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Woodstock

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Woodstock Flights as Low as $152

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Cheap Flights to Woodstock

Fall in love at first flight with your vacation to Woodstock by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Woodstock on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Woodstock, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Woodstock

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Woodstock with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Woodstock?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Woodstock are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Woodstock?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Woodstock.

What airport is best to fly into Woodstock?

When you’re planning your trip to Woodstock, convenience is the name of the game. Luckily, Woodstock Dupage Airport is nearby so you can deplane and get going on checking off everything on your Woodstock must-do list.

How much are flights to Woodstock?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Woodstock on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $152, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Woodstock?

The trick to saving a stack of cash on your flight to Woodstock? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $152 right now, why wait?

Woodstock Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$157

Last Minute Hotel Deals in Woodstock

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

3 out of 5
990 Lake Avenue Woodstock IL
Book a stay at this ski hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions ...
8/10 Very Good! (1,001 reviews)
"The property had everything that I needed. It is located conveniently to the local restaurants, Chicago Metra train station, and was close to the Illinois Railroad Museum, which was my primary reason for going here. The room was clean, quiet, and sufficiently setup with the basics like towels and ..."

Reviewed on Jun 5, 2026

AmericInn by Wyndham Woodstock IL
Quality Inn & Suites Woodstock near Lake Geneva

Quality Inn & Suites Woodstock near Lake Geneva

2.5 out of 5
1785 S Eastwood Dr Woodstock IL
Book a stay at this business-friendly hotel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
6/10 (314 reviews)
"There's not a ton of quality at this Quality Inn. The beds were comfortable, the bedspreads, stained. The curtains in our room, stained. The outer doors either didn't lock or close well, but there didn't seem to be much security in them. We didn't use the pool. Breakfast was basic, but fine. Basically, ..."

Reviewed on Jun 4, 2026

Quality Inn & Suites Woodstock near Lake Geneva
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
Book a stay at this beach resort in Fontana. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in ...
Abbey Resort and Avani Spa
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in ...
9.2/10 Wonderful! (1,357 reviews)
"The property was awesome. The staff was awesome the manager great people great place to stay."

Reviewed on Jun 5, 2026

Harbor Shores on Lake Geneva
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (3,279 reviews)
"We had an amazing time"

Reviewed on Jun 5, 2026

Timber Ridge Lodge and Waterpark
The Cove Of Lake Geneva

The Cove Of Lake Geneva

3.5 out of 5
111 Center St Lake Geneva WI
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, 2 hot tubs, and room service. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,484 reviews)
"It was ok"

Reviewed on Jun 4, 2026

The Cove Of Lake Geneva
Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
7036 Grand Geneva Way Lake Geneva WI
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (1,000 reviews)
"Very nice property"

Reviewed on May 31, 2026

Holiday Inn Club Vacations at Lake Geneva Resort by IHG
Lodge Geneva National

Lodge Geneva National

4 out of 5
W4240 WI-50 Lake Geneva WI
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,376 reviews)
"Hotel was okay went for a birthday trip. Staff were nice. Had dirty sheets on bed and didn’t notice until almost time to check out. Not sure why considered 4 star hotel— more like 3 star. Did not live up to expectations. Breakfast from on site coffee spot was not edible. If I go back to Lake Geneva ..."

Reviewed on Jun 4, 2026

Lodge Geneva National
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.