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Oregon Vacation Packages

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Oregon Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Ohio House Motel

Ohio House Motel

3 out of 5
Save 100% on your flight
Price was $473, price is now $326 per person
$326
per person
Jan 1 - Jan 6
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this motel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Price was $1,963, price is now $608 per person
$608
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We unfortunately came to stay when the staff decided to strike. No room service , no cleaning service for a 4 night stay. Barely got towels on the last day. Disappointing. The only upside was the location.

Reviewed on Oct 22, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $835, price is now $508 per person
$508
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $600, price is now $396 per person
$396
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
The location was perfect. I was there with “my girls”. My daughter and two grandchildren came from Michigan and I flew in from Florida to celebrate the youngest 21st birthday for the weekend. My other granddaughter lives in Chicago. We had a GREAT time! The only thing, which isn’t really important, is that we requested extra robes for pics, but they were not available.

Reviewed on Oct 24, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Price was $957, price is now $638 per person
$638
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Price was $651, price is now $440 per person
$440
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Buena ubicación y precio

Reviewed on Oct 24, 2026

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Price was $589, price is now $410 per person
$410
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 Chicago Riverwalk and Millennium Park are located nearby.
Great location and overall good stay. Hotel is a little tired and could have some maintenance improvements. Elevated noise on our room as well.

Reviewed on Oct 23, 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
Price was $1,368, price is now $953 per person
$953
per person
Dec 31 - Jan 3
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.

Oregon Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $600, price is now $396 per person
$396
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,963, price is now $608 per person
$608
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $835, price is now $508 per person
$508
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $664, price is now $425 per person
$425
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Oregon Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $663, price is now $382 per person
$382
per person
Jan 1 - Jan 6
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $780, price is now $409 per person
$409
per person
Jan 1 - Jan 6
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,024, price is now $606 per person
$606
per person
Jan 7 - Jan 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was $737, price is now $438 per person
$438
per person
Dec 25 - Dec 30
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Thu, Dec 10 - Mon, Dec 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$174 Roundtrip, found 8 hours ago
$174
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Dec 10 from Los Angeles Intl. to O'Hare Intl., returning Mon, Dec 14, priced at $174 found 8 hours ago
Delta
Mon, Dec 7 - Sat, Dec 12
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 14 hours ago
$206
Roundtrip
found 14 hours ago
Select Delta flight, departing Mon, Dec 7 from Los Angeles Intl. to O'Hare Intl., returning Sat, Dec 12, priced at $206 found 14 hours ago
Bargain Flight
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$258 Roundtrip, just found
$258
Roundtrip
just found
Select Bargain Flight flight, departing Thu, Nov 12 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 13, priced at $258 just found
Air China
Fri, Nov 13 - Fri, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,125 Roundtrip, found 12 hours ago
$1,125
Roundtrip
found 12 hours ago
Select Air China flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Fri, Nov 27, priced at $1,125 found 12 hours ago