Book your flight from Grapevine (DFW) to Chicago (ORD) at the best prices. Fares start from $389.
Grapevine
DFW
→
Chicago
ORD
10/14/2025 – 10/21/2025
Cheap flight deals from Grapevine to Chicago
Average price start from:
i
$92
Round-trip flights from Grapevine to Chicago starting at $92. Book now for the best deals!
One-way from:
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$53
One-way flights from Grapevine to Chicago starting at $53. Great for flexible travel!
Cheapest day:
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Tuesday
Tuesday is the cheapest day to fly from Grapevine to Chicago. Save more by booking on this day!
Cheapest In:
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$28
Jul 2025
Jul 2025 is the cheapest month to fly from Grapevine to Chicago with prices starting at $28.
Find flight deals from Grapevine to Chicago
Cheapest flights from Grapevine to Chicago
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
BEST FLIGHTS
Explore the cheapest oneway flights from Grapevine to Chicago spotted daily.
DFW
Grapevine
DFW - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$53
Non-stop • 60 min
IAH
Grapevine
IAH - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$54
Non-stop • 60 min
HOU
Grapevine
HOU - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$55
Non-stop • 60 min
IAH
Grapevine
IAH - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$55
Non-stop • 60 min
DFW
Grapevine
DFW - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$55
Non-stop • 60 min
DFW
Grapevine
DFW - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$57
Non-stop • 60 min
DFW
Grapevine
DFW - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
CVG
Unknown City
$59
Non-stop • 60 min
HOU
Grapevine
HOU - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$62
Non-stop • 60 min
AUS
Grapevine
AUS - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$65
Non-stop • 60 min
HOU
Grapevine
HOU - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$70
Non-stop • 60 min
AUS
Grapevine
AUS - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$71
Non-stop • 60 min
AUS
Grapevine
AUS - Grapevine • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$78
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
Save money by choosing Tuesday flights to Chicago.
Monthly Price Trends
Best time to book flights from Grapevine to Chicago is during April.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate with cold winters, where temperatures can drop to 20°F (-6°C), and hot summers, reaching highs around 85°F (29°C). The best times for comfortable travel are spring (April to June) and early fall (September to October), when temperatures are mild and pleasant.
Rainfall
The best time to visit Chicago is during late spring (May to early June) when the weather is mild and blooming flowers enhance the city's beauty. Additionally, this period coincides with popular events like the Chicago Blues Festival and the Chicago Gourmet, allowing you to experience the vibrant local culture without the summer crowds.
Airlines at Chicago
Discover excellent flight options from Grapevine to Chicago with top airlines including Frontier Airlines, Spirit Airlines, Southwest Airlines, American Airlines. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Grapevine to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline and vibrant neighborhoods, each offering a unique flavor of culture and history. Visitors can explore the iconic Art Institute, marvel at Millennium Park's "Cloud Gate," and savor deep-dish pizza that’s become a culinary legend. As you stroll along the picturesque Lake Michigan shoreline, you’ll encounter a rich tapestry of music, art, and architecture that invites you to experience the heartbeat of this dynamic metropolis, making every moment in Chicago unforgettable.
About Chicago
Discover the beauty of Chicago when flying from Grapevine. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.
Airlines Flying from Grapevine to Chicago
Discover excellent flight options from Grapevine to Chicago with top airlines including Frontier Airlines, Spirit Airlines, Southwest Airlines, American Airlines. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Grapevine to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Hotels in Chicago
When staying in Chicago, look for hotels with easy access to ORD Airport. Most properties provide shuttle services for seamless airport transfers.
About Chicago
Discover the beauty of Chicago when flying from Grapevine. This captivating city combines rich heritage with contemporary charm, offering something special for every traveler. Plan your visit during off-peak periods for optimal savings and a more relaxed experience.
Places to Visit in Chicago
Chicago, the Windy City, dazzles with its stunning skyline and vibrant neighborhoods, each offering a unique flavor of culture and history. Visitors can explore the iconic Art Institute, marvel at Millennium Park's "Cloud Gate," and savor deep-dish pizza that’s become a culinary legend. As you stroll along the picturesque Lake Michigan shoreline, you’ll encounter a rich tapestry of music, art, and architecture that invites you to experience the heartbeat of this dynamic metropolis, making every moment in Chicago unforgettable.
Hotels in Chicago
When staying in Chicago, look for hotels with easy access to ORD Airport. Most properties provide shuttle services for seamless airport transfers.
Airlines Flying from Grapevine to Chicago
Discover excellent flight options from Grapevine to Chicago with top airlines including Frontier Airlines, Spirit Airlines, Southwest Airlines, American Airlines. These carriers offer reliable service and comfortable connections between these popular destinations.
The average flight time is approximately 10-15 hours, with most routes featuring one stopover for optimal pricing and convenience. When planning your journey from Grapevine to Chicago, these airlines provide excellent connectivity and modern aircraft for a pleasant travel experience.
Frequently Asked Questions
What is the cheapest flight from Grapevine to Chicago?
The cheapest fare is $53. For the best deals, consider booking during April and flying on Tuesday.
How long is the flight from Grapevine to Chicago?
Average flight time is around 10-15 hours, depending on layovers and the chosen route. Most flights include one stopover for optimal pricing.
Which airlines fly from Grapevine to Chicago?
Multiple airlines operate this route including Frontier Airlines, Spirit Airlines, Southwest Airlines. Check current schedules and availability for the best options.
What is the best time to book flights?
Booking 2–3 months in advance usually gives the best prices. Consider flying during April for additional savings.
Are there hotels near ORD Airport?
Yes, several hotels are conveniently located near ORD Airport, including options with shuttle services for easy airport access.
What should I know about Chicago?
Chicago offers a perfect blend of culture, history, and modern attractions. The best time to visit is during pleasant weather months for optimal experiences.
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