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Love Field

$64+ Cheap flights from Chicago (CHI) to Love Field (DAL)

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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DAL
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Dallas Love Field are usually found in September or April, booked 39 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Chicago to Love Field

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Love Field (DAL). 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 15, 2025.

Round-trip from

$137
(Southwest)

One-way from

$64
(Southwest)

Popular in

March

Cheapest in

September

Average price

$186

Good round-trip deal

$180 or less

Good one-way deal

$98 or less
From Chicago (CHI) to Dallas Love Field
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One-way flight from Chicago (CHI) to Dallas Love Field
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Highest demand for flights based on searches. 11% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 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 Chicago (CHI) to Dallas Love Field.
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Price to beat on a one-way flight from Chicago (CHI) to Dallas Love Field.
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Find flight deals from Chicago to Love Field

Cheapest flights from Chicago to Love Field
Explore the most affordable flight options available from Chicago to Love Field. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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 10/227:30 amORD - DAL
Nonstop2h 30mSouthwest
Sat 10/257:35 pmDAL - ORD
Nonstop2h 25mSouthwest
Deal found 9/12$127
This Southwest deal was found by Cheapflights users on 9/12. 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 10/225:30 amMDW - DAL
Nonstop2h 15mSouthwest
Sat 10/253:45 pmDAL - MDW
1 stop4h 35mSouthwest
Deal found 9/12$137
This Southwest deal was found by Cheapflights users on 9/12. 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 10/255:45 amMDW - DAL
Nonstop2h 15mSouthwest
Mon 10/279:55 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 9/12$142
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:30 amMDW - DAL
Nonstop2h 15mSouthwest
Sun 11/25:00 amDAL - MDW
Nonstop2h 15mSouthwest
Deal found 9/13$146
This Southwest deal was found by Cheapflights users on 9/12. 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 10/27:30 amORD - DAL
Nonstop2h 30mSouthwest
Sat 10/410:20 amDAL - ORD
Nonstop2h 25mSouthwest
Deal found 9/12$146
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/224:20 pmORD - DAL
1 stop5h 05mSouthwest
Mon 10/277:05 pmDAL - ORD
Nonstop2h 25mSouthwest
Deal found 9/13$152
This Southwest deal was found by Cheapflights users on 9/15. 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 10/252:15 pmMDW - DAL
Nonstop2h 15mSouthwest
Sat 10/256:05 pmDAL - MDW
Nonstop2h 15mSouthwest
Deal found 9/15$157
This Southwest deal was found by Cheapflights users on 9/15. 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 10/257:30 amORD - DAL
Nonstop2h 30mSouthwest
Sat 10/257:35 pmDAL - ORD
Nonstop2h 25mSouthwest
Deal found 9/15$157
This Southwest deal was found by Cheapflights users on 9/14. 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 10/165:25 amMDW - DAL
Nonstop2h 15mSouthwest
Sat 10/184:40 pmDAL - MDW
1 stop5h 45mSouthwest
Deal found 9/14$167
This Southwest deal was found by Cheapflights users on 9/15. 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 10/157:30 amORD - DAL
Nonstop2h 30mSouthwest
Wed 10/229:05 amDAL - ORD
1 stop7h 20mSouthwest
Deal found 9/15$167
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/315:35 amMDW - DAL
Nonstop2h 15mSouthwest
Wed 11/56:40 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 9/13$168
This Southwest deal was found by Cheapflights users on 9/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:30 pmORD - DAL
Nonstop2h 25mSouthwest
Wed 11/510:35 amDAL - ORD
Nonstop2h 25mSouthwest
Deal found 9/13$168

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Love Field 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 15, 2025.
Use the filters below to find and compare flights from Chicago to Dallas Love Field Airport that are best for you.

