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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.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Save 100% on your flight
Price was $486, price is now $258 per person
$258
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Great location to shopping on State St and 1 mile away from the Chicago Riverwalk. Parking on State St and Harrison convenient and safe. Old building but well maintained. Bleach cleaned sheets and pillowcases. Pillows did not stink.Great smelling body wash, shampoo and conditioner in the shower. Had 2 double beds with microwave and small refrigerator.

Reviewed on Aug 9, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $4,896, price is now $2,857 per person
$2,857
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,167, price is now $713 per person
$713
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $2,946, price is now $1,800 per person
$1,800
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Save 100% on your flight
Price was $1,115, price is now $700 per person
$700
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good great i loved it

Reviewed on Aug 8, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,107, price is now $727 per person
$727
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Great staff, great place!

Reviewed on Aug 5, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,507, price is now $1,013 per person
$1,013
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $3,345, price is now $2,258 per person
$2,258
per person
Sep 13 - Sep 19
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
The only thing that was negative was it took forever to check in and limited parking by the lobby entrance.

Reviewed on Aug 7, 2026

Grayslake Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $688, price is now $424 per person
$424
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,167, price is now $713 per person
$713
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,115, price is now $700 per person
$700
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,302, price is now $818 per person
$818
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Grayslake Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $883, price is now $488 per person
$488
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,562, price is now $822 per person
$822
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,600, price is now $863 per person
$863
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,130, price is now $620 per person
$620
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

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

Frontier Airlines
Sat, Aug 22 - Sat, Sep 5
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$191 Roundtrip, found 7 hours ago
$191
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Aug 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 5, priced at $191 found 7 hours ago
American Airlines
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 11 hours ago
$197
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $197 found 11 hours ago
United
Wed, Nov 4 - Wed, Nov 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 11 hours ago
$197
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $197 found 11 hours ago
Hainan Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,131 Roundtrip, found 5 days ago
$1,131
Roundtrip
found 5 days ago
Select Hainan Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,131 found 5 days ago