Hillsdale Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Hillsdale Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was $1,462, price is now $1,220 per person
$1,220
per person
Dec 19 - Dec 25
found 2 hours ago
Roundtrip non-stop 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,836, price is now $1,397 per person
$1,397
per person
Dec 19 - Dec 25
found 2 hours ago
Roundtrip non-stop 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.
1
Reviewed on Nov 4, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,845, price is now $2,229 per person
$2,229
per person
Dec 19 - Dec 25
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,739, price is now $1,385 per person
$1,385
per person
Dec 19 - Dec 25
found 2 hours ago
Roundtrip non-stop flight included
Portland (PDX) 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.
This is my 3rd time staying at Eurostars and it was excellent as it always has been! Clean rooms, I appreciate the overnight valet, and it is in a great/safe location.
Reviewed on Nov 4, 2026
Swissotel - Chicago
Downtown Chicago
Price was $1,673, price is now $1,370 per person
$1,370
per person
Dec 19 - Dec 25
found 2 hours ago
Roundtrip non-stop 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.
Breakfast was good
Reviewed on Nov 4, 2026
Top Hotel Deals
Wyndham Moline on John Deere Commons
1415 River Dr Moline IL
31.11 km from city center
Book a stay at this business-friendly hotel in Moline. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...
DoubleTree by Hilton Davenport
111 E 2nd St Davenport IA
34.89 km from city center
Book a stay at this business-friendly hotel in Davenport. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our ...
Isle Casino Hotel Bettendorf - A Caesars Rewards Destination
1777 Isle Pkwy Bettendorf IA
29.57 km from city center
Book a stay at this business-friendly hotel in Bettendorf. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms ...
Comfort Inn & Suites Davenport - Quad Cities
8300 Northwest Boulvard Davenport IA
37.73 km from city center
Book a stay at this business-friendly hotel in Davenport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hotel Blackhawk, Autograph Collection
200 E 3rd St Davenport IA
34.78 km from city center
Book a stay at this luxury hotel in Davenport. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
Stoney Creek Hotel Quad Cities - Moline
101 18th St Moline IL
30.68 km from city center
Book a stay at this business-friendly hotel in Moline. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
La Quinta Inn by Wyndham Davenport & Conference Center
3330 E Kimberly Rd Davenport IA
29.9 km from city center
Book a stay at this business-friendly hotel in Davenport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Days Inn By Wyndham Davenport
400 Jason Way Ct Suite DA Davenport IA
32.87 km from city center
Book a stay at this business-friendly hotel in Davenport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Hyatt House East Moline Quad Cities
111 Bend Blvd East Moline IL
25.77 km from city center
Book a stay at this business-friendly hotel in East Moline. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Our guests praise the helpful staff and the ...
Rhythm City Casino Resort
7077 Elmore Ave. Davenport IA
29.84 km from city center
Book a stay at this spa hotel in Davenport. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Comfort Inn Davenport East - Bettendorf
3206 E Kimberly Rd Davenport IA
30.04 km from city center
Book a stay at this business-friendly hotel in Davenport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The TBK Bank Sports Complex ...
Ramada by Wyndham Bettendorf
3020 Utica Ridge Rd Bettendorf IA
29.5 km from city center
Book a stay at this business-friendly hotel in Bettendorf. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The TBK Bank Sports Complex ...
Sleep Inn & Suites Davenport - Quad Cities
5350 Elmore Ave Davenport IA
29.87 km from city center
Book a stay at this business-friendly hotel in Davenport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Sun, Nov 15 - Sat, Nov 21
DEN
Denver Intl.
MLI
Quad City Intl.
$369 Roundtrip, found 5 days ago
$369
Roundtrip
found 5 days ago
Tue, Nov 17 - Fri, Dec 4
DEN
Denver Intl.
MLI
Quad City Intl.
$379 Roundtrip, found 5 days ago
$379
Roundtrip
found 5 days ago
Sun, Nov 15 - Sat, Nov 21
DEN
Denver Intl.
MLI
Quad City Intl.
$379 Roundtrip, found 5 days ago
$379
Roundtrip
found 5 days ago
Sat, Nov 21 - Fri, Dec 4
DEN
Denver Intl.
MLI
Quad City Intl.
$399 Roundtrip, found 5 days ago
$399
Roundtrip
found 5 days ago