Fly from

Chicago

Fly to

Love Field

Route

Depart

Return

Price

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Wed 10/22

5:45 pm-8:10 pm

Nonstop2h 25m

Dallas Love Field

Mon 10/27

7:05 pm-9:30 pm

Nonstop2h 25m

$142

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/22

2:15 pm-7:10 pm

1 stop4h 55m

Dallas Love Field

Sat 10/25

5:55 pm-10:25 pm

1 stop4h 30m

$147

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Wed 10/22

11:25 am-8:40 pm

1 stop9h 15m

Dallas Love Field

Sat 10/25

9:10 am-4:45 pm

2 stops7h 35m

$152

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/29

12:35 pm-6:00 pm

1 stop5h 25m

Dallas Love Field

Sun 11/2

5:00 am-7:15 am

Nonstop2h 15m

$156

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 11/12

8:30 pm-10:55 pm

Nonstop2h 25m

Dallas Love Field

Tue 11/18

9:00 am-11:15 am

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 10/30

12:55 pm-3:10 pm

Nonstop2h 15m

Dallas Love Field

Mon 11/3

6:45 am-8:55 am

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 11/6

5:00 am-7:30 am

Nonstop2h 30m

Dallas Love Field

Mon 11/10

6:00 am-8:15 am

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 10/30

8:25 pm-10:40 pm

Nonstop2h 15m

Dallas Love Field

Sat 11/1

2:15 pm-4:30 pm

Nonstop2h 15m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Tue 10/7

8:25 pm-10:40 pm

Nonstop2h 15m

Dallas Love Field

Wed 10/8

9:55 pm-12:05 am

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 10/15

5:30 am-7:45 am

Nonstop2h 15m

Dallas Love Field

Wed 11/5

5:10 pm-7:25 pm

Nonstop2h 15m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 40 results
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Best time to book a flight from Chicago to Love Field

Have a flexible travel schedule? Discover the best time to fly to Love Field from Chicago 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 Chicago to Dallas Love Field Airport

How far ahead should I book a flight from Chicago to Dallas Love Field Airport?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Love Field. Price data was last updated on September 12, 2025.

The price you pay for your flight from Chicago to Dallas Love Field Airport may vary depending on when you book. For the best chance of a lower fare, look to book 39 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Dallas Love Field Airport (average of $287). Flying from Chicago to Dallas Love Field Airport in March is currently the most expensive (average of $382). 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 CHI to DAL?

Find hourly flight availability from Chicago to Love Field. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Chicago to Dallas Love Field Airport, 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 26% versus a flight in the morning.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Love Field. Price data was last updated on September 14, 2025.

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

Reviews of airlines servicing Love Field

Get insights into the airlines that provide service to Love Field. 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 Love Field. Reviews last updated September 15, 2025.
Get a feel of what it's like to fly with Southwest and Frontier from Chicago to Dallas Love Field Airport 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

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,172 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Boarding

8.1

Entertainment

7.5

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Chicago to Love Field. 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 Chicago to Dallas Love Field Airport?

    Departing from Chicago to Dallas Love Field Airport will take you 2h 25m. Chicago and Dallas Love Field Airport are separated by a distance of 798 mi. Generally, flights for this route are nonstop.

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

    Our cheapest airline available from Chicago to Dallas Love Field Airport is Frontier. Our recent data shows that you can find tickets from as low as $76 on this airline. Additional options worth looking into are Southwest and American Airlines, starting at $157 and $177 round-trip. You may be able to fly from Chicago to Dallas Love Field Airport for 70% less than the average price by searching for these airlines.

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

    Looking for the cheapest flight from Chicago to Dallas Love Field Airport? While on average our users pay $206, our data indicates the cheapest price to be $67. The most popular route (Chicago O'Hare Intl - Dallas Love Field), is priced around $127.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Love Field 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 Chicago to Dallas Love Field Airport?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Dallas Love Field Airport (average of $287). Flying from Chicago to Dallas Love Field Airport in March is currently the most expensive (average of $382). 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

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Alternative routes for Chicago to Love Field

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Love Field

Discover the top 3 airlines that operate flights from Chicago to Love Field. 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 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$188FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$287FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$177Average$287FlexibilityNo cancel feeOn-time71%

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