Search Cheap Flights to
Woodstock

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Woodstock Flights as Low as $68

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

Spirit Airlines
Wed, Oct 23 - Wed, Oct 30
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Wed, Oct 23 from George Bush Intercontinental to O'Hare Intl., returning Wed, Oct 30, priced at $68 found 6 days ago
Spirit Airlines
Sat, Nov 16 - Sat, Nov 16
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$69 Roundtrip, found 4 days ago
$69
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Sat, Nov 16 from George Bush Intercontinental to O'Hare Intl., returning Sat, Nov 16, priced at $69 found 4 days ago
Spirit Airlines
Sat, Nov 9 - Tue, Nov 12
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$74 Roundtrip, found 2 days ago
$74
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Nov 9 from George Bush Intercontinental to O'Hare Intl., returning Tue, Nov 12, priced at $74 found 2 days ago
Spirit Airlines
Wed, Oct 23 - Sat, Oct 26
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 12 hours ago
$75
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Wed, Oct 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Oct 26, priced at $75 found 12 hours ago
Spirit Airlines
Tue, Oct 22 - Tue, Oct 29
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Oct 22 from George Bush Intercontinental to O'Hare Intl., returning Tue, Oct 29, priced at $76 found 1 day ago
Frontier Airlines
Tue, Oct 29 - Wed, Nov 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Nov 6, priced at $78 found 3 days ago
Frontier Airlines
Sat, Oct 19 - Tue, Oct 29
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$79 Roundtrip, found 5 days ago
$79
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 19 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 29, priced at $79 found 5 days ago
Frontier Airlines
Thu, Nov 21 - Tue, Dec 3
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 17 hours ago
$88
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Nov 21 from Charlotte-Douglas Intl. to O'Hare Intl., returning Tue, Dec 3, priced at $88 found 17 hours ago
Spirit Airlines
Tue, Oct 22 - Wed, Oct 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 6 hours ago
$94
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Wed, Oct 23, priced at $94 found 6 hours ago
United
Fri, Oct 25 - Mon, Oct 28
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 1 day ago
$115
Roundtrip
found 1 day ago
Select United flight, departing Fri, Oct 25 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Oct 28, priced at $115 found 1 day ago
American Airlines
Fri, Oct 25 - Mon, Oct 28
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$115 Roundtrip, found 1 day ago
$115
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 25 from Charlotte-Douglas Intl. to O'Hare Intl., returning Mon, Oct 28, priced at $115 found 1 day ago
Delta
Sat, Nov 9 - Sat, Nov 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 9, priced at $171 found 1 day ago
Delta
Tue, Oct 29 - Sat, Nov 2
DAL
Love Field
ORD
O'Hare Intl.
$176 Roundtrip, found 8 hours ago
$176
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Oct 29 from Love Field to O'Hare Intl., returning Sat, Nov 2, priced at $176 found 8 hours ago
Contour Airlines
Mon, Oct 7 - Thu, Oct 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Mon, Oct 7 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Oct 10, priced at $209 found 1 day ago
Alaska Airlines
Wed, Nov 13 - Wed, Nov 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 6 hours ago
$216
Roundtrip
found 6 hours ago
Select Alaska Airlines flight, departing Wed, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 20, priced at $216 found 6 hours ago
JetBlue Airways
Wed, Nov 13 - Wed, Nov 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$362 Roundtrip, found 6 hours ago
$362
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, Nov 13 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 20, priced at $362 found 6 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 October, 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 $68, 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 $68 right now, why wait?

Woodstock Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$67

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
The price is $99 per night from Sep 30 to Oct 1
$99
includes taxes & fees
Sep 30 - Oct 1
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! (803 reviews)
"Nice stay, I had a couple issues on extended stay and the staff responded well! Upgrades seem to be taking place with the new branding, hopefully it will continue to improve. Currently the best branded hotel in Woodstock."

Reviewed on Sep 19, 2024

AmericInn by Wyndham Woodstock IL
Timber Ridge Lodge and Waterpark
Timber Ridge Lodge and Waterpark
3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
The price is $211 per night from Sep 29 to Sep 30
$211
includes taxes & fees
Sep 29 - Sep 30
Stay at this 3.5-star spa aparthotel in Lake Geneva. Enjoy free parking, a full-service spa, and a golf course. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,519 reviews)
"We enjoyed are family time and it wasn’t so pack either"

Reviewed on Sep 25, 2024

Timber Ridge Lodge and Waterpark
Harbor Shores on Lake Geneva
Harbor Shores on Lake Geneva
3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
The price is $156 per night from Oct 27 to Oct 28
$156
includes taxes & fees
Oct 27 - Oct 28
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! (1,210 reviews)
"Love this hotel. Great location. Rooms are clean, modern and comfortable. Staff is friendly."

Reviewed on Sep 22, 2024

Harbor Shores on Lake Geneva
The Ridge Hotel
The Ridge Hotel
4 out of 5
W4240 WI-50, Lake Geneva, WI
The price is $146 per night from Sep 29 to Sep 30
$146
includes taxes & fees
Sep 29 - Sep 30
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! (1,089 reviews)
"Great place to stay, the restaurant doesn’t service breakfast or lunch. There is a cafe with limited food choices. No free coffee in lobby. In room K cups with powdered cream. Property and facilities Needs a refresh."

Reviewed on Sep 25, 2024

The Ridge Hotel
Abbey Resort and Avani Spa
Abbey Resort and Avani Spa
3.5 out of 5
269 Fontana Boulevard, Fontana, WI
The price is $161 per night from Oct 6 to Oct 7
$161
includes taxes & fees
Oct 6 - Oct 7
Stay at this 3.5-star beach resort in Fontana. Enjoy free parking, a full-service spa, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (1,070 reviews)
"Nice room with comfy beds. Clean. Happy with our stay."

Reviewed on Sep 26, 2024

Abbey Resort and Avani Spa
Country Inn & Suites by Radisson, Hoffman Estates, IL
Country Inn & Suites by Radisson, Hoffman Estates, IL
3 out of 5
2280 Barrington Rd, Hoffman Estates, IL
The price is $86 per night from Oct 6 to Oct 7
$86
includes taxes & fees
Oct 6 - Oct 7
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8/10 Very Good! (1,003 reviews)
"Our stay way really nice. Our room was perfect, the complementary breakfast was actually really good."

Reviewed on Sep 23, 2024

Country Inn & Suites by Radisson, Hoffman Estates, IL
Grand Geneva Resort & Spa
Grand Geneva Resort & Spa
4 out of 5
7036 Grand Geneva Wy, Lake Geneva, WI
The price is $302 per night from Sep 29 to Sep 30
$302
includes taxes & fees
Sep 29 - Sep 30
Stay at this 4-star 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 ...
8.4/10 Very Good! (1,001 reviews)
"The place was great , very nice. However the food at the steak house was below average. Maybe just a bad night."

Reviewed on Sep 26, 2024

Grand Geneva Resort & Spa
Holiday Inn Chicago Northwest-Elgin, an IHG Hotel
Holiday Inn Chicago Northwest-Elgin, an IHG Hotel
3 out of 5
495 Airport Rd, Elgin, IL
The price is $129 per night from Oct 13 to Oct 14
$129
includes taxes & fees
Oct 13 - Oct 14
Stay at this 3-star business-friendly hotel in Elgin. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,000 reviews)
"Nice updated lobby. The rooms are in need of a remodel."

Reviewed on Sep 22, 2024

Holiday Inn Chicago Northwest-Elgin, an IHG Hotel
See all 1,164 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.