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Woodstock

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Woodstock Flights as Low as $85

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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 September, 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 16 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 $85, 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 $85 right now, why wait?

Woodstock Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$85

Last Minute Hotel Deals in Woodstock

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue, Woodstock, IL
Book a stay at this ski hotel in Woodstock. Enjoy free breakfast, free parking, and a casino. Our guests praise the clean rooms in our reviews. Popular attractions ...
7.8/10 Good! (928 reviews)
"The hotel overall felt safe and clean enough. A couple things I could tell was they re-used the room key card sleeves, and there was a killed spider stuck to the TV guide that nobody had noticed or cleaned up. The TV service they had indicated over 50 channels, only 1 worked. The hotel was smoke ..."

Reviewed on Aug 22, 2025

AmericInn by Wyndham Woodstock IL
Super 8 by Wyndham Woodstock

Super 8 by Wyndham Woodstock

2 out of 5
1220 Davis Rd, Woodstock, IL
Stay at this motel in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions McHenry County Fairgrounds and Bull Valley Golf Club ...
6.2/10 (511 reviews)
"Convenient to our destination. Room was clean and comfortable. Good bed."

Reviewed on Jul 29, 2025

Super 8 by Wyndham Woodstock
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. ...
5.8/10 (248 reviews)
"The sign in process was too long. 3pm check in and only 1 person at the front and there was 4 of us waiting to be checked in."

Reviewed on Aug 18, 2025

Quality Inn & Suites Woodstock near Lake Geneva
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 ...
9/10 Wonderful! (1,230 reviews)
"Food in restaurant was not good. Parking to check in was terrible. Hotel was clean. Staff just okay, not outstanding"

Reviewed on Aug 24, 2025

Harbor Shores on Lake Geneva
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Stay at this 3.5-star beach resort in Fontana. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (1,483 reviews)
"Beautiful area and resort!"

Reviewed on Aug 24, 2025

Abbey Resort and Avani Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Stay at this 3.5-star spa aparthotel in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (2,964 reviews)
"Great water park and convenient dining and fireworks options including shuttle. Thanks!"

Reviewed on Aug 24, 2025

Timber Ridge Lodge and Waterpark
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
Stay at this 4-star business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,006 reviews)
"Clean, convenient and comfortable."

Reviewed on Aug 23, 2025

DoubleTree by Hilton Libertyville - Mundelein
Lodge Geneva National

Lodge Geneva National

4 out of 5
W4240 WI-50, Lake Geneva, WI
Stay at this 4-star 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! (1,264 reviews)
"Also enjoy this property and the entertainment they have"

Reviewed on Aug 23, 2025

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.