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Grayslake Vacation Packages

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Grayslake Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

3 out of 5
per person
May 2 - May 4
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Stay at this 3-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 Michigan Avenue and Chicago Riverwalk are located nearby.
The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and Kohl Children's Museum are located nearby.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

3 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Soldier Field and Chicago Museum of Science and Industry are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
per person
Jun 13 - Jun 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hilton Garden Inn Chicago North Shore/Evanston

Hilton Garden Inn Chicago North Shore/Evanston

3.5 out of 5
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Evanston. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Aragon Ballroom and Riviera Theatre are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Save 100% on your flight
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Grayslake Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 23 - May 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 7 - Jun 10
found 6 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)

Grayslake Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Glen Club

The Glen Club

3.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 9
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 1 - May 7
found 8 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
The Chicago Hotel Collection River North

The Chicago Hotel Collection River North

3 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 3 - Jun 9
found 24 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 3 - Jun 9
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Apr 15 - Sat, Apr 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 15 from Los Angeles Intl. to O'Hare Intl., returning Sat, Apr 19, priced at $135 found 1 day ago
United
Wed, Apr 23 - Tue, Apr 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select United flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 29, priced at $181 found 2 days ago
American Airlines
Wed, Apr 23 - Tue, Apr 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Apr 23 from Los Angeles Intl. to O'Hare Intl., returning Tue, Apr 29, priced at $181 found 2 days ago
Hong Kong Airlines
Sun, Jun 29 - Sun, Jul 27
HKG
Hong Kong Intl.
ORD
O'Hare Intl.
$1,170 Roundtrip, found 6 days ago
$1,170
Roundtrip
found 6 days ago
Select Hong Kong Airlines flight, departing Sun, Jun 29 from Hong Kong Intl. to O'Hare Intl., returning Sun, Jul 27, priced at $1,170 found 6 days ago