Grayslake Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
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Grayslake Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
Downtown Evanston
Save 100% on your flight
Price was $850, price is now $551 per person
$551
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Evanston. 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 Clark Street Beach and Halim Time & Glass Museum are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $2,136, price is now $954 per person
$954
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Chicago (ORD)
Stay at this 4-star 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 Emily Hotel
Downtown Chicago
Price was $1,569, price is now $861 per person
$861
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star 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.
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Save 100% on your flight
Price was $1,014, price is now $571 per person
$571
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,491, price is now $945 per person
$945
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 5-star 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.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,301, price is now $838 per person
$838
per person
Oct 24 - Oct 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Top Hotel Deals
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road, Grayslake, IL
3.13 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 ...
Wyndham Garden Schaumburg Chicago Northwest
1725 E Algonquin Road, Schaumburg, IL
31.23 km from city center
Stay at this 3-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and a free area shuttle. Our guests praise the helpful staff and the ...
Hyatt Regency Schaumburg Chicago
1800 East Golf Rd, Schaumburg, IL
32.57 km from city center
Stay at this 4-star business-friendly hotel in Schaumburg. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
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 ...
Holiday Inn Express Chicago NW - Arlington Heights by IHG
2111 S Arlington Heights Rd, Arlington Heights, IL
33.46 km from city center
Stay at this hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Motel 6 Glenview, IL - Chicago North
1535 Milwaukee Ave, Glenview, IL
32.27 km from city center
Stay at this motel in Glenview. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the property condition in our ...
Embassy Suites by Hilton Chicago North Shore Deerfield
1445 Lake Cook Rd, Deerfield, IL
25.95 km from city center
Stay at this 4-star business-friendly hotel in Deerfield. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and ...
Motel 6 Prospect Heights, IL
540 N Milwaukee Ave, Prospect Heights, IL
29.48 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 ...
Hotel Indigo Chicago-Vernon Hills by IHG
450 N Milwaukee Ave, Vernon Hills, IL
14.59 km from city center
Stay at this 3.5-star boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr, Waukegan, IL
12.2 km from city center
Stay at this 3-star business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Express & Suites Prospect Heights by IHG
600 N Milwaukee Ave, Prospect Heights, IL
29.34 km from city center
Stay at this 3-star business-friendly hotel in Prospect Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd, Arlington Heights, IL
33.48 km from city center
Stay at this 3-star business-friendly hotel in Arlington Heights. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd, Gurnee, IL
8.9 km from city center
Stay at this 3-star business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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 27 - Sat, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 3 days ago
$145
Roundtrip
found 3 days ago
Sun, Sep 28 - Sat, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Wed, Oct 29 - Sun, Nov 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$174 Roundtrip, found 12 hours ago
$174
Roundtrip
found 12 hours ago
Tue, Nov 18 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Wed, Oct 29 - Sun, Nov 2
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 12 hours ago
$216
Roundtrip
found 12 hours ago