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Woodstock

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Woodstock Flights as Low as $58

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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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 March, 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 $58, 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 $58 right now, why wait?

Woodstock Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$58

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! (1,000 reviews)
Great

Reviewed on Jan 3, 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. ...
5.8/10 (290 reviews)
Management was excellent, property inside was well cared for but outside is run down

Reviewed on Nov 5, 2025

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 ...
8.4/10 Very Good! (1,725 reviews)
Nice view of the Lake

Reviewed on Jan 20, 2026

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
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! (3,114 reviews)
Our 3 rooms were spotless! Everyone was very pleasant, and helpful! Our 4 grandkids had a blast, and have allready asked when we can go back!

Reviewed on Jan 20, 2026

Timber Ridge Lodge and Waterpark
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy Hoffman Estates IL
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,016 reviews)
Clean and comfy

Reviewed on Jan 22, 2026

Hyatt Place Chicago/Hoffman Estates
Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
2400 E Geneva St Delavan WI
Book a stay at this beach resort in Delavan. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (1,002 reviews)
The cleanliness of the place was refreshing..

Reviewed on Jan 21, 2026

Lake Lawn Resort
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 ...
8.8/10 Excellent! (1,386 reviews)
My suite was very clean an spacious. I really enjoyed the jacuzzi tub.

Reviewed on Jan 19, 2026

The Cove Of Lake Geneva
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
7036 Grand Geneva Wy Lake Geneva WI
Book a stay at this spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,000 reviews)
Love staying at this hotel for my birthday!! This was our 3rd time staying here!! We also did ski that day at the Mountain top and it was nearby 5mins drive to our room!! The only concern is Room 6307 the shower drainage doesn’t drain well !!

Reviewed on Jan 15, 2026

Grand Geneva Resort & Spa
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.