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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $665, price is now $530 per person
$530
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Roman everything was clean everything was made that was all and it was very
Reviewed on Nov 4, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,033, price is now $731 per person
$731
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) 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.
1
Reviewed on Nov 4, 2026
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was $974, price is now $703 per person
$703
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Downtown Chicago
Price was $833, price is now $650 per person
$650
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Breakfast was good
Reviewed on Nov 4, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was $727, price is now $572 per person
$572
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this luxury 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.
Eurostars Magnificent Mile
Downtown Chicago
Price was $822, price is now $676 per person
$676
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Little Rock (LIT) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
This is my 3rd time staying at Eurostars and it was excellent as it always has been! Clean rooms, I appreciate the overnight valet, and it is in a great/safe location.
Reviewed on Nov 4, 2026
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 5 days ago
$237
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$237 Roundtrip, found 5 days ago
$237
Roundtrip
found 5 days ago
Thu, Dec 17 - Fri, Dec 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$331 Roundtrip, found 5 days ago
$331
Roundtrip
found 5 days ago