
Gilberts Vacations
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Gilberts Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
$458
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
The pictures match the rooms. The hotel staff was polite and pleasant and very helpful.
Reviewed on Aug 23, 2026

Level Chicago Fulton Market
Downtown Chicago
$731
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room
Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day
As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them.
For the money your room key or a key pad should allow you in.
Reviewed on Aug 21, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
$654
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) 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.

Level Chicago – Old Town
Downtown Chicago
$627
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$494
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Stay at this 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.
Perfect location. Staff was friendly & accommodating.
Reviewed on Aug 23, 2026

River Hotel
Downtown Chicago
$462
per person
Oct 26 - Oct 30
found 22 hours ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Book a stay at this business-friendly 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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
To be honest, we only used the hotel facilities for the basics; the staff was always attentive, and the hotel was in excellent condition. However, the standout feature is its prime location—right in the heart of downtown Chicago—with great connections to all the major tourist attractions to walking distance.
Reviewed on Aug 23, 2026
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 ...

Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...

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 ...

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. ...

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 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 ...

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 ...

Days Inn & Suites by Wyndham Arlington Heights
1415 W Dundee Rd Arlington Heights IL
Book a stay at this business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...

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 ...

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 ...

Renaissance Schaumburg Convention Center Hotel
1551 Thoreau Dr N Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff ...

Marriott Chicago Schaumburg
50 N Martingale Rd Schaumburg IL
Book a stay at this business-friendly hotel in Schaumburg. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. 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 ...

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 ...

Extended Stay America Suites Chicago Schaumburg I90
2000 N Roselle 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 ...
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 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 14 hours ago

Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$173
Roundtrip
found 14 hours ago

Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 14 hours ago

Tue, Oct 20 - Sat, Nov 7
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 17 hours ago

Tue, Sep 29 - Sat, Oct 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$317
Roundtrip
found 3 days ago
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