Chicago Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon

    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Beach Chicago Hotels

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
163 East Walton Place, Chicago, IL
  • 9 min drive from Wrigley Field
Recharge at this hotel and get ready to stroll along the shore in Chicago, as you'll be near Oak Street Beach. Amenities at Millennium Knickerbocker Chicago ...
Millennium Knickerbocker Chicago
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
  • 9 min drive from Wrigley Field
Enjoy sunsets on the beach in Chicago, as you'll be a short walk from Oak Street Beach with a vacation at this boutique hotel. A restaurant and a bar are just ...
8.2/10 Very Good! (3,409 reviews)
"Great location but breakfast is poor."

Reviewed on 2025/8/30

The Whitehall Hotel, BW Premier Collection
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr, Chicago, IL
  • 25 min drive from Wrigley Field
Settle in and relax at this hotel and get ready to lounge by the shoreline in Chicago, as you'll be close to the beach.
Chicago Lake Shore Hotel
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.