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Cheap flights from Dallas Love Field Airport to Chicago from $79

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 10/30. 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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Find the cheapest flights from Dallas Love Field Airport to Chicago

Cheap round-trip flights

Southwest Logo
8:25 am - 10:45 amDAL-ORD
2h 20mnonstop
Southwest Logo
5:45 pm - 8:10 pmORD-DAL
2h 25mnonstop
$157Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
6:25 am - 8:35 amDAL-MDW
2h 10mnonstop
Southwest Logo
5:45 am - 8:00 amMDW-DAL
2h 15mnonstop
$157Southwest
Find Deal
Thu, Oct 23 - Sat, Oct 25
Southwest Logo
6:25 am - 8:35 amDAL-MDW
2h 10mnonstop
Southwest Logo
12:55 pm - 5:00 pmMDW-DAL
4h 05m1 stop
$163Southwest
Find Deal
Thu, Oct 23 - Sat, Oct 25
Southwest Logo
1:10 pm - 10:20 pmDAL-ORD
9h 10m1 stop
Southwest Logo
7:30 am - 10:00 amORD-DAL
2h 30mnonstop
$167Southwest
Find Deal
Thu, Oct 23 - Sat, Oct 25
Southwest Logo
6:25 am - 8:35 amDAL-MDW
2h 10mnonstop
Southwest Logo
6:45 pm - 11:20 pmMDW-DAL
4h 35m1 stop
$167Southwest
Find Deal
Thu, Oct 23 - Mon, Oct 27
Southwest Logo
8:25 am - 10:45 amDAL-ORD
2h 20mnonstop
Southwest Logo
2:15 pm - 4:50 pmORD-DAL
2h 35mnonstop
$168Southwest
Find Deal
Fri, Oct 31 - Mon, Nov 3
Southwest Logo
3:35 pm - 7:30 pmDAL-MDW
3h 55m1 stop
Southwest Logo
3:20 pm - 7:15 pmMDW-DAL
3h 55m1 stop
$168Southwest
Find Deal
Mon, Dec 8 - Tue, Dec 9
Southwest Logo
8:25 am - 10:45 amDAL-ORD
2h 20mnonstop
Southwest Logo
1:50 pm - 10:55 pmORD-DAL
9h 05m2 stops
$172Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Delta Logo
3:59 pm - 11:32 pmDAL-MDW
7h 33m1 stop
Delta Logo
10:49 am - 5:53 pmMDW-DAL
7h 04m1 stop
$209Delta
Find Deal
Fri, Nov 28 - Thu, Dec 4
Delta Logo
6:40 pm - 12:02 amDAL-ORD
5h 22m1 stop
Delta Logo
5:50 pm - 11:58 pmORD-DAL
6h 08m1 stop
$221Delta
Find Deal
Mon, Nov 24 - Mon, Dec 1

Southwest flights from Dallas Love Field Airport to Chicago

Our best Southwest deals on Dallas Love Field Airport to Chicago flight tickets
Southwest
Oct 15
DAL8:25 amDallas Love Field
2h 20m
ORD10:45 amChicago O'Hare Intl
Oct 22
ORD5:45 pmChicago O'Hare Intl
2h 25m
DAL8:10 pmDallas Love Field
$157
Find similar
Southwest
Oct 23
DAL6:25 amDallas Love Field
2h 10m
MDW8:35 amChicago Midway
Oct 25
MDW12:55 pmChicago Midway
4h 05m
1 stop
DAL5:00 pmDallas Love Field
$163
Find similar
Southwest
Oct 23
DAL1:10 pmDallas Love Field
9h 10m
1 stop
ORD10:20 pmChicago O'Hare Intl
Oct 25
ORD7:30 amChicago O'Hare Intl
2h 30m
DAL10:00 amDallas Love Field
$167
Find similar

Delta flights from Dallas Love Field Airport to Chicago

Our best Delta deals on Dallas Love Field Airport to Chicago flight tickets
Delta
Nov 28
DAL3:59 pmDallas Love Field
7h 33m
1 stop
MDW11:32 pmChicago Midway
Dec 4
MDW10:49 amChicago Midway
7h 04m
1 stop
DAL5:53 pmDallas Love Field
$209
Find similar
Delta
Nov 24
DAL6:40 pmDallas Love Field
5h 22m
1 stop
ORD12:02 amChicago O'Hare Intl
Dec 1
ORD5:50 pmChicago O'Hare Intl
6h 08m
1 stop
DAL11:58 pmDallas Love Field
$221
Find similar
Delta
Nov 7
DAL11:40 amDallas Love Field
7h 09m
1 stop
ORD6:49 pmChicago O'Hare Intl
Nov 11
ORD4:21 pmChicago O'Hare Intl
7h 37m
1 stop
DAL11:58 pmDallas Love Field
$238
Find similar

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 September 17, 2025.
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

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 10/15

8:25 am-10:45 am

Nonstop2h 20m

Chicago O'Hare Intl

Wed 10/22

5:45 pm-8:10 pm

Nonstop2h 25m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 10/23

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Sat 10/25

5:45 am-8:00 am

Nonstop2h 15m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 10/23

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Sat 10/25

12:55 pm-5:00 pm

1 stop4h 05m

$163

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Thu 10/23

1:10 pm-10:20 pm

1 stop9h 10m

Chicago O'Hare Intl

Sat 10/25

7:30 am-10:00 am

Nonstop2h 30m

$167

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 10/23

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

Mon 10/27

6:45 pm-11:20 pm

1 stop4h 35m

$167

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Fri 10/31

8:25 am-10:45 am

Nonstop2h 20m

Chicago O'Hare Intl

Mon 11/3

2:15 pm-4:50 pm

Nonstop2h 35m

$168

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Mon 12/8

3:35 pm-7:30 pm

1 stop3h 55m

Chicago Midway

Tue 12/9

3:20 pm-7:15 pm

1 stop3h 55m

$168

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 10/15

8:25 am-10:45 am

Nonstop2h 20m

Chicago O'Hare Intl

Wed 10/22

1:50 pm-10:55 pm

2 stops9h 05m

$172

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 11/28

3:59 pm-11:32 pm

1 stop7h 33m

Chicago Midway

Thu 12/4

10:49 am-5:53 pm

1 stop7h 04m

$209

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Mon 11/24

6:40 pm-12:02 am

1 stop5h 22m

Chicago O'Hare Intl

Mon 12/1

5:50 pm-11:58 pm

1 stop6h 08m

$221

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 cheapest month to fly to Chicago?

The month of October is, on average, the cheapest month to fly to Chicago from Dallas Love Field Airport, with most prices found around $168. If you’re not able to fly to Chicago in October, then February is your next best option. Flight prices from Dallas Love Field Airport to Chicago during February average around $177.

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 Thursday when prices can be found for as low as $282. 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 $911.

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 $223. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $791.

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

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

There is only 1 cabin class available to choose from on Dallas Love Field to Chicago 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

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

$113

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Dallas Love Field Airport in the past 72 hours is $113. The best round-trip flight deal from Dallas Love Field Airport to Chicago found on momondo in the last 72 hours is $199.
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 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • 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 $158Free CancellationRating
8.0
4,242 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 $158 round-trip. Over the 54 Southwest flights for this route in a normal week, average airfare is usually $317 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
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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