Oregon Vacations

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Oregon Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel 505 River North

Hotel 505 River North

Downtown Chicago
$608
per person
Dec 24 - Dec 29
found 19 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$781
per person
Dec 24 - Dec 29
found 19 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
$674
per person
Dec 24 - Dec 29
found 19 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
I’m a big guy so the shower was really small but other than that. The hotel was real good. 👍

Reviewed on Oct 11, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
$758
per person
Dec 24 - Dec 29
found 19 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
The staff is super nice and great amenities

Reviewed on Oct 11, 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
$1,151
per person
Dec 24 - Dec 29
found 19 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
$736
per person
Dec 24 - Dec 29
found 19 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I really enjoyed my stay here. I would definitely stay again. The only thing that was missing was cutlery and some wine glasses in the room other than that everything was fantastic.

Reviewed on Oct 11, 2026

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Top Hotel Deals

Sleep Inn & Suites Oregon - Madison

Sleep Inn & Suites Oregon - Madison

1120 Park Street Oregon WI
1.68 km from city center
Book a stay at this business-friendly hotel in Oregon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

1 W Dayton St Madison WI
16.67 km from city center
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
The Edgewater

The Edgewater

1001 Wisconsin Place Madison WI
17.02 km from city center
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

516 Grand Canyon Dr Madison WI
17.04 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4402 E Washington Ave Madison WI
23.21 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

4202 E Towne Blvd Madison WI
22.88 km from city center
Stay at this motel in Madison. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Valued Stay Madison

Valued Stay Madison

6606 Maahic Way Madison WI
16.42 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

8102 Excelsior Dr Madison WI
20.33 km from city center
Book a stay at this family-friendly hotel in Madison. Enjoy free breakfast, free parking, and a free airport shuttle. Our guests praise the breakfast and the ...
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

525 West Johnson Street Madison WI
16.22 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

8102 Watts Rd. Madison WI
18.15 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

5217 E Terrace Dr Madison WI
25.42 km from city center
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
Days Inn & Suites by Wyndham Madison

Days Inn & Suites by Wyndham Madison

4402 E Broadway Srvcs Rd Madison WI
15.1 km from city center
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Dylin

The Dylin

611 E Dayton St Madison WI
17.14 km from city center
Stay at this aparthotel in Madison. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Camp Randall Stadium and Alliant ...
Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

2810 Coho Street Madison WI
12.01 km from city center
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western West Towne Suites

Best Western West Towne Suites

650 Grand Canyon Dr Madison WI
17.04 km from city center
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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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.

Top Flight Deals

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.

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