Rosewood Beach

Beautiful little cove in any season!
Beautiful little cove in any season!
Lake Michigan is always unforgettable.
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 S$1,391, price is now S$803 per person
S$803
per person
23 Apr - 26 Apr
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The service was excellent, the rooms were clean and comfortable, and the breakfast buffet was also good. The bar in the lobby also served the best cocktails we had on the entire trip. The location was AMAZING, right off of Magnificent Mile! We were within 12 minutes walking time to 95% of the places we wanted to go. This hotel is great value for money.

Reviewed on 20 Feb, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,704, price is now S$1,223 per person
S$1,223
per person
23 Apr - 26 Apr
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks

Reviewed on 17 Feb, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was S$1,266, price is now S$917 per person
S$917
per person
23 Apr - 26 Apr
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Nice hotel Great location

Reviewed on 15 Feb, 2026

Popular places to visit

Summer night at Ravinia means music, picnic food, and wine!

Ravinia Park

Ravinia Park is just one of the places to see in Highland Park, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Ravinia Park
At the garden..

Chicago Botanic Garden

Explore the great outdoors at Chicago Botanic Garden, a lovely green space in Chicago. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Chicago Botanic Garden
Inside a Box of Chocolates

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Chocolate Box
People, golf cart and outside course in nature, happy and relax in transport path or country club hobby on weekend break. Fitness, driving and smile for sport game conversation, golfers and together

Sportsman's Country Club

Enjoy a round of golf in Northbrook at Sportsman's Country Club. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Sportsman's Country Club

Ravinia Pavilion

You can enjoy a show at Ravinia Pavilion during your trip to Highland Park. Wander around the area's picturesque gardens or experience its great live music.

Ravinia Pavilion

Debbie Gottlieb Beitler Dog Park

Debbie Gottlieb Beitler Dog Park is just one of the places to see in Highland Park, so why not enjoy the other things to explore during your travels? Discover the restaurants and live music in this family-friendly area.

Debbie Gottlieb Beitler Dog Park

Top Rosewood Beach Hotel Deals

Courtyard by Marriott Chicago Highland Park/Northbrook

Courtyard by Marriott Chicago Highland Park/Northbrook

3 out of 5
1505 Lake Cook Road Highland Park IL
Courtyard by Marriott Chicago Highland Park/Northbrook
Renaissance Chicago North Shore Hotel

Renaissance Chicago North Shore Hotel

4 out of 5
933 Skokie Blvd Northbrook IL
Renaissance Chicago North Shore Hotel
Super 8 by Wyndham Deerfield/Northbrook

Super 8 by Wyndham Deerfield/Northbrook

2.5 out of 5
340 South Waukegan Road Deerfield IL
Super 8 by Wyndham Deerfield/Northbrook
Residence Inn By Marriott Chicago Deerfield

Residence Inn By Marriott Chicago Deerfield

3 out of 5
530 Lake Cook Rd Deerfield IL
Residence Inn By Marriott Chicago Deerfield
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd Deerfield IL
Hyatt Regency Deerfield
Courtyard by Marriott Chicago Deerfield

Courtyard by Marriott Chicago Deerfield

3 out of 5
800 Lake Cook Rd Deerfield IL
Courtyard by Marriott Chicago Deerfield
Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield

4 out of 5
1445 Lake Cook Rd Deerfield IL
Embassy Suites by Hilton Chicago North Shore Deerfield
Sheraton Chicago Northbrook Hotel

Sheraton Chicago Northbrook Hotel

3.5 out of 5
1110 Willow Rd Northbrook IL
Sheraton Chicago Northbrook Hotel
Staybridge Suites Chicago - Glenview by IHG

Staybridge Suites Chicago - Glenview by IHG

3 out of 5
2600 Lehigh Ave Glenview IL
Staybridge Suites Chicago - Glenview by IHG
See all 591 properties in Rosewood Beach
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.

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Book now

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.