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Love Field

$59+ 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 1/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — DAL
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 Thursday and return on a Saturday

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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/28. 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 12/178:30 pmMDW - DAL
Nonstop2h 25mSouthwest
Sat 1/102:30 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 10/28$137
This Southwest deal was found by Cheapflights users on 10/28. 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 12/171:45 pmORD - DAL
1 stop7h 20mSouthwest
Sat 1/1010:35 amDAL - ORD
Nonstop2h 25mSouthwest
Deal found 10/28$147
This Southwest deal was found by Cheapflights users on 10/29. 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 12/48:30 pmMDW - DAL
Nonstop2h 25mSouthwest
Wed 12/106:50 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 10/29$157
This Southwest deal was found by Cheapflights users on 10/29. 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 12/42:15 pmORD - DAL
Nonstop2h 35mSouthwest
Mon 12/810:35 amDAL - ORD
Nonstop2h 25mSouthwest
Deal found 10/29$157
This Southwest deal was found by Cheapflights users on 10/30. 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 12/43:20 pmMDW - DAL
1 stop3h 55mSouthwest
Sat 12/62:25 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 10/30$163
This Southwest deal was found by Cheapflights users on 10/30. 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 12/122:55 pmMDW - DAL
1 stop5h 15mSouthwest
Thu 1/224:50 pmDAL - MDW
Nonstop2h 10mSouthwest
Deal found 10/30$167
This Southwest deal was found by Cheapflights users on 10/29. 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 12/410:05 amMDW - DAL
1 stop4h 25mSouthwest
Mon 12/81:20 pmDAL - MDW
1 stop3h 40mSouthwest
Deal found 10/29$168
This Southwest deal was found by Cheapflights users on 10/29. 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 12/187:55 amMDW - DAL
1 stop5h 25mSouthwest
Thu 12/253:35 pmDAL - MDW
1 stop3h 55mSouthwest
Deal found 10/29$172
This Southwest deal was found by Cheapflights users on 10/29. 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.
Mon 12/157:15 amORD - DAL
2 stops9h 40mSouthwest
Tue 12/1610:35 amDAL - ORD
Nonstop2h 25mSouthwest
Deal found 10/29$172
This Southwest deal was found by Cheapflights users on 10/28. 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 11/278:30 amMDW - DAL
1 stop6h 00mSouthwest
Thu 12/49:05 amDAL - MDW
Nonstop2h 15mSouthwest
Deal found 10/28$176
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 12/175:29 pmMDW - DAL
1 stop6h 27mDelta
Sat 1/105:54 amDAL - MDW
1 stop4h 40mDelta
Deal found 10/28$177
This Southwest deal was found by Cheapflights users on 10/30. 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 12/28:30 pmMDW - DAL
Nonstop2h 25mSouthwest
Fri 12/510:30 amDAL - MDW
Nonstop2h 10mSouthwest
Deal found 10/30$178

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

March

Cheapest in

September

Average price

$253

Good round-trip deal

$187 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Chicago (CHI)-Dallas Love Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Dallas Love Field flights.
Search Deals
From Chicago (CHI) to Dallas Love Field
Search Deals
One-way flight from Chicago (CHI) to Dallas Love Field
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Dallas Love Field.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Dallas Love Field.
Search Deals

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 October 30, 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

MDW - DAL

MDWDAL

Chicago Midway

Sun 1/11

8:30 pm-10:55 pm

Nonstop2h 25m

Dallas Love Field

Thu 1/15

10:40 am-12:50 pm

Nonstop2h 10m

$117

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Wed 12/17

10:50 am-1:15 pm

Nonstop2h 25m

Dallas Love Field

Sun 1/11

6:35 am-8:45 am

Nonstop2h 10m

$137

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Sat 12/13

6:25 am-8:50 am

Nonstop2h 25m

Dallas Love Field

Sat 1/10

2:30 pm-4:40 pm

Nonstop2h 10m

$137

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Sat 1/17

3:05 pm-5:40 pm

Nonstop2h 35m

Dallas Love Field

Mon 1/19

7:10 am-12:15 pm

1 stop5h 05m

$147

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 12/4

8:30 pm-10:55 pm

Nonstop2h 25m

Dallas Love Field

Wed 12/10

6:50 pm-9:00 pm

Nonstop2h 10m

$157

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 12/18

9:25 am-11:50 am

Nonstop2h 25m

Dallas Love Field

Thu 12/25

6:40 pm-8:50 pm

Nonstop2h 10m

$157

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Sat 12/6

2:15 pm-4:50 pm

Nonstop2h 35m

Dallas Love Field

Tue 12/9

10:35 am-1:00 pm

Nonstop2h 25m

$157

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Thu 1/8

2:15 pm-4:55 pm

Nonstop2h 40m

Dallas Love Field

Sun 1/11

6:30 am-2:45 pm

1 stop8h 15m

$162

ChicagoDallas

MDW - DAL

MDWDAL

Chicago Midway

Thu 12/4

1:20 pm-3:45 pm

Nonstop2h 25m

Dallas Love Field

Mon 12/8

1:20 pm-5:00 pm

1 stop3h 40m

$163

ChicagoDallas

ORD - DAL

ORDDAL

Chicago O'Hare Intl

Tue 12/16

2:15 pm-4:50 pm

Nonstop2h 35m

Dallas Love Field

Wed 12/17

6:45 am-12:15 pm

1 stop5h 30m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 40 results
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Compare providers for flights from Chicago to Love Field

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Love Field in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Dallas Love Field Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-Dallas Love Field Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago-Dallas Love Field Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Dallas Love Field Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Dallas Love Field Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 24, 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, April is the cheapest month in which you can book a flight from Chicago to Dallas Love Field Airport (average of $86). Flying from Chicago to Dallas Love Field Airport in January is currently the most expensive (average of $184). 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 October 30, 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 at noon, which can drop the price by up to 22% versus a flight in the evening.

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 October 26, 2025.

Travelers seeking maximum savings on their Chicago to Dallas Love Field Airport flight should consider departing on Thursday 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 October 30, 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

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

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

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

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
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Comfort

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 793 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 71% 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 $305, our data indicates the cheapest price to be $68. The most popular route (Chicago O'Hare Intl - Dallas Love Field), is priced around $117.

  • 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, April is the cheapest month in which you can book a flight from Chicago to Dallas Love Field Airport (average of $86). Flying from Chicago to Dallas Love Field Airport in January is currently the most expensive (average of $184). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$76Average$206FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$157Average$287FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$177Average$287FlexibilityNo cancel feeOn-time71%

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