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$79+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
Jul 19 — Jul 261
Sat 7/19
Sat 7/26
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 July 14, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

November

Cheapest in

October

Average price

$257

Good round-trip deal

$187 or less

Good one-way deal

$99 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, 2% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 14, 2025.

This Southwest deal was found by Cheapflights users on 7/14. 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.
Thu 8/218:20 amDAL - ORD
Nonstop2h 25mSouthwest
Sat 8/307:30 amORD - DAL
Nonstop2h 25mSouthwest
Deal found 7/14$157
This Southwest deal was found by Cheapflights users on 7/14. 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.
Thu 8/149:40 pmDAL - MDW
Nonstop2h 10mSouthwest
Mon 8/185:25 amMDW - DAL
Nonstop2h 10mSouthwest
Deal found 7/14$157
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/95:45 amDAL - MDW
1 stop6h 03mDelta
Tue 8/1212:43 pmMDW - DAL
1 stop5h 00mDelta
Deal found 7/13$197
This Delta deal was found by Cheapflights users on 7/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/16:40 pmDAL - ORD
1 stop5h 29mDelta
Tue 8/511:20 amORD - DAL
1 stop6h 35mDelta
Deal found 7/14$253

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 July 14, 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

Thu 8/21

7:05 pm-9:30 pm

Nonstop2h 25m

Chicago O'Hare Intl

Sat 8/30

7:30 am-9:55 am

Nonstop2h 25m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Thu 8/14

9:40 pm-11:50 pm

Nonstop2h 10m

Chicago Midway

Mon 8/18

5:25 am-7:35 am

Nonstop2h 10m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/9

5:45 am-11:48 am

1 stop6h 03m

Chicago Midway

Tue 8/12

12:43 pm-5:43 pm

1 stop5h 00m

$197

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Fri 8/1

4:00 pm-9:30 pm

1 stop5h 30m

Chicago O'Hare Intl

Tue 8/5

11:20 am-5:55 pm

1 stop6h 35m

$248

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Mon 8/11

8:20 am-10:45 am

Nonstop2h 25m

$79

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 8/23

2:25 pm-4:40 pm

Nonstop2h 15m

$79

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sun 8/31

6:28 pm-11:56 pm

1 stop5h 28m

$109

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Fri 9/5

3:52 pm-9:26 pm

1 stop5h 34m

$109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

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 July 14, 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 27% 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 July 13, 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.

Weekly flight availability from Dallas Love Field Airport to Chicago

Explore weekly flight availability from Love Field to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 14, 2025.

The most flights from DAL to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 July 14, 2025.
Get a feel of what it's like to fly with Southwest and Delta 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
4,242 reviews

Boarding

8.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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.
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Entertainment

7.6

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

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.

  • What are the cheapest airlines flying from Dallas Love Field Airport to Chicago round-trip?

    Currently priced at $157, 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. Check Cheapflights for deals on Delta for as low as $197. Users have found that Southwest is 35% 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 $78. On average you can expect to pay $204. The most popular route, (Dallas Love Field - Chicago O'Hare Intl), can usually be booked for $157.

  • 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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Porter
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Chesterton

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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 July 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$301FlexibilityNo cancel feeOn-time63%

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