Cheap Flights To Woodstock 2025

Photo by Erik Rowley

Woodstock Flights as Low as $90

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Jun 3 - Wed, Jun 4
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, found 19 hours ago
$90
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, Jun 3 from LaGuardia to O'Hare Intl., returning Wed, Jun 4, priced at $90 found 19 hours ago
Spirit Airlines
Tue, Jun 3 - Thu, Jun 5
LGA
LaGuardia
ORD
O'Hare Intl.
$100 Roundtrip, found 19 hours ago
$100
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Tue, Jun 3 from LaGuardia to O'Hare Intl., returning Thu, Jun 5, priced at $100 found 19 hours ago
Frontier Airlines
Sat, May 31 - Sat, Jun 7
DEN
Denver Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 31 from Denver Intl. to O'Hare Intl., returning Sat, Jun 7, priced at $102 found 1 day ago
Delta
Tue, Jul 1 - Tue, Jul 8
LGA
LaGuardia
ORD
O'Hare Intl.
$105 Roundtrip, just found
$105
Roundtrip
just found
Select Delta flight, departing Tue, Jul 1 from LaGuardia to O'Hare Intl., returning Tue, Jul 8, priced at $105 just found
Frontier Airlines
Sat, Jun 7 - Sat, Jun 14
DEN
Denver Intl.
ORD
O'Hare Intl.
$109 Roundtrip, found 5 days ago
$109
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jun 7 from Denver Intl. to O'Hare Intl., returning Sat, Jun 14, priced at $109 found 5 days ago
Spirit Airlines
Sat, Jun 7 - Mon, Jun 9
LGA
LaGuardia
ORD
O'Hare Intl.
$110 Roundtrip, found 19 hours ago
$110
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sat, Jun 7 from LaGuardia to O'Hare Intl., returning Mon, Jun 9, priced at $110 found 19 hours ago
Delta
Fri, Jul 4 - Tue, Jul 8
LGA
LaGuardia
ORD
O'Hare Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Delta flight, departing Fri, Jul 4 from LaGuardia to O'Hare Intl., returning Tue, Jul 8, priced at $115 just found
Frontier Airlines
Sat, May 31 - Thu, Jun 12
DEN
Denver Intl.
ORD
O'Hare Intl.
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 31 from Denver Intl. to O'Hare Intl., returning Thu, Jun 12, priced at $116 found 1 day ago
Frontier Airlines
Sat, May 31 - Fri, Jun 13
DEN
Denver Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 31 from Denver Intl. to O'Hare Intl., returning Fri, Jun 13, priced at $125 found 1 day ago
JetBlue Airways
Mon, Jun 30 - Sat, Jul 5
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$141 Roundtrip, just found
$141
Roundtrip
just found
Select JetBlue Airways flight, departing Mon, Jun 30 from John F. Kennedy Intl. to O'Hare Intl., returning Sat, Jul 5, priced at $141 just found
United
Thu, Jul 17 - Sun, Jul 20
LGA
LaGuardia
ORD
O'Hare Intl.
$145 Roundtrip, just found
$145
Roundtrip
just found
Select United flight, departing Thu, Jul 17 from LaGuardia to O'Hare Intl., returning Sun, Jul 20, priced at $145 just found
American Airlines
Wed, May 28 - Tue, Jun 3
DEN
Denver Intl.
ORD
O'Hare Intl.
$151 Roundtrip, found 2 days ago
$151
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, May 28 from Denver Intl. to O'Hare Intl., returning Tue, Jun 3, priced at $151 found 2 days ago
Delta
Sat, Oct 4 - Tue, Oct 7
BOI
Boise
ORD
O'Hare Intl.
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 4 from Boise to O'Hare Intl., returning Tue, Oct 7, priced at $175 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Thu, Jul 10 - Sun, Jul 13
DEN
Denver Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Jul 10 from Denver Intl. to O'Hare Intl., returning Sun, Jul 13, priced at $325 found 1 day ago
Hawaiian Airlines
Mon, Sep 29 - Sun, Oct 5
BOI
Boise
ORD
O'Hare Intl.
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Mon, Sep 29 from Boise to O'Hare Intl., returning Sun, Oct 5, priced at $326 found 1 day ago
Alaska Airlines
Thu, Oct 2 - Fri, Oct 3
BOI
Boise
ORD
O'Hare Intl.
$360 Roundtrip, found 23 hours ago
$360
Roundtrip
found 23 hours ago
Select Alaska Airlines flight, departing Thu, Oct 2 from Boise to O'Hare Intl., returning Fri, Oct 3, priced at $360 found 23 hours ago

Flights to Woodstock

If you feel like Woodstock is calling your name, then book your next flight to (airport). And with the AARP Travel Center Powered by Expedia®, this trip isn't too far out of reach. With the best rates from Expedia combined with members-only discounts, AARP Travel offers members the best price in travel, guaranteed.

AARP members get exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

Once you have got your trip scheduled, we will show you a full list of deals for your route. Don't forget to look at flights to alternative airports nearby, which can help you score a lower airfare rate.

Airport Transportation

Once you've got your flight scheduled to Woodstock, you may want to book a car so you can get around Woodstock. You can book Woodstock car rentals under our cars tab and hop into the driver's seat as soon as you step outside. For more information, check out the Woodstock Car Rentals Guide.

Things to Do in Woodstock

If you aren't sure where to start, we can help you with that as well. Not to worry—there's lots to do in this city. Woodstock has so much to do, and we can help you get started.

If you're looking for some fun activities to do in Woodstock, make sure you check out our "Things to Do in Woodstock" page for activities and excursions for the whole family.

Book Your Hotel in Woodstock

Woodstock has hotel options in the area, so you'll have little difficulty finding a place to stay close to all the things you want to see. If you need to stay close to the airport, or another attraction in Woodstock, check out our hotel listings page. Remember that you'll get the best price out there when you book with us.

Book Your Woodstock Trip Today

We know that you want to focus less on the logistics and more on the fun stuff, so we provide travel arrangements that fall within your budget. There is no better time than now to start booking that next trip. Book one of our flights today.