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Woodstock

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Woodstock Flights as Low as $149

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

Delta
Sat, Aug 22 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 22 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $149 found 1 day ago
JetBlue Airways
Tue, Aug 25 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 1 day ago
American Airlines
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 1 day ago
United
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 1 day ago
Delta
Sat, Aug 22 - Sun, Sep 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 22 from Logan Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $157 found 1 day ago
Delta
Tue, Jul 28 - Mon, Aug 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 28 from Logan Intl. to O'Hare Intl., returning Mon, Aug 10, priced at $161 found 1 day ago
United
Wed, Aug 5 - Tue, Aug 25
BOS
Logan Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 2 days ago
$163
Roundtrip
found 2 days ago
Select United flight, departing Wed, Aug 5 from Logan Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $163 found 2 days ago
Delta
Fri, Aug 21 - Mon, Aug 31
BOS
Logan Intl.
ORD
O'Hare Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Aug 21 from Logan Intl. to O'Hare Intl., returning Mon, Aug 31, priced at $165 found 1 day ago
United
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select United flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $166 found 1 day ago
Bargain Flight
Wed, Oct 21 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$168 Roundtrip, found 2 hours ago
$168
Roundtrip
found 2 hours ago
Select Bargain Flight flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 10, priced at $168 found 2 hours ago
Frontier Airlines
Wed, Oct 21 - Tue, Nov 10
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 2 hours ago
$170
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 10, priced at $170 found 2 hours ago
United
Tue, Aug 11 - Sat, Aug 15
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 11 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Aug 15, priced at $187 found 1 day ago
American Airlines
Fri, Jul 10 - Sun, Jul 12
BOS
Logan Intl.
RFD
Greater Rockford
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jul 10 from Logan Intl. to Greater Rockford, returning Sun, Jul 12, priced at $317 found 2 days ago
American Airlines
Thu, Jul 30 - Sat, Aug 8
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jul 30 from Newark Liberty Intl. Airport to Greater Rockford, returning Sat, Aug 8, priced at $326 found 1 day ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$351 Roundtrip, found 1 day ago
$351
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $351 found 1 day ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$372 Roundtrip, found 1 day ago
$372
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $372 found 1 day ago

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 15 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 $149, 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 $149 right now, why wait?

Woodstock Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$149

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! (1,006 reviews)
"Clean room"

Reviewed on Jul 6, 2026

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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 (321 reviews)
"There is no elevator for 2nd floor stays. Staff is friendly and accommodating. Place is clean. Laundry is the best I have seen mainly because of price. And the equipment works well. Breakfast could be improved but it is fairly typical for places at this price point. Would like to see some chairs ..."

Reviewed on Jul 2, 2026

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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 ...
8.6/10 Excellent! (1,931 reviews)
"Other than the poor experience we had at the Waterfront dining venue and the rooms being a bit dated and on the smaller side, the property was well maintained, had lots of activities available, very nice amenities, and a courteous staff. Overall, I'd give it a 8/10 rating."

Reviewed on Jul 6, 2026

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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! (1,362 reviews)
"Amazing location. Huge room. Everything"

Reviewed on Jul 6, 2026

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Harbor Shores on Lake Geneva
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! (1,496 reviews)
"We love the cove!! We stay there atleast 3-5 times a year! It was amazing as usual and the staff is always super accommodating. We swam this morning after a large storm last night so the only recommendation is to have an outdoor pool cleaning system that can work quickly and better than skimming ..."

Reviewed on Jul 5, 2026

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The Cove Of Lake Geneva
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 ...
9.2/10 Wonderful! (1,010 reviews)
"Everything about this resort is wonderful. Will keep returning!"

Reviewed on Jul 6, 2026

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Lake Lawn Resort
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! (3,306 reviews)
"Room hasn’t been updated in years. Carpets, bathrooms, and kitchen are dingy and old. Loft AC not functioning. The water park is great but rooms are in need of major renovations."

Reviewed on Jul 6, 2026

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Timber Ridge Lodge and Waterpark
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 ...
8.8/10 Excellent! (1,001 reviews)
"We had unusual experience this trip. We were anticipating a fun 4th of July celebration ( actually celebrating on the 3rd. ) While swimming at the pool the weather began to change and a severe storm was heading our way. Staff began warning us. Everyone began to take cover at the closest entrance. ..."

Reviewed on Jul 4, 2026

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Grand Geneva Resort & Spa
See all 1,171 properties in Woodstock
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.