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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,695, price is now $1,062 per person
$1,062
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,974, price is now $1,161 per person
$1,161
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Stay at this 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,502, price is now $1,608 per person
$1,608
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
The hotel is beautiful. It has an amazing breakfast buffet, an amazing terrace with great drinks. The staff is super helpful and friendly. This hotel is a 10/10 for sure!
Reviewed on Aug 5, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,873, price is now $1,229 per person
$1,229
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,908, price is now $1,305 per person
$1,305
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this 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.
Everything was great.
Reviewed on Aug 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,749, price is now $1,224 per person
$1,224
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
N/A
Reviewed on Aug 5, 2026
Top Hotel Deals
Eaglewood Resort and Spa
1401 Nordic Rd Itasca IL
32.09 km from city center
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 ...
The Westin Chicago Northwest
400 Park Blvd Itasca IL
31.95 km from city center
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 ...
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road Schaumburg IL
27.95 km from city center
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 ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd Schaumburg IL
27.63 km from city center
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
27.89 km from city center
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
28.4 km from city center
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
28.52 km from city center
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
30.53 km from city center
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
28.49 km from city center
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
30.87 km from city center
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 ...
Hilton Garden Inn Hoffman Estates
2425 Barrington Road Hoffman Estates IL
19.22 km from city center
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 ...
Marriott Chicago Schaumburg
50 N Martingale Rd Schaumburg IL
29.15 km from city center
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 ...
Best Western Plus Elgin - Chicago
2175 Marriott Dr West Dundee IL
7.75 km from city center
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 ...
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, Sep 5 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 2 days ago
$178
Roundtrip
found 2 days ago
Sun, Sep 13 - Sat, Sep 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Wed, Sep 16 - Sun, Sep 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$346 Roundtrip, found 1 day ago
$346
Roundtrip
found 1 day ago