
MDW
2h 10mnonstop
Southwest Logo
6:45 am - 9:00 am
MDW
-
DAL
2h 15mnonstop
$281Southwest
Wed, Jul 1 - Sat, Jul 4
Southwest Logo
1:30 pm - 4:55 pm
DAL
-
MDW
3h 25m
1 stop
Southwest Logo
7:00 pm - 9:15 pm
MDW
-
DAL
2h 15mnonstop
$284Southwest
Sat, Jun 6 - Sat, Jun 6
Southwest Logo
4:30 pm - 8:45 pm
DAL
-
MDW
4h 15m
1 stop
Southwest Logo
6:30 am - 8:50 am
MDW
-
DAL
2h 20mnonstop
$287Southwest
Tue, Jul 14 - Sat, Jul 18
Southwest Logo
1:05 pm - 3:30 pm
DAL
-
ORD
2h 25mnonstop
Southwest Logo
1:55 pm - 8:15 pm
ORD
-
DAL
6h 20m
1 stop
$288Southwest
Fri, May 29 - Sat, May 30
Southwest Logo
8:45 am - 11:10 am
DAL
-
ORD
2h 25mnonstop
Southwest Logo
1:35 pm - 9:00 pm
ORD
-
DAL
7h 25m
1 stop
$291Southwest
Wed, May 27 - Wed, May 27
Southwest Logo
9:55 pm - 12:05 am
DAL
-
MDW
2h 10mnonstop
Southwest Logo
8:55 pm - 11:10 pm
MDW
-
DAL
2h 15mnonstop
$291Southwest
Tue, Jun 23 - Tue, Jun 30
Delta Logo
3:01 pm - 8:46 pm
DAL
-
ORD
5h 45m
1 stop
Delta Logo
6:35 am - 2:12 pm
ORD
-
DAL
7h 37m
1 stop
$301Delta
Sat, Jun 27 - Tue, Jun 30
Delta Logo
6:40 pm - 12:04 am
DAL
-
ORD
5h 24m
1 stop
Delta Logo
7:01 am - 5:55 pm
ORD
-
DAL
10h 54m
2 stops
$306Delta
Sat, Jun 27 - Wed, Jul 1

Delta flights from Dallas Love Field Airport to Chicago

Our best Delta deals on Dallas Love Field Airport to Chicago flight tickets
Delta
Jun 27
DAL3:01 pmDallas Love Field
5h 45m
1 stop
ORD8:46 pmChicago O'Hare Intl
Jun 30
ORD6:35 amChicago O'Hare Intl
7h 37m
1 stop
DAL2:12 pmDallas Love Field
$301
Delta
Jun 27
DAL6:40 pmDallas Love Field
5h 24m
1 stop
ORD12:04 amChicago O'Hare Intl
Jul 1
ORD7:01 amChicago O'Hare Intl
10h 54m
2 stops
DAL5:55 pmDallas Love Field
$306
Delta
Sep 8
DAL8:00 amDallas Love Field
8h 36m
2 stops
ORD4:36 pmChicago O'Hare Intl
Sep 19
ORD1:35 pmChicago O'Hare Intl
8h 52m
2 stops
DAL10:27 pmDallas Love Field
$311

Southwest flights from Dallas Love Field Airport to Chicago

Our best Southwest deals on Dallas Love Field Airport to Chicago flight tickets
Southwest
May 30
DAL7:35 pmDallas Love Field
2h 10m
MDW9:45 pmChicago Midway
Jun 6
MDW7:00 pmChicago Midway
2h 15m
DAL9:15 pmDallas Love Field
$276
Southwest
May 29
DAL1:05 pmDallas Love Field
2h 25m
ORD3:30 pmChicago O'Hare Intl
May 30
ORD2:05 pmChicago O'Hare Intl
2h 40m
DAL4:45 pmDallas Love Field
$281
Southwest
Jun 6
DAL1:30 pmDallas Love Field
3h 25m
1 stop
MDW4:55 pmChicago Midway
Jun 6
MDW7:00 pmChicago Midway
2h 15m
DAL9:15 pmDallas Love Field
$284

momondo Fare Finder

 
Customize your flight search to find flights from Dallas Love Field Airport to Chicago 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 17, 2026.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago 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

