Book your flight from Washington, D.C. (DCA) to Chicago (ORD) at the best prices. Fares start from $249.
Washington, D.C.
DCA
→
Chicago
ORD
10/14/2025 – 10/21/2025
Cheap flight deals from Washington, D.C. to Chicago
Average price start from:
i
$159
Round-trip flights from Washington, D.C. to Chicago starting at $159. Book now for the best deals!
One-way from:
i
$89
One-way flights from Washington, D.C. to Chicago starting at $89. Great for flexible travel!
Cheapest day:
i
Monday
Monday is the cheapest day to fly from Washington, D.C. to Chicago. Save more by booking on this day!
Cheapest In:
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$122
Apr 2025
Apr 2025 is the cheapest month to fly from Washington, D.C. to Chicago with prices starting at $122.
Find flight deals from Washington, D.C. to Chicago
Cheapest flights from Washington, D.C. to Chicago
ONEWAY FLIGHTS
LAST MINUTE
CHEAP FLIGHTS
BEST FLIGHTS
Explore the cheapest oneway flights from Washington, D.C. to Chicago spotted daily.
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$89
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$89
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$91
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$91
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$92
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
STL
Unknown City
$96
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$99
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
MDW
Unknown City
$99
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$100
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
STL
Unknown City
$100
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
STL
Unknown City
$109
Non-stop • 60 min
DCA
Washington, D.C.
DCA - Washington, D.C. • 2025-10-14 • 09:00
Unknown
60 min
ORD
Unknown City
$115
Non-stop • 60 min
Price Trends & Analysis
Weekly Price Trends
If your flying dates are flexible, consider flying to Chicago on a Monday.
Monthly Price Trends
Save the most on flights from Washington, D.C. to Chicago in September.
Weather & Climate Information
Temperature
Chicago experiences a humid continental climate, with winter temperatures averaging between 20°F to 30°F and summer temperatures ranging from 70°F to 85°F. The best times for comfortable travel are late spring (May) and early fall (September to October), when temperatures are mild and precipitation is lower.
Rainfall
The best time to visit Chicago is during late spring (May to June) when temperatures are pleasant and outdoor festivals abound. Additionally, the fall (September to October) offers stunning autumn foliage and events like the Chicago Gourmet, providing a vibrant atmosphere with fewer tourists.
Airlines at Chicago
Traveling from Washington, D.C. to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Frontier Airlines, United Airlines, Southwest Airlines, Jetblue Airways provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Washington, D.C. to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Places to Visit in Chicago
Chicago, the Windy City, captivates with its stunning skyline and vibrant neighborhoods, where world-class architecture meets rich cultural diversity. Stroll along the iconic Magnificent Mile, soak in the art at the Art Institute, or savor deep-dish pizza while listening to live blues music. Visitors can immerse themselves in the city's storied history, from the Great Chicago Fire to its thriving arts scene, all while enjoying breathtaking views along the picturesque shores of Lake Michigan. Experience the heartbeat of the Midwest, where every corner offers a new adventure waiting to be discovered.
About Chicago
Discover the beauty of Chicago when flying from Washington, D.C.. 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 Washington, D.C. to Chicago
Traveling from Washington, D.C. to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Frontier Airlines, United Airlines, Southwest Airlines, Jetblue Airways provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Washington, D.C. to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
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 Washington, D.C.. 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, captivates with its stunning skyline and vibrant neighborhoods, where world-class architecture meets rich cultural diversity. Stroll along the iconic Magnificent Mile, soak in the art at the Art Institute, or savor deep-dish pizza while listening to live blues music. Visitors can immerse themselves in the city's storied history, from the Great Chicago Fire to its thriving arts scene, all while enjoying breathtaking views along the picturesque shores of Lake Michigan. Experience the heartbeat of the Midwest, where every corner offers a new adventure waiting to be discovered.
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 Washington, D.C. to Chicago
Traveling from Washington, D.C. to Chicago has never been more convenient, thanks to several reputable airlines offering seamless connectivity between these vibrant cities. Airlines such as Frontier Airlines, United Airlines, Southwest Airlines, Jetblue Airways provide regular flights, ensuring travelers have flexible options to suit their schedules.
Typically, the flight duration is around 10-15 hours, depending on layovers and the chosen route. Most flights from Washington, D.C. to Chicago include one stopover, often in major hubs, allowing for a comfortable transition. For those seeking to explore Chicago, booking with these airlines ensures a smooth travel experience, complete with modern amenities and excellent service.
Frequently Asked Questions
How much does it cost to fly from Washington, D.C. to Chicago?
Flight prices start from $89 for this route. Save more by booking during September and choosing Monday departures.
What's the flight duration from Washington, D.C. to Chicago?
The typical flight time is approximately 10-15 hours, with most routes featuring one stopover for better pricing and convenience.
What airlines serve the Washington, D.C. to Chicago route?
Several airlines operate flights including Frontier Airlines, United Airlines, Southwest Airlines. Compare schedules and prices to find the best option for your travel needs.
When should I book my flight for the best price?
For optimal savings, book 2-3 months ahead and consider traveling during September when demand is lower.
Where can I stay near ORD Airport?
There are several hotels near ORD Airport with convenient shuttle services. Many offer comfortable accommodations for both business and leisure travelers.
What makes Chicago worth visiting?
Chicago combines rich cultural heritage with modern attractions. Visit during pleasant weather months to experience the city at its best.
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