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Woodstock

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Woodstock Flights as Low as $123

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

Spirit Airlines
Sun, Aug 3 - Thu, Aug 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$123 Roundtrip, found 3 days ago
$123
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sun, Aug 3 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Aug 7, priced at $123 found 3 days ago
Spirit Airlines
Sun, Aug 3 - Sun, Aug 10
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Aug 3 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, Aug 10, priced at $128 found 2 days ago
Frontier Airlines
Sun, Jul 20 - Mon, Jul 28
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jul 20 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Mon, Jul 28, priced at $133 found 1 day ago
Frontier Airlines
Sun, Aug 10 - Mon, Aug 11
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sun, Aug 10 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Mon, Aug 11, priced at $134 found 3 days ago
American Airlines
Sat, Aug 30 - Mon, Sep 1
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$138 Roundtrip, found 2 days ago
$138
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Aug 30 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Mon, Sep 1, priced at $138 found 2 days ago
Sun Country Airlines
Thu, Jul 24 - Mon, Jul 28
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$139 Roundtrip, just found
$139
Roundtrip
just found
Select Sun Country Airlines flight, departing Thu, Jul 24 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $139 just found
Spirit Airlines
Tue, Jul 22 - Tue, Jul 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$140 Roundtrip, found 18 hours ago
$140
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 29, priced at $140 found 18 hours ago
Spirit Airlines
Wed, Jul 16 - Tue, Jul 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 21 hours ago
$142
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Wed, Jul 16 from Los Angeles Intl. to O'Hare Intl., returning Tue, Jul 22, priced at $142 found 21 hours ago
Frontier Airlines
Sun, Aug 3 - Sun, Aug 10
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Aug 3 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, Aug 10, priced at $144 found 2 days ago
Frontier Airlines
Sun, Jul 20 - Mon, Jul 21
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Jul 20 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Mon, Jul 21, priced at $146 found 1 day ago
Bargain Flight
Wed, Jun 25 - Fri, Jun 27
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Jun 25 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Fri, Jun 27, priced at $159 found 2 days ago
American Airlines
Wed, Jul 23 - Mon, Jul 28
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jul 23 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Mon, Jul 28, priced at $162 found 2 days ago
Delta
Sat, Jul 5 - Sat, Jul 5
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 5 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $179 found 1 day ago
United
Sat, Aug 30 - Mon, Sep 1
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select United flight, departing Sat, Aug 30 from Washington Dulles Intl. to O'Hare Intl., returning Mon, Sep 1, priced at $181 found 3 days ago
Hawaiian Airlines
Tue, Oct 14 - Tue, Oct 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Tue, Oct 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 28, priced at $216 found 1 day ago
Alaska Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 3 hours ago
$216
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $216 found 3 hours 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 $123, 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 $123 right now, why wait?

Woodstock Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$123

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! (881 reviews)
"Staff were great! Stayed for Groundhog festivals"

Reviewed on May 25, 2025

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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 (217 reviews)
"Would visit again"

Reviewed on May 13, 2025

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Quality Inn & Suites Woodstock near Lake Geneva
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 (489 reviews)
Good value
"Comfortable and quiet. Microwave and fridge were provided as requested. Only down was that the carpet needed cleaning."

Reviewed on May 22, 2025

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Super 8 by Wyndham Woodstock
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Stay at this 3-star 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! (1,001 reviews)
"can’t complain"

Reviewed on May 30, 2025

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Hyatt Place Chicago/Hoffman Estates
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! (1,207 reviews)
"a"

Reviewed on Jun 1, 2025

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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
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! (2,837 reviews)
"Rooms are dated and need a refresh, as well as the waterpark itself. Nice staff and fun time"

Reviewed on May 31, 2025

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Timber Ridge Lodge and Waterpark
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! (1,328 reviews)
"the bed are painful to sleep in.very lumpy and pillows are horrible.the bathroom is outdated,not modern at all.we were moved from first room because lights were out and fridge didn't work.whirlpool didn't work downstairs and the food is terrible.we found other places outside the resort."

Reviewed on Jun 1, 2025

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Abbey Resort and Avani Spa
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 ...
9/10 Wonderful! (1,189 reviews)
"The staff is the best.....especially nate at the front desk. You have amazing staff here."

Reviewed on May 31, 2025

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Lodge Geneva National
See all 1,138 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.