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$68+ Cheap flights from Love Field (DAL) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Love Field to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Love Field (DAL) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$127
(Southwest)

One-way from

$68
(Southwest)

Popular in

November

Cheapest in

October

Average price

$187

Good round-trip deal

$171 or less

Good one-way deal

$118 or less
From Dallas Love Field to Chicago (CHI)
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One-way flight from Dallas Love Field to Chicago (CHI)
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Dallas Love Field to Chicago (CHI).
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Price to beat on a one-way flight from Dallas Love Field to Chicago (CHI).
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Find flight deals from Love Field to Chicago

Cheapest flights from Love Field to Chicago
Explore the most affordable flight options available from Love Field to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:20 amDAL - ORD
Nonstop2h 25mSouthwest
Wed 10/11:30 pmORD - DAL
Nonstop2h 20mSouthwest
Deal found 9/11$127
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/18:10 amDAL - MDW
Nonstop2h 15mSouthwest
Wed 10/85:30 amMDW - DAL
Nonstop2h 15mSouthwest
Deal found 9/11$127
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/812:50 pmDAL - ORD
Nonstop2h 30mSouthwest
Wed 10/157:30 amORD - DAL
Nonstop2h 30mSouthwest
Deal found 9/8$128
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:10 amDAL - MDW
Nonstop2h 10mSouthwest
Sat 11/112:55 pmMDW - DAL
1 stop4h 05mSouthwest
Deal found 9/11$133
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:05 pmDAL - ORD
Nonstop2h 25mSouthwest
Sat 10/43:10 pmORD - DAL
1 stop6h 45mSouthwest
Deal found 9/11$137
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:20 pmDAL - MDW
Nonstop2h 10mSouthwest
Sat 10/412:50 pmMDW - DAL
1 stop5h 15mSouthwest
Deal found 9/11$137
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/298:25 amDAL - ORD
Nonstop2h 20mSouthwest
Tue 11/43:45 pmORD - DAL
1 stop6h 25mSouthwest
Deal found 9/9$138
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/117:35 pmDAL - ORD
Nonstop2h 25mSouthwest
Tue 10/145:45 pmORD - DAL
Nonstop2h 25mSouthwest
Deal found 9/10$141
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1110:35 amDAL - ORD
Nonstop2h 25mSouthwest
Wed 11/122:15 pmORD - DAL
Nonstop2h 35mSouthwest
Deal found 9/9$143
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:05 pmDAL - ORD
Nonstop2h 25mSouthwest
Wed 10/295:45 pmORD - DAL
Nonstop2h 25mSouthwest
Deal found 9/11$146
This Southwest deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/129:00 amDAL - MDW
Nonstop2h 15mSouthwest
Sun 11/165:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 9/11$146
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/144:55 pmDAL - ORD
1 stop6h 10mSouthwest
Tue 10/217:30 amORD - DAL
Nonstop2h 30mSouthwest
Deal found 9/10$151

Cheapflights Fare Finder

 
Customize your flight search to find flights from Love Field 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, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from Dallas Love Field Airport to Chicago that are best for you.

Fly from

Love Field

Fly to

Chicago

Route

Depart

Return

Price

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 10/25

9:20 am-2:25 pm

1 stop5h 05m

Chicago O'Hare Intl

Wed 10/29

7:30 am-10:00 am

Nonstop2h 30m

$137

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 10/1

7:20 pm-9:30 pm

Nonstop2h 10m

Chicago Midway

Sat 10/4

12:50 pm-6:05 pm

1 stop5h 15m

$137

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 9/30

5:00 pm-7:15 pm

Nonstop2h 15m

Chicago Midway

Thu 10/2

5:25 am-7:40 am

Nonstop2h 15m

$146

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 12/6

11:40 am-1:55 pm

Nonstop2h 15m

Chicago Midway

Sun 12/7

7:50 am-10:15 am

Nonstop2h 25m

$146

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 11/5

6:50 am-12:15 pm

1 stop5h 25m

Chicago O'Hare Intl

Sat 11/8

2:15 pm-4:50 pm

Nonstop2h 35m

$151

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 12/6

6:10 am-1:30 pm

1 stop7h 20m

Chicago O'Hare Intl

Sat 12/13

2:15 pm-4:50 pm

Nonstop2h 35m

$162

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Tue 10/7

8:25 am-10:45 am

Nonstop2h 20m

Chicago O'Hare Intl

Wed 10/8

5:45 pm-8:10 pm

Nonstop2h 25m

$165

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 10/24

9:55 pm-12:05 am

Nonstop2h 10m

Chicago Midway

Sun 10/26

6:15 am-8:35 am

Nonstop2h 20m

$165

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 11/13

6:00 am-8:15 am

Nonstop2h 15m

Chicago Midway

Sun 11/16

5:00 am-7:30 am

Nonstop2h 30m

$165

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Tue 11/4

6:50 am-12:15 pm

1 stop5h 25m

Chicago O'Hare Intl

Wed 11/5

1:45 pm-10:50 pm

1 stop9h 05m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 45 results
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Best time to book a flight from Love Field to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Love Field with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Dallas Love Field Airport to Chicago

What is the cheapest month to book a flight from Dallas Love Field Airport to Chicago?

Currently, August is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago (average of $245). Flying from Dallas Love Field Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DAL to CHI?

Find hourly flight availability from Love Field to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from Dallas Love Field Airport to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 28% versus a flight at noon.

What is the cheapest day to fly from Dallas Love Field Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Love Field to Chicago. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Dallas Love Field Airport to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Southwest, Spirit Airlines, and Frontier from Dallas Love Field Airport to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Love Field to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Dallas Love Field Airport to Chicago?

    Departing from Dallas Love Field Airport to Chicago will take you 5h 05m. There are 798 mi between Dallas Love Field Airport and Chicago.

  • What is the cheapest airline to fly from Dallas Love Field Airport to Chicago round-trip?

    Currently priced at $158, Southwest will fly you from Dallas Love Field Airport to Chicago and back. In addition to Southwest, many other airlines offer competitively priced options for your trip. Users have found that Southwest is 33% cheaper than the other options available to this destination.

  • What are the cheapest flights from Dallas Love Field Airport to Chicago?

    The cheapest flight price from Dallas Love Field Airport to Chicago is $68. On average you can expect to pay $228. The most popular route, (Dallas Love Field - Chicago O'Hare Intl), can usually be booked for $127.

  • Can I find deals for flights from Love Field to Chicago that include hotel bookings?

    Yes. In addition to deals on Love Field to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Love Field to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Love Field to Chicago.

  • Can I find deals for business class flights from Love Field to Chicago?

    Yes. Cheapflights offers flight deals from Love Field to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Dallas Love Field Airport to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago (average of $245). Flying from Dallas Love Field Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

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Hammond
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Top airline flying from Love Field to Chicago

Discover the top airline that operate flights from Love Field to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$314FlexibilityNo cancel feeOn-time63%

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