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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $573, price is now $377 per person
$377
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great extras Good location

Reviewed on Oct 16, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,119, price is now $652 per person
$652
per person
Dec 31 - Jan 5
found 11 hours 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 stay was all good as represented on the site!

Reviewed on Oct 12, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $892, price is now $521 per person
$521
per person
Dec 18 - Dec 23
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.

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $936, price is now $578 per person
$578
per person
Dec 3 - Dec 8
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.
It was an overnight stay for my birthday. The hotel was clean and the staff was friendly.

Reviewed on Oct 16, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Save 100% on your flight
Price was $1,037, price is now $659 per person
$659
per person
Nov 25 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Save 100% on your flight
Price was $639, price is now $408 per person
$408
per person
Dec 23 - Dec 26
found 2 days ago
Roundtrip flight included
Atlanta (ATL) 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.

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $866, price is now $574 per person
$574
per person
Dec 17 - Dec 20
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, 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.

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Save 100% on your flight
Price was $846, price is now $561 per person
$561
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Close to every things, great location

Reviewed on Oct 16, 2026

Grayslake Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $639, price is now $408 per person
$408
per person
Dec 23 - Dec 26
found 2 days 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 $754, price is now $487 per person
$487
per person
Dec 17 - Dec 20
found 10 hours 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 $745, price is now $490 per person
$490
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $866, price is now $574 per person
$574
per person
Dec 17 - Dec 20
found 8 hours 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 Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $803, price is now $477 per person
$477
per person
Dec 18 - Dec 23
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 $1,119, price is now $652 per person
$652
per person
Dec 31 - Jan 5
found 11 hours 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 $892, price is now $521 per person
$521
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $854, price is now $505 per person
$505
per person
Dec 18 - Dec 23
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.

Delta
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 4 from Los Angeles Intl. to O'Hare Intl., returning Mon, Nov 9, priced at $169 found 2 days ago
American Airlines
Tue, Nov 17 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 1 day ago
$178
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 17 from Los Angeles Intl. to O'Hare Intl., returning Thu, Nov 26, priced at $178 found 1 day ago
Frontier Airlines
Thu, Nov 26 - Fri, Nov 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 1 day ago
$193
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 26 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 27, priced at $193 found 1 day ago
Philippine Airlines
Fri, Nov 13 - Fri, Nov 27
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,074 Roundtrip, found 4 days ago
$1,074
Roundtrip
found 4 days ago
Select Philippine Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Fri, Nov 27, priced at $1,074 found 4 days ago