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Cheap flights from Dallas Love Field Airport to Chicago from $50

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 1/17. 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
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
Southwest Logo
2:15 pm - 4:55 pmORD-DAL
2h 40mnonstop
$109Southwest
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Wed, Feb 4 - Wed, Feb 11
Southwest Logo
11:20 am - 1:30 pmDAL-MDW
2h 10mnonstop
Southwest Logo
5:20 am - 7:55 amMDW-DAL
2h 35mnonstop
$109Southwest
Find Deal
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
Southwest Logo
2:15 pm - 4:55 pmORD-DAL
2h 40mnonstop
$113Southwest
Find Deal
Tue, Jan 6 - Sun, Jan 11
Southwest Logo
7:00 am - 9:10 amDAL-MDW
2h 10mnonstop
Southwest Logo
7:40 am - 10:15 amMDW-DAL
2h 35mnonstop
$113Southwest
Find Deal
Tue, Jan 6 - Sun, Jan 11
Southwest Logo
12:55 pm - 4:25 pmDAL-MDW
3h 30m1 stop
Southwest Logo
5:20 am - 7:55 amMDW-DAL
2h 35mnonstop
$114Southwest
Find Deal
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
10:35 am - 1:00 pmDAL-ORD
2h 25mnonstop
Southwest Logo
2:15 pm - 4:55 pmORD-DAL
2h 40mnonstop
$117Southwest
Find Deal
Thu, Jan 8 - Sun, Jan 11
Southwest Logo
7:00 am - 9:10 amDAL-MDW
2h 10mnonstop
Southwest Logo
5:20 am - 7:55 amMDW-DAL
2h 35mnonstop
$117Southwest
Find Deal
Sun, Jan 18 - Mon, Jan 19
Southwest Logo
6:35 am - 8:45 amDAL-MDW
2h 10mnonstop
Southwest Logo
10:00 am - 2:15 pmMDW-DAL
4h 15m1 stop
$131Southwest
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Fri, Jan 16 - Sun, Jan 18
Delta Logo
6:00 am - 1:23 pmDAL-ORD
7h 23m1 stop
Delta Logo
2:45 pm - 10:36 pmORD-DAL
7h 51m1 stop
$177Delta
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Sun, Feb 1 - Wed, Feb 11
Delta Logo
2:00 pm - 9:46 pmDAL-MDW
7h 46m1 stop
Delta Logo
5:25 pm - 10:36 pmMDW-DAL
5h 11m1 stop
$177Delta
Find Deal
Tue, Feb 3 - Wed, Feb 11

Southwest flights from Dallas Love Field Airport to Chicago

Our best Southwest deals on Dallas Love Field Airport to Chicago flight tickets
Southwest
Feb 4
DAL10:35 amDallas Love Field
2h 25m
ORD1:00 pmChicago O'Hare Intl
Feb 11
ORD2:15 pmChicago O'Hare Intl
2h 40m
DAL4:55 pmDallas Love Field
$109
Find similar
Southwest
Jan 6
DAL10:35 amDallas Love Field
2h 25m
ORD1:00 pmChicago O'Hare Intl
Jan 11
ORD2:15 pmChicago O'Hare Intl
2h 40m
DAL4:55 pmDallas Love Field
$113
Find similar
Southwest
Jan 17
DAL12:55 pmDallas Love Field
3h 30m
1 stop
MDW4:25 pmChicago Midway
Jan 19
MDW5:20 amChicago Midway
2h 35m
DAL7:55 amDallas Love Field
$114
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
Oct 31
DAL11:40 amDallas Love Field
5h 01m
1 stop
ORD4:41 pmChicago O'Hare Intl
Nov 19
ORD4:26 pmChicago O'Hare Intl
7h 26m
1 stop
DAL11:52 pmDallas Love Field
$177
Find similar
Delta
Oct 31
DAL11:40 amDallas Love Field
5h 01m
1 stop
ORD4:41 pmChicago O'Hare Intl
Nov 18
ORD1:14 pmChicago O'Hare Intl
7h 35m
1 stop
DAL8:49 pmDallas Love Field
$188
Find similar
Delta
Nov 15
DAL11:24 amDallas Love Field
5h 53m
1 stop
ORD5:17 pmChicago O'Hare Intl
Nov 19
ORD9:51 amChicago O'Hare Intl
5h 21m
1 stop
DAL3:12 pmDallas Love Field
$189
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 October 21, 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 2/4

10:35 am-1:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

Wed 2/11

2:15 pm-4:55 pm

Nonstop2h 40m

$109

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 1/17

11:20 am-1:30 pm

Nonstop2h 10m

Chicago Midway

Mon 1/19

5:20 am-7:55 am

Nonstop2h 35m

$109

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Tue 1/6

10:35 am-1:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 1/11

2:15 pm-4:55 pm

Nonstop2h 40m

$113

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 1/6

7:00 am-9:10 am

Nonstop2h 10m

Chicago Midway

Sun 1/11

7:40 am-10:15 am

Nonstop2h 35m

$113

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 1/17

12:55 pm-4:25 pm

1 stop3h 30m

Chicago Midway

Mon 1/19

5:20 am-7:55 am

Nonstop2h 35m

$114

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Thu 1/8

10:35 am-1:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sun 1/11

2:15 pm-4:55 pm

Nonstop2h 40m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sun 1/18

7:00 am-9:10 am

Nonstop2h 10m

Chicago Midway

Mon 1/19

5:20 am-7:55 am

Nonstop2h 35m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 1/16

6:35 am-8:45 am

Nonstop2h 10m

Chicago Midway

Sun 1/18

10:00 am-2:15 pm

1 stop4h 15m

$131

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sun 2/1

6:00 am-1:23 pm

1 stop7h 23m

Chicago O'Hare Intl

Wed 2/11

2:45 pm-10:36 pm

1 stop7h 51m

$177

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 2/3

2:00 pm-9:46 pm

1 stop7h 46m

Chicago Midway

Wed 2/11

5:25 pm-10:36 pm

1 stop5h 11m

$177

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 February is, on average, the cheapest month to fly to Chicago from Dallas Love Field Airport, with most prices found around $177. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Dallas Love Field Airport to Chicago during September average around $188.

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 $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 $937.

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 $222. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $822.

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

$68

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Dallas Love Field Airport in the past 72 hours is $68. The best round-trip flight deal from Dallas Love Field Airport to Chicago found on momondo in the last 72 hours is $174.
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 is 1 airport near Chicago: 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
4,238 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 58 Southwest flights for this route in a normal week, average airfare is usually $324 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
Portage
Lansing
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