Gilberts Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Gilberts Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$542
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Check-in and check-out were a breeze. Very clean rooms, spacious bathroom. The room was smaller than expected, but perfect for my solo trip. Convenient location, 15 min walk from the river area, 8 min from the Michigan blvd. Aldi 5 min away, Starbuck 2 min away, Wallgreens 2 min away. Seemed pretty safe at night.
Reviewed on Sep 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$875
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.
Great location. So much to do in walking distance and hotel was great.
Reviewed on Sep 16, 2026
The Emily Hotel
Downtown Chicago
$717
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 United Center and Chicago Riverwalk are located nearby.
Comfortable room with a great view and luxuriously soft bed!
Reviewed on Sep 13, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
$750
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 Millennium Park and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
$869
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Clean room, nice location
Reviewed on Sep 15, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,364
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Fresno (FAT) 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.
Top Hotel Deals
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in ...
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
The Westin Chicago Northwest
400 Park Blvd Itasca IL
Book a stay at this business-friendly hotel in Itasca. Enjoy breakfast (surcharge), a free area shuttle, and a 24-hour fitness center. Our guests praise the ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
Stay at this motel in Rolling Meadows. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
Hyatt Place Chicago/ Schaumburg
1851 McConnor Parkway Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Plus Elgin - Chicago
2175 Marriott Dr West Dundee IL
Book a stay at this business-friendly hotel in West Dundee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Red Roof Inn PLUS+ Chicago - Hoffman Estates
2500 Hassell Road Hoffman Estates IL
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
Hilton Garden Inn Hoffman Estates
2425 Barrington Road Hoffman Estates IL
Book a stay at this business-friendly hotel in Hoffman Estates. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff ...
Hampton Inn Chicago-Carol Stream
205 W North Ave Carol Stream IL
Stay at this hotel in Carol Stream. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Motel 6 Elk Grove Village, IL
1000 W Devon Ave Elk Grove Village IL
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
Country Inn & Suites by Radisson, Schaumburg, IL
1401 North Roselle Road Schaumburg IL
Book a stay at this family-friendly hotel in Schaumburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Country Inn & Suites by Radisson, Elk Grove Village/Itasca
1160 W Devon Avenue Elk Grove Village IL
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
Baymont By Wyndham Schaumburg Chicago Northwest
1725B E Algonquin Rd Schaumburg IL
Stay at this hotel in Schaumburg. Enjoy free parking, a 24-hour front desk, and an airport shuttle (surcharge). Popular attractions Woodfield Mall and Topgolf ...
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.
Sat, Oct 10 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$159
Roundtrip
found 5 days ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$206
Roundtrip
found 9 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$215
Roundtrip
found 9 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216
Roundtrip
found 9 hours ago
Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$217
Roundtrip
found 9 hours ago
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