Sterling Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Sterling Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$801
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Room was not up to par, bad smell, stains on white bedding, and bathroom
Contacted management and front desk they made me wait 7 hours for them to come change sheets and did not provide an alternate room.
Reviewed on Oct 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$910
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip flight included
Portland (PDX) 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.
Hotel, accommodations, amenities, and staff were all amazing!
Reviewed on Oct 4, 2026
Level Chicago Fulton Market
Downtown Chicago
$928
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip flight included
Portland (PDX) 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.
The Talbott, Autograph Collection
Downtown Chicago
$935
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this luxury 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.
Swissotel - Chicago
Downtown Chicago
$931
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip flight included
Portland (PDX) 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.
Good hotel in a good location but starting to show its age
Reviewed on Oct 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$1,085
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Top Hotel Deals
Country Inn & Suites by Radisson, Rock Falls, IL
2106 First Avenue Rock Falls IL
Book a stay at this business-friendly hotel in Rock Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Fairfield By Marriott Inn & Suites Dixon
1755 Fulfs Lane Dixon IL
Book a stay at this business-friendly hotel in Dixon. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Ronald Reagan Boyhood ...
Tru By Hilton Dixon
1806 S. Galena Ave Dixon IL
Stay at this hotel in Dixon. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Popular attractions Ronald Reagan Boyhood Home and John Deere ...
Candlewood Suites Dixon by IHG
136 Plaza Dr Dixon IL
Stay at this hotel in Dixon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Ronald ...
Super 8 by Wyndham Rock Falls Sterling Area
2100 1st Ave Rock Falls IL
Stay at this motel in Rock Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
White Pines Lodge
6712 W Pines Rd. Mount Morris IL
Stay at this hotel in Mount Morris. Enjoy free parking, housekeeping, and a restaurant. Popular attractions White Pines Forest State Park and Dillehay Park are ...
Holiday Inn Express & Suites Rock Falls by IHG
301 E 2nd St Rock Falls IL
Book a stay at this business-friendly hotel in Rock Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sinnissippi Park and Westwood ...
Super 8 by Wyndham Dixon
1800 S Galena Ave Dixon IL
Book a stay at this business-friendly hotel in Dixon. Enjoy free breakfast, free parking, and a 24-hour front desk. Popular attractions Ronald Reagan Boyhood ...
Rockfalls Inn & Suite
2105 1st Ave Rock Falls IL
Book a stay at this business-friendly hotel in Rock Falls. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Sinnissippi Park and Westwood ...
Holiday Inn Express Dixon By Ihg
136 Plaza Dr Suite B Dixon IL
Stay at this hotel in Dixon. Enjoy free breakfast. Popular attractions Ronald Reagan Boyhood Home and John Deere Historic Site are located nearby.
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.
Mon, Oct 12 - Mon, Nov 2
MSP
Minneapolis - St. Paul Intl.
PIA
Greater Peoria Regional
$354
Roundtrip
found 4 days ago
Sat, Dec 26 - Tue, Jan 5
LAX
Los Angeles Intl.
PIA
Greater Peoria Regional
$379
Roundtrip
found 1 day ago
Tue, Mar 23 - Mon, May 24
LAX
Los Angeles Intl.
PIA
Greater Peoria Regional
$414
Roundtrip
found 1 hour ago
Tue, Oct 6 - Tue, Oct 13
ATL
Hartsfield-Jackson Atlanta Intl.
MLI
Quad City Intl.
$569
Roundtrip
found 4 hours ago
Best points of interest in Sterling
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