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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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$157
(Southwest)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

July

Average price

$358

Good round-trip deal

$188 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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Highest demand for flights based on searches. 0% potential increase in price ($0 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/10. 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 9/248:20 amDAL - ORD
Nonstop2h 25mSouthwest
Tue 9/307:30 amORD - DAL
Nonstop2h 25mSouthwest
Deal found 6/10$157
This Southwest deal was found by Cheapflights users on 6/10. 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 8/189:15 amMDW - DAL
Nonstop2h 15mSouthwest
Deal found 6/10$157
This Delta deal was found by Cheapflights users on 6/11. 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 7/2612:00 pmDAL - ORD
1 stop5h 08mDelta
Thu 8/145:45 amORD - DAL
1 stop5h 24mDelta
Deal found 6/11$197
This Delta deal was found by Cheapflights users on 6/10. 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 8/123:52 pmDAL - MDW
1 stop5h 57mDelta
Tue 8/1910:11 amMDW - DAL
1 stop7h 32mDelta
Deal found 6/10$197

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 June 12, 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

Wed 9/24

8:20 am-10:45 am

Nonstop2h 25m

Chicago O'Hare Intl

Tue 9/30

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

9:15 am-11:30 am

Nonstop2h 15m

$157

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Wed 8/13

3:52 pm-9:36 pm

1 stop5h 44m

Chicago O'Hare Intl

Tue 8/19

9:45 am-3:07 pm

1 stop5h 22m

$197

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 8/12

3:52 pm-9:49 pm

1 stop5h 57m

Chicago Midway

Tue 8/19

10:11 am-5:43 pm

1 stop7h 32m

$197

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sat 10/11

10:20 am-12:45 pm

Nonstop2h 25m

$79

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Tue 8/5

10:20 am-12:35 pm

Nonstop2h 15m

$79

DallasChicago

DAL - MDW

DALMDW

Dallas Love Field

Sat 12/6

3:45 pm-9:44 pm

1 stop5h 59m

$126

DallasChicago

DAL - ORD

DALORD

Dallas Love Field

Sun 9/7

8:30 am-2:19 pm

1 stop5h 49m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 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 June 8, 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 June 12, 2025.
See what other customers who have flown with 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.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

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 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 $88. On average you can expect to pay $202. 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 Dallas Love Field Airport?

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

Browse thousands of different options on Cheapflights for your next trip

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$158Average$292FlexibilityNo cancel feeOn-time63%

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