Search Deals on
Oregon Vacation Packages

Build your package with 2 more options

Oregon Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Art Villa

Art Villa

5 out of 5
Save 100% on your flight
Price was $1,900, price is now $958 per person
$958
per person
Dec 24 - Dec 31
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,519, price is now $772 per person
$772
per person
Nov 21 - Nov 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,725, price is now $979 per person
$979
per person
Nov 21 - Nov 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $1,023, price is now $625 per person
$625
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $732, price is now $458 per person
$458
per person
Dec 30 - Jan 3
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $938, price is now $589 per person
$589
per person
Nov 21 - Nov 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Save 100% on your flight
Price was $569, price is now $363 per person
$363
per person
Dec 30 - Jan 3
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy a 24-hour fitness center, parking (surcharge), and onsite spa services. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Oregon Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $306, price is now $179 per person
$179
per person
Jan 7 - Jan 11
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $985, price is now $454 per person
$454
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $694, price is now $364 per person
$364
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,287, price is now $769 per person
$769
per person
Dec 31 - Jan 3
found 2 days ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Oregon Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $931, price is now $472 per person
$472
per person
Dec 24 - Dec 31
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $996, price is now $491 per person
$491
per person
Dec 24 - Dec 31
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $1,226, price is now $606 per person
$606
per person
Nov 25 - Dec 2
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,900, price is now $958 per person
$958
per person
Dec 24 - Dec 31
found 24 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Fri, Nov 14 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$74 Roundtrip, found 2 days ago
$74
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Nov 14 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $74 found 2 days ago
Spirit Airlines
Sat, Nov 15 - Sun, Nov 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Sun, Nov 16, priced at $110 found 1 day ago
United
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select United flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $172 found 1 day ago
All Nippon Airways
Wed, Nov 5 - Mon, Dec 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$999 Roundtrip, found 3 days ago
$999
Roundtrip
found 3 days ago
Select All Nippon Airways flight, departing Wed, Nov 5 from Pudong Intl. to O'Hare Intl., returning Mon, Dec 1, priced at $999 found 3 days ago