Deals on vacations and trips to Oregon

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Oregon flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $416, price is now $215 per person
$215
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,175, price is now $526 per person
$526
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,879, price is now $918 per person
$918
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $705, price is now $373 per person
$373
per person
Feb 2 - Feb 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $794, price is now $443 per person
$443
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Oregon hotels deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

2.5 out of 5
1120 Park Street Oregon WI
Free Cancellation
$80 nightly
The price is $91 total per night
$91 total
Nov 30 - Dec 1
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.
Pool
Hot Tub
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $161 total per night
$161 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $135 total per night
$135 total
Nov 25 - Nov 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. Enjoy the hot tub and conveniences like a 24-hour front desk and laundry facilities.
Pool
Hot Tub
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

3 out of 5
5217 E Terrace Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $87 total per night
$87 total
Nov 23 - Nov 24
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like continental breakfast and free self parking. A 24-hour business center, a lobby fireplace, and a communal living room are also on offer.
Pool
Hot Tub
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Free Cancellation
Reserve now, pay when you stay
$45 nightly
The price is $52 total per night
$52 total
Dec 3 - Dec 4
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and laundry facilities are also on offer.
Pet friendly
Parking included
Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

2.5 out of 5
2810 Coho Street Madison WI
Free Cancellation
Reserve now, pay when you stay
$51 nightly
The price is $59 total per night
$59 total
Dec 21 - Dec 22
Total with taxes and fees
This hotel features an indoor pool and a gym. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking. A business center, free WiFi in public areas, and a lobby fireplace are also on offer.
Pool
Breakfast included
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See all available properties in Oregon
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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.

Popular places to visit

Legend at Bergamont

Enjoy a round of golf in Oregon at Legend at Bergamont. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Legend at Bergamont

Frequently asked questions

How much are vacation packages to Oregon?
$215 is all you'll need for a memorable vacation in Oregon. Bundle your hotel and flights into a Travelocity package and watch all the savings start to pile up. With such good prices, traveling has never been so accessible.
How long should my Oregon vacation be?
Most people lock in their hotel for 2 nights in Oregon. But that doesn't necessarily mean you have to. How long you stay really boils down to what you hope to do on your vacation. If your aim is to explore every corner of this impressive place, stay another few nights (or even longer!).
Where can I get the best vacation package deals for Oregon?
You'll discover an excellent range of Oregon package deals on Travelocity. With as many as 400 partner airlines and 1,000,000 properties across the globe, arranging your ideal getaway will be a breeze.
Why should I book my Oregon vacation bundle with Travelocity?
Whether you're searching for the ultimate unplugged getaway or after the fun and excitement of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of websites to find the best deal — our Price Match Guarantee ensures you'll always get the lowest possible price, and our team of customer service experts are available 24/7.
Can I save on my Oregon car rental if I bundle it with a hotel or flight?
You certainly can — bundle your car, hotel and flight into an Oregon vacation package and you'll save a tidy sum. With so much to uncover in and around Oregon, that set of wheels will come in handy. Once you're behind the wheel, crank up the tunes and head to Wrigley Field, a famous attraction about 110 mi from Oregon.
Which airport is best for Oregon?
One of the handiest options is Dane County Regional Airport (MSN), 15 mi north of the hustle and bustle of downtown Oregon. Another choice is Rockford, IL (RFD-Greater Rockford), 50 mi away from central Oregon).
What is there to do in Oregon?
Legend at Bergamont is just one of the awesome sights that make Oregon a popular place to visit. But leave some extra time to experience the city's lesser-known attractions too. This is often where the best vacation memories are made.
Where should I stay when visiting Oregon?
If you're looking for somewhere to base yourself, check out the Sleep Inn & Suites Oregon - Madison. It's the top choice for many visitors.

Photos of local treasures

Browse Oregon vacation photos for more inspiration

Photo by Timothy Kilkenny
Photo by Timothy Kilkenny