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Chicago, IL, USA to Woodstock, VA, USA from $100: 10 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Woodstock, United States of America

How to Get from Chicago to Woodstock: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$100 - PlaneBest price
846 kmDistance
5h 15m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Woodstock with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
Various
Plane
Drive
Average Duration
5h  15m
Estimated price
$166-625
Recommended
Company
Various
Plane
Train
Bus
Average Duration
7h  51m
Estimated price
$100-662
Cheapest
route map
Distance: 846 km
Duration: 5h 15m

See more options

Company
Various
Plane
Subway
Bus
Taxi
Average Duration
6h  50m
Estimated price
$108-432
Company
Various
Plane
Bus
Average Duration
6h 
Estimated price
$190-583
Company
Various
Plane
Subway
Bus
Taxi
Average Duration
7h  12m
Estimated price
$194-1660
Company
Various
Plane
Train
Bus
Average Duration
8h  11m
Estimated price
$1661-1662
Company
Various
Train
Taxi
Average Duration
16h  20m
Estimated price
$1663-1664
Company
Greyhound
Bus
Average Duration
22h  43m
Estimated price
$1665-1666
Company
Various
Train
Taxi
Average Duration
23h  34m
Estimated price
$1667-1668
Company
Various
Drive
Average Duration
11h  31m
Estimated price
$1669-6250
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Traveling From Chicago to Woodstock

The journey from Chicago to Woodstock presents a shift from the bustling city life, filled with skyscrapers and urban energy, to a quaint town that offers a peaceful atmosphere and a charming sense of community.

Best Neighbourhoods in Woodstock

Woodstock features neighborhoods that blend charm, culture, and community spirit.

Downtown Woodstock
• Vibrant arts scene with local galleries
• Variety of restaurants and shops
Cranberry Lake
• Scenic lake views and outdoor activities
• Family-friendly parks and playgrounds
Woodstock Square
• Historic architecture with boutique stores
• Frequent events and community gatherings

Best Times To Visit Woodstock's Attractions

Planning your visit to Woodstock's attractions can enhance your experience dramatically.

Woodstock Opera House
Visit during weekday performances for a more intimate atmosphere.
Marion Park
Early mornings on weekends provide tranquility and stunning sunrise views.
Old McHenry County Courthouse
Midday on weekdays offers a quieter exploration of the historic site.

Woodstock Weather: What to Expect Year-Round

Woodstock experiences a continental climate with four distinct seasons, offering warm summers and cold winters. The best times to visit are during spring and fall, when mild temperatures can enhance your outdoor experiences.

Dining in Woodstock

Try the farm-to-table offerings at the Rustic Roost, where locally sourced ingredients shine in each dish, showcasing the flavors of the Midwest. This cozy eatery provides a relaxed atmosphere that contrasts with Chicago's fast-paced dining scene, allowing you to savor every bite.

Chicago - Woodstock operators

Explore transport companies operating between Chicago and Woodstock, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane
Website
united.com

Plane from Chicago O'Hare to Charlottesville

Average Duration
1h 55m
Estimated price
$6256-1000

Plane from Chicago O'Hare to Washington Dulles

Average Duration
1h 52m
Estimated price
$1001-62550

Plane from Chicago O'Hare to Baltimore

Average Duration
1h 51m
Estimated price
$6251-1000

Plane from Chicago O'Hare to Reagan Washington

Average Duration
1h 52m
Estimated price
$1001-62550

Plane from Chicago O'Hare to Charlottesville via Washington Dulles

Average Duration
4h 7m
Estimated price
$6256-1000

Plane from Chicago O'Hare to Washington Dulles via Pittsburgh

Average Duration
4h 15m
Estimated price
$6253-62550

Plane from Chicago O'Hare to Washington Dulles via Cleveland

Average Duration
4h 22m
Estimated price
$6253-62550
Website
aa.com

Plane from Chicago O'Hare to Charlottesville via New York La Guardia

Average Duration
4h 48m
Estimated price
$6251-6252

Plane from Chicago O'Hare to Reagan Washington

Average Duration
1h 48m
Estimated price
$1001-1002
Website
southwest.com

Plane from Chicago Midway to Reagan Washington

Average Duration
1h 45m
Estimated price
$6256-6257

Plane from Chicago Midway to Baltimore

Average Duration
1h 46m
Estimated price
$6250-6258
Train
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Chicago Union Station to Martinsburg Amtrak Station

