Gross Point Vacations from $494
Book a Hotel + Flight or Car together to unlock savings
The Latest Gross Point Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Riu Plaza Chicago
Sep 3 - Sep 5Hotel Riu Plaza Chicago + Flight
Downtown Chicago2 nights4.0 star property9.4/10 - Exceptional (4,874 reviews)"I had an amazing experience. The room was very clean with a comfy bed. The staff, especially Alan, was very helpful. He was patient and supportive."Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago Fulton Market
Oct 15 - Oct 19Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (542 reviews)"Comes with all the comforts of Home."Reviewed July 29, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Felix River North/Magnificent Mile
Sep 3 - Sep 6Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.2/10 - Very Good (2,879 reviews)"Great location"Reviewed July 31, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Oct 15 - Oct 19Level Chicago – Old Town + Flight
Downtown Chicago4 nights4.0 star property9.0/10 - Wonderful (512 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Oct 7 - Oct 11Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights4.0 star property9.4/10 - Exceptional (2,621 reviews)"Nice location."Reviewed July 31, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop
Gross Point Hotel Deals
Holiday Inn Express & Suites Prospect Heights by IHG
Holiday Inn Express & Suites Prospect Heights by IHG3.0 star property
8.8 mi from Gross Point
9.0 out of 10, Wonderful, (1,019 reviews)
9.0/10
Wonderful
(1,019 reviews)
"Great staff with a delicious breakfast"
$106 nightly
The price is $119
$119 total
Aug 30 - Aug 31
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold Coast4.0 star property
12.8 mi from Gross Point
8.0 out of 10, Very Good, (1,867 reviews)
8.0/10
Very Good
(1,867 reviews)
"Good"
$152 nightly
The price is $181
$181 total
Aug 11 - Aug 12
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton4.0 star property
14.2 mi from Gross Point
9.4 out of 10, Exceptional, (2,621 reviews)
9.4/10
Exceptional
(2,621 reviews)
"Nice location."
$215 nightly
The price is $256
$256 total
Aug 30 - Aug 31
Total with taxes and fees
Claridge House Chicago, Tapestry Collection by Hilton
Claridge House Chicago, Tapestry Collection by Hilton4.0 star property
12.8 mi from Gross Point
9.0 out of 10, Wonderful, (1,454 reviews)
9.0/10
Wonderful
(1,454 reviews)
"We love staying at the Claridge! Our go to hotel in downtown Chicago. The location is great, the staff is friendly and helpful and the rooms are clean and comfortable."
$155 nightly
The price is $184
$184 total
Aug 30 - Aug 31
Total with taxes and fees
7.8 out of 10, Good, (3,256 reviews)
7.8/10
Good
(3,256 reviews)
$119 nightly
The price is $142
$142 total
Aug 31 - Sep 1
Total with taxes and fees
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites3.5 star property
13.3 mi from Gross Point
9.0 out of 10, Wonderful, (4,684 reviews)
9.0/10
Wonderful
(4,684 reviews)
$161 nightly
The price is $191
$191 total
Aug 30 - Aug 31
Total with taxes and fees
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The Loop4.0 star property
14.3 mi from Gross Point
9.4 out of 10, Exceptional, (1,157 reviews)
9.4/10
Exceptional
(1,157 reviews)
$176 nightly
The price is $209
$209 total
Aug 30 - Aug 31
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.