Grayslake Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Grayslake Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Chicago Club Inn & Suites
Price was $616, price is now $538 per person
$538
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Westmont. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Ty Warner Park are located nearby.
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was $847, price is now $704 per person
$704
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Comfort Inn & Suites Geneva - West Chicago
Price was $678, price is now $581 per person
$581
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Geneva. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions American Science & Surplus Store and Fabyan Windmill are located nearby.
Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
Price was $876, price is now $771 per person
$771
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Wel located hotel. Clean. Helpful staff. Too bad they don't offer breakfast.
Reviewed on Nov 1, 2026
DoubleTree by Hilton Lisle Naperville
Price was $658, price is now $579 per person
$579
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Arrowhead Golf Club are located nearby.
Hollywood Casino Aurora
Price was $843, price is now $747 per person
$747
per person
Dec 24 - Dec 29
found 7 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Aurora. Enjoy a full-service spa, 9 restaurants, and a 24-hour fitness center. Popular attractions Chicago Premium Outlets and Funway Ultimate Entertainment Center are located nearby.
Top Hotel Deals
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
3.09 km from city center
Book a stay at this business-friendly hotel in Grayslake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
25.51 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
33.44 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 ...
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
28.16 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 ...
Quality Inn Schaumburg - Chicago near the Mall
600 North Martingale Rd Schaumburg IL
33.89 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 ...
Comfort Inn Chicago Schaumburg - O'Hare Airport
1300 E Higgins Rd Schaumburg IL
33.83 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. ...
Chez Hotel Arlington Heights
519 W Algonquin Rd Arlington Heights IL
33.32 km from city center
Stay at this hotel in Arlington Heights. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Embassy Suites by Hilton Chicago North Shore Deerfield
1445 Lake Cook Rd Deerfield IL
25.95 km from city center
Book a stay at this business-friendly hotel in Deerfield. Enjoy free breakfast, free parking, and free train station pick-up. Our guests praise the breakfast ...
Motel 6 Arlington Heights, IL - Chicago North Central
441 W Algonquin Rd Arlington Heights IL
33.47 km from city center
Stay at this motel in Arlington Heights. 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
32.43 km from city center
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 ...
Motel 6 Prospect Heights, IL
540 N Milwaukee Ave Prospect Heights IL
29.49 km from city center
Stay at this motel in Prospect Heights. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
8.85 km from city center
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
9.08 km from city center
Book a stay at this family-friendly resort in Gurnee. Enjoy 6 indoor pools, 5 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
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.
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$331 Roundtrip, found 2 days ago
$331
Roundtrip
found 2 days ago