Sat 5/30

7:35 pm-9:45 pm

Nonstop2h 10m

Chicago Midway

Sat 6/6

7:00 pm-9:15 pm

Nonstop2h 15m

$276

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Fri 5/29

1:05 pm-3:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sat 5/30

2:05 pm-4:45 pm

Nonstop2h 40m

$281

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 7/1

6:30 pm-8:40 pm

Nonstop2h 10m

Chicago Midway

Sat 7/4

6:45 am-9:00 am

Nonstop2h 15m

$281

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 6/6

1:30 pm-4:55 pm

1 stop3h 25m

Chicago Midway

Sat 6/6

7:00 pm-9:15 pm

Nonstop2h 15m

$284

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 7/14

4:30 pm-8:45 pm

1 stop4h 15m

Chicago Midway

Sat 7/18

6:30 am-8:50 am

Nonstop2h 20m

$287

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Fri 5/29

1:05 pm-3:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sat 5/30

1:55 pm-8:15 pm

1 stop6h 20m

$288

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 5/27

8:45 am-11:10 am

Nonstop2h 25m

Chicago O'Hare Intl

Wed 5/27

1:35 pm-9:00 pm

1 stop7h 25m

$291

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 6/23

9:55 pm-12:05 am

Nonstop2h 10m

Chicago Midway

Tue 6/30

8:55 pm-11:10 pm

Nonstop2h 15m

$291

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 6/27

3:01 pm-8:46 pm

1 stop5h 45m

Chicago O'Hare Intl

Tue 6/30

6:35 am-2:12 pm

1 stop7h 37m

$301

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 6/27

6:40 pm-12:04 am

1 stop5h 24m

Chicago O'Hare Intl

Wed 7/1

7:01 am-5:55 pm

2 stops10h 54m

$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 Chicago from

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

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?

What is the cheapest month to fly to Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Dallas Love Field Airport, with most prices found around $103. If you’re not able to fly to Chicago in November, then October is your next best option. Flight prices from Dallas Love Field Airport to Chicago during October average around $124.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $247. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Dallas Love Field Airport to Chicago for around $669.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Dallas Love Field Airport to Chicago during this time can be as low as $228. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $519.

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

Fly from Dallas Love Field to Chicago O'Hare Intl for the best Dallas Love Field - Chicago flight prices

When to book flights from Dallas Love Field Airport to Chicago

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

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

Best Price Found

$99

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Dallas Love Field Airport in the past 72 hours is $99. The best round-trip flight deal from Dallas Love Field Airport to Chicago found on momondo in the last 72 hours is $331.
The fastest flight from Dallas Love Field Airport to Chicago takes 2h 10m
Direct flights go from Dallas Love Field Airport to Chicago every day.
There are 3 airports in Chicago. From Dallas Love Field Airport there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

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

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

    There are 802.0 mi between Dallas Love Field and Chicago. 2h 10m is a normal flight duration for this route.

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

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

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Dallas Love Field Airport to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 Dallas Love Field Airport to Chicago?

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

Best airlines flying from Dallas Love Field Airport to Chicago

Compare and see reviews for airlines that fly from Dallas Love Field Airport to Chicago with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $175Free CancellationRating
8.0
4,291 reviews
Search Southwest flights

  • Southwest Flights From Dallas Love Field Airport to Chicago

    Southwest flight deals from Dallas Love Field Airport to Chicago start from $175 round-trip. Over the 47 Southwest flights for this route in a normal week, average airfare is usually $343 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

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

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Dallas to Chicago. momondo saves you time and could save you money on your trip.

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

Flights from Dallas to Chicago 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 Dallas to Chicago?

Once all potential Dallas to Chicago 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 Dallas to Chicago right now. Can momondo alert me if prices change?

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

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport