Galewood Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Galewood Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $610, price is now $436 per person
$436
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $941, price is now $541 per person
$541
per person
Nov 13 - Nov 17
found 19 hours ago
Roundtrip flight included
Denver (DEN) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,550, price is now $1,004 per person
$1,004
per person
Nov 13 - Nov 17
found 2 hours ago
Roundtrip flight included
Denver (DEN) 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 and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
La Banque Hotel
Save 100% on your flight
Price was $746, price is now $486 per person
$486
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $953, price is now $678 per person
$678
per person
Nov 13 - Nov 17
found 19 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $855, price is now $617 per person
$617
per person
Nov 19 - Nov 23
found 18 hours ago
Roundtrip flight included
Denver (DEN) 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.
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
15.11 km from Galewood
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Freehand Chicago
19 East Ohio Street, Chicago, IL
14.4 km from Galewood
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
14.33 km from Galewood
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
14.71 km from Galewood
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
14.4 km from Galewood
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
14.7 km from Galewood
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
14.71 km from Galewood
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
14.1 km from Galewood
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
14.61 km from Galewood
Stay at this 4-star family-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
14.71 km from Galewood
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 ...
The Wade
644 N Lake Shore Dr, Chicago, IL
15.35 km from Galewood
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
14.42 km from Galewood
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street, Chicago, IL
14.72 km from Galewood
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff ...
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.
Thu, Oct 2 - Sat, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 6 days ago
$145
Roundtrip
found 6 days ago
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$161 Roundtrip, found 6 days ago
$161
Roundtrip
found 6 days ago
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$170 Roundtrip, found 6 days ago
$170
Roundtrip
found 6 days ago
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Wed, Oct 29 - Sat, Nov 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago