$74 Cheap Flights from Dallas (DAL) to Chicago (ORD)

View $74 flight on Wed, May 21, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Dallas to Chicago (DAL-ORD)

Prices were available within the past 7 days and start at $74 for one-way flights and $147 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, May 19 - Wed, May 21
DAL
Dallas
ORD
Chicago
$147 Roundtrip, found 2 hours ago
$147
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, May 19 from Dallas to Chicago, returning Wed, May 21, priced at $147 found 2 hours ago
Southwest Airlines
Sat, May 17 - Tue, May 20
DAL
Dallas
ORD
Chicago
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, May 17 from Dallas to Chicago, returning Tue, May 20, priced at $157 just found
Southwest Airlines
Wed, May 21 - Sat, May 24
DAL
Dallas
ORD
Chicago
$163 Roundtrip, just found
$163
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, May 21 from Dallas to Chicago, returning Sat, May 24, priced at $163 just found
Southwest Airlines
Sat, May 17 - Tue, May 20
DAL
Dallas
ORD
Chicago
$167 Roundtrip, just found
$167
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, May 17 from Dallas to Chicago, returning Tue, May 20, priced at $167 just found
Southwest Airlines
Wed, May 21 - Sat, May 31
DAL
Dallas
ORD
Chicago
$172 Roundtrip, just found
$172
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, May 21 from Dallas to Chicago, returning Sat, May 31, priced at $172 just found
Southwest Airlines
Sat, May 17 - Sun, May 25
DAL
Dallas
ORD
Chicago
$173 Roundtrip, found 4 hours ago
$173
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, May 17 from Dallas to Chicago, returning Sun, May 25, priced at $173 found 4 hours ago
Southwest Airlines
Mon, May 19 - Wed, May 21
DAL
Dallas
ORD
Chicago
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, May 19 from Dallas to Chicago, returning Wed, May 21, priced at $177 found 2 hours ago
Southwest Airlines
Fri, Jul 4 - Sat, Jul 5
DAL
Dallas
ORD
Chicago
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Jul 4 from Dallas to Chicago, returning Sat, Jul 5, priced at $179 found 3 hours ago
Southwest Airlines
Sat, May 17 - Tue, May 27
DAL
Dallas
ORD
Chicago
$182 Roundtrip, just found
$182
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, May 17 from Dallas to Chicago, returning Tue, May 27, priced at $182 just found
Delta
Wed, May 21 - Sat, May 31
DAL
Dallas
ORD
Chicago
$207 Roundtrip, just found
$207
Roundtrip
just found
Select Delta flight, departing Wed, May 21 from Dallas to Chicago, returning Sat, May 31, priced at $207 just found

Frequently asked questions

How much does a flight from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD) cost?
You can find cheap return flights from Love Field Airport (DAL) to O’Hare Intl. Airport (ORD) starting from $119. Grab a seat and set off on your next adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Frontier Airlines flight leaving DAL on May 10 2025 and touching down at ORD. The price was last updated on April 22 2025 and has not changed since.
What is the cheapest month to fly from DAL to ORD?
The cheapest flights from DAL to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
You can fly straight from Love Field Airport (DAL) to O’Hare Intl. Airport (ORD) on a Southwest Airlines flight.
What is the cheapest airline that flies from DAL to ORD?
Currently, the cheapest carrier offering one-way flights from DAL to ORD is Southwest Airlines. You can book a seat on this route from $74. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from DAL on May 21 2025. Prices were last updated on April 22 2025 and have not changed since.
How many flights per day from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
Each day, an average of 2 direct flights operate from Love Field Airport (DAL) to O’Hare Intl. Airport (ORD). Select the departure date that fits your schedule best.
What are the most popular departure times for flights from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
The 8 AM departures from DAL to ORD are the top choice for many travelers. These flights can come with a higher price due to their popularity. If you’re looking to save, pick a less crowded time to fly.
What day of the week has the most flights from DAL to ORD?
Depart on a Friday if you’re after the best selection of flights from Love Field Airport (DAL) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
Take the earliest flight at around 7:40AM UTC-6, leaving from Love Field Airport (DAL). You’ll be in the air for approximately 2h 20m, reaching O’Hare Intl. Airport (ORD) at approximately 10:00AM UTC-6.
How long does it take to fly from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
Flights from DAL to ORD have an average travel time of 2 hours and 20 minutes. The total distance between the two is 800 mi.
What airline has the least delays from DAL to ORD?
With 88% of flights usually arriving on schedule, Southwest Airlines has the best on-time performance for direct flights from Love Field Airport (DAL) to O’Hare Intl. Airport (ORD). To monitor your flight status and get notified if anything changes, use the Expedia App.
What is the best time to fly from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
To avoid possible delays on the Love Field Airport (DAL) to O’Hare Intl. Airport (ORD) route, aim to travel before 3 PM. Departures after this hour have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Love Field Airport (DAL)?
Catch a direct flight from Love Field Airport (DAL) to Chicago and land at O’Hare Intl. Airport (ORD). Another entry point into this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from DAL to ORD are typically more expensive. To lock in the best rates, start searching for flights well in advance. That said, if you can play around with your travel dates, it’s possible to score a cheap ticket just before your departure.
Is it cheaper to book a DAL to ORD flight and hotel package?
You can save money by booking a DAL to ORD flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it’s easy to manage it all in one convenient place. After choosing your preferred flights and accommodations, consider adding extras like tours, car rentals and activities.
Can I cancel or change the date of my flight from Love Field Airport (DAL) to O'Hare Intl. Airport (ORD)?
Typically, it’s possible to cancel or reschedule your DAL to ORD flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Check your airline’s policies in your itinerary to see what changes are possible and whether any costs are involved. You’ll also find more details on our Customer Service portal.
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