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.
Motel Edgebrook Chicago North Shore by OYO
Forest Glen
Price was $416, price is now $344 per person
$344
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Allstate Arena and Milwaukee Avenue are located nearby.
Rainbow Motel
Garfield Ridge
Price was $475, price is now $384 per person
$384
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Stay at this motel in Chicago. Enjoy free WiFi, free parking, and room service. Popular attraction SeatGeek Stadium is located nearby.
Sleep Inn Midway Airport Bedford Park
Bedford Park
Price was $461, price is now $398 per person
$398
per person
Nov 8 - Nov 11
found 22 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 a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attraction SeatGeek Stadium is located nearby.
Admiral Motel By Oyo Chicago I-94
Chatham
Price was $425, price is now $377 per person
$377
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Chicago Museum of Science and Industry and Jackson Park are located nearby.
Best Motel By OYO Chicago I-90
Woodlawn
Price was $411, price is now $368 per person
$368
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Stay at this property in Chicago. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Chicago Museum of Science and Industry are located nearby.
Capital O Empire Motel Chicago I-94
Greater Grand Crossing
Price was $382, price is now $346 per person
$346
per person
Nov 8 - Nov 11
found 22 hours ago
Roundtrip flight included
Portland (PDX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attractions Chicago Museum of Science and Industry and Rate Field 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