Average Duration
15h 21m
Estimated price
$10079-1006

Train from Chicago Union Station to Culpeper Amtrak Station

Average Duration
22h 5m
Estimated price
$1005-100760

Train from BWI Thurgood Marshall to Washington Union Station

Average Duration
33h
Estimated price
$6621-100700
Bus
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Chicago Bus Station to Washington Union Station

Average Duration
19h 10m
Estimated price
$6627-6250
Contact phone
+1-800-827-3490
Website
virginiabreeze.org

Bus from Dulles International Airport to Crooked Run Park and Ride

Average Duration
1h
Estimated price
$66228-10073

Bus from Washington Union Station to Crooked Run Park and Ride

Average Duration
2h 5m
Estimated price
$10072-10077

Chicago to Woodstock: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Woodstock offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on an adventurous road trip from the bustling city of Chicago to the charming town of Woodstock covering a scenic distance of 679 miles. Get ready for a journey filled with diverse landscapes and hidden gems along the way. 💰 The cost of traveling from Chicago to Woodstock by car ranges from $120 to $180, offering budget-friendly options for different travelers. Enjoy the flexibility of a road trip as you plan your stops and explore the attractions en route to your destination.
Average price
$120 - $180
🛫 Begin your trip from Chicago by taking a quick 1 hour and 55-minute direct flight from Chicago O'Hare Airport to Charlottesville Airport. Both United Airlines and American Airlines provide flights for this route. 🚗 Upon arriving at Charlottesville Airport, you can easily rent a car to make the approximately 45-minute drive to Woodstock. Enjoy the scenic journey through the Shenandoah Valley as you head towards your final destination.
Departure Point
Chicago O'Hare Airport
Arrival Point
Charlottesville Airport
🚌 Embark on an exciting journey from Chicago to Woodstock by bus, spanning a travel time of approximately 22 hours and 43 minutes. Sit back, relax, and enjoy the scenic views along the way as you make your way to your destination. 💸 Ticket prices for the bus route between Woodstock and Chicago range between $151 to $256, providing budget-friendly options for travelers seeking an economical mode of transportation. Compare fares and choose the best option that suits your preferences and budget for a hassle-free journey.

Frequently asked questions

Find out more about the route from Chicago to Woodstock.

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The distance between Chicago and Woodstock is approximately 525 miles, or 679 miles by road. If you are traveling from Chicago to Woodstock, it takes around 5 hours and 12 minutes by flying from Chicago O'Hare to Charlottesville and then driving. On the other hand, it takes approximately 11 hours and 31 minutes to drive from Woodstock to Chicago. If you prefer taking a bus, the travel time from Chicago to Woodstock would be about 19 hours and 21 minutes.
The most cost-effective option for traveling from Chicago to Woodstock is to drive. This option costs between $120 to $180 and takes approximately 11 hours and 31 minutes. However, if time efficiency is a priority, the fastest option is to fly from Chicago O'Hare to Charlottesville and then drive. This option takes around 5 hours and 12 minutes and costs between $190 to $480.
The prices for a bus ticket between Woodstock and Chicago can range from $74 to $218. It is important to note that these prices can vary depending on factors such as the time of booking, the bus company, and the class of service. It is recommended to check with different bus operators to find the best price for your travel dates.
To get from Chicago to Woodstock without using public transportation, you can drive. The distance between the two cities is approximately 679 miles, and it takes around 11 hours and 31 minutes to drive. The cost of the trip by car can vary, ranging from $120 to $180 depending on factors such as gas prices and tolls.
To travel from Chicago to Woodstock without a car, you can take a train and then a taxi. The journey typically takes around 16 hours and 20 minutes and costs between $140 and $390. The train route usually includes a transfer in Martinsburg. From there, you can take a taxi to reach your final destination in Woodstock
The flight from Chicago to Woodstock typically takes 1 hour and 52 minutes on the quickest direct flight. This flight is from Chicago O'Hare Airport to Charlottesville Airport. The cost of this flight can vary depending on the airline and the time of booking, but it is typically around $200 to $300 for a one-way ticket.
There are several options for places to stay near Woodstock. There are at least 87 hotels available in the area, offering a range of prices starting at $50. Whether you're looking for a budget-friendly option or a more luxurious stay, there are accommodations to suit your needs. It is recommended to check for availability and make a reservation in advance to ensure a comfortable stay.

Trips from Chicago