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$74+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Priceline
3 stars

Round-trip from

$163
(Southwest)

One-way from

$74
(Southwest)

Popular in

June

Cheapest in

February

Average price

$177

Good round-trip deal

$182 or less

Good one-way deal

$108 or less
Provider with most accurate pricing for Dallas Love Field-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Dallas Love Field-Chicago (CHI) flights.
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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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Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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 5/207:10 pmDAL - ORD
Nonstop2h 20mSouthwest
Sat 5/245:45 pmORD - DAL
Nonstop2h 25mSouthwest
Deal found 4/30$163
This Southwest deal was found by Cheapflights users on 4/30. 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 5/207:45 pmDAL - MDW
Nonstop2h 10mSouthwest
Sat 5/245:55 pmMDW - DAL
Nonstop2h 25mSouthwest
Deal found 4/30$163
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/146:39 pmDAL - ORD
1 stop5h 19mDelta
Wed 7/29:49 amORD - DAL
1 stop5h 34mDelta
Deal found 4/30$208
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/33:59 pmDAL - MDW
1 stop5h 28mDelta
Wed 6/116:00 amMDW - DAL
1 stop5h 25mDelta
Deal found 4/29$217

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 May 1, 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

Tue 5/20

7:10 pm-9:30 pm

Nonstop2h 20m

Chicago O'Hare Intl

Sat 5/24

5:45 pm-8:10 pm

Nonstop2h 25m

$163

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 5/20

7:45 pm-9:55 pm

Nonstop2h 10m

Chicago Midway

Sat 5/24

5:55 pm-8:20 pm

Nonstop2h 25m

$163

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 5/21

12:00 pm-5:11 pm

1 stop5h 11m

Chicago O'Hare Intl

Sun 5/25

5:30 am-10:56 am

1 stop5h 26m

$198

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 5/20

3:59 pm-9:27 pm

1 stop5h 28m

Chicago Midway

Sat 5/31

10:25 am-3:09 pm

1 stop4h 44m

$207

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 5/21

8:20 am-10:45 am

Nonstop2h 25m

$74

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 5/20

7:45 pm-9:55 pm

Nonstop2h 10m

$74

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Wed 6/11

5:45 am-11:59 am

1 stop6h 14m

$109

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Fri 5/30

6:30 pm-11:58 pm

1 stop5h 28m

$110

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Tue 5/6

4:00 pm-7:27 am

2 stops15h 27m

$286

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Mon 5/5

6:23 pm-6:01 pm

1 stop23h 38m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 11 results
1
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy2 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 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 Priceline the most. Priceline 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, 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 May 1, 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 31% 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 March 30, 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Dallas to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,406 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Spirit Airlines
6.3
Okay
7,963 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $163, 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 $198. Users have found that Southwest is 35% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Dallas Love Field Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from Dallas Love Field Airport to Chicago are Southwest ($74), Delta ($109), and Spirit Airlines ($286).

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

    The cheapest flight price from Dallas Love Field Airport to Chicago is $73. On average you can expect to pay $199. The most popular route, (Dallas Love Field - Chicago O'Hare Intl), can usually be booked for $163.

  • 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 Dallas Love Field Airport?

Book flights to Dallas Love Field Airport if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Love Field to Chicago

Discover the top 2 airlines 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$134Average$607FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$158Average$293FlexibilityNo cancel feeOn-time63%

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