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$59+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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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 octubre 30, 2025.

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.
sáb. 12/1310:35 amDAL - ORD
Nonstop2h 25mSouthwest
lun. 2/232:15 pmORD - DAL
Nonstop2h 40mSouthwest
Deal found 10/30$137
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.
jue. 12/187:30 amDAL - ORD
1 stop4h 45mSouthwest
mar. 1/62:15 pmORD - DAL
Nonstop2h 40mSouthwest
Deal found 10/29$147
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.
mié. 12/310:35 amDAL - ORD
Nonstop2h 25mSouthwest
sáb. 12/62:15 pmORD - DAL
Nonstop2h 35mSouthwest
Deal found 10/28$157
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.
jue. 12/112:35 pmDAL - MDW
Nonstop2h 15mSouthwest
mar. 12/165:00 amMDW - DAL
Nonstop2h 30mSouthwest
Deal found 10/28$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.
mar. 12/210:35 amDAL - ORD
Nonstop2h 25mSouthwest
sáb. 12/62:15 pmORD - DAL
Nonstop2h 35mSouthwest
Deal found 10/29$158
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.
mar. 12/29:05 amDAL - MDW
Nonstop2h 15mSouthwest
sáb. 12/66:25 amMDW - DAL
Nonstop2h 25mSouthwest
Deal found 10/29$158
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.
jue. 11/279:55 amDAL - MDW
Nonstop2h 15mSouthwest
jue. 12/410:50 amMDW - DAL
Nonstop2h 25mSouthwest
Deal found 10/28$166
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.
sáb. 12/1310:35 amDAL - ORD
Nonstop2h 25mSouthwest
lun. 12/151:45 pmORD - DAL
1 stop4h 30mSouthwest
Deal found 10/29$167
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.
jue. 11/279:55 amDAL - MDW
Nonstop2h 15mSouthwest
mar. 12/25:35 pmMDW - DAL
Nonstop2h 25mSouthwest
Deal found 10/28$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.
jue. 12/41:20 pmDAL - MDW
1 stop3h 40mSouthwest
lun. 12/83:20 pmMDW - DAL
1 stop3h 55mSouthwest
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.
lun. 12/810:35 amDAL - ORD
Nonstop2h 25mSouthwest
lun. 12/157:15 amORD - DAL
2 stops9h 40mSouthwest
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.
jue. 11/2712:50 pmDAL - MDW
Nonstop2h 15mSouthwest
lun. 12/83:20 pmMDW - DAL
1 stop3h 55mSouthwest
Deal found 10/29$172

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 octubre 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

November

Cheapest in

February

Average price

$197

Good round-trip deal

$177 or less

Good one-way deal

$68 or less
Provider with most accurate pricing for Dallas Love Field-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Dallas Love Field-Chicago (CHI) flights.
Search Deals
From Dallas Love Field to Chicago (CHI)
Search Deals
One-way flight from Dallas Love Field to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 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 Dallas Love Field to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Dallas Love Field to Chicago (CHI).
Search Deals

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 octubre 30, 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

lun. 2/2

10:35 am-1:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

mié. 2/4

2:15 pm-4:55 pm

Nonstop2h 40m

$117

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

vie. 1/9

10:35 am-1:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

lun. 1/12

2:15 pm-4:55 pm

Nonstop2h 40m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

sáb. 1/17

11:20 am-1:30 pm

Nonstop2h 10m

Chicago Midway

lun. 1/19

8:30 pm-10:55 pm

Nonstop2h 25m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

sáb. 1/10

6:25 am-8:35 am

Nonstop2h 10m

Chicago Midway

dom. 1/11

8:30 pm-10:55 pm

Nonstop2h 25m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

sáb. 1/24

11:20 am-1:30 pm

Nonstop2h 10m

Chicago Midway

sáb. 1/24

7:40 pm-10:10 pm

Nonstop2h 30m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

vie. 1/9

2:35 pm-4:45 pm

Nonstop2h 10m

Chicago Midway

dom. 1/11

7:40 am-10:15 am

Nonstop2h 35m

$117

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

sáb. 1/24

2:30 pm-4:40 pm

Nonstop2h 10m

Chicago Midway

lun. 1/26

10:00 am-2:15 pm

1 stop4h 15m

$143

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

dom. 1/18

10:35 am-1:00 pm

Nonstop2h 25m

Chicago O'Hare Intl

lun. 1/19

11:55 am-9:00 pm

1 stop9h 05m

$147

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

jue. 12/4

9:05 am-11:20 am

Nonstop2h 15m

Chicago Midway

lun. 12/8

5:35 pm-8:00 pm

Nonstop2h 25m

$157

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

jue. 12/11

2:35 pm-4:50 pm

Nonstop2h 15m

Chicago Midway

sáb. 12/13

4:30 pm-6:55 pm

Nonstop2h 25m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 41 results
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Compare providers for flights from Love Field to Chicago

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 Love Field to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 Dallas Love Field Airport-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Dallas Love Field Airport-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Dallas Love Field Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Dallas Love Field Airport-Chicago flights, Cheapflights users trust Expedia the most. Expedia 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 Dallas Love Field Airport-Chicago 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 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, November is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago (average of $117). Flying from Dallas Love Field Airport to Chicago in June is currently the most expensive (average of $205). 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 octubre 30, 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 30% 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 October 26, 2025.

Travelers seeking maximum savings on their Dallas Love Field Airport to Chicago flight should consider departing on Saturday evenings 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 octubre 30, 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
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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
8,115 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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

Boarding

8.1

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

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 2h 25m. There are 798 mi between Dallas Love Field Airport and Chicago. Most flights are nonstop.

  • 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 $200. The most popular route, (Dallas Love Field - Chicago O'Hare Intl), can usually be booked for $117.

  • 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, November is the cheapest month in which you can book a flight from Dallas Love Field Airport to Chicago (average of $117). Flying from Dallas Love Field Airport to Chicago in June is currently the most expensive (average of $205). 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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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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$323FlexibilityNo cancel feeOn-time63%

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