
Chicago Beach Vacations
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Top Beach vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.

Renaissance Chicago North Shore Hotel
Price was ¥286,978, price is now ¥251,240 per person
¥251,240
per person
May 11 - May 18
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,001 reviews)
Room was decent. I couldn’t sleep though
Reviewed on Feb 17, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥346,605, price is now ¥266,562 per person
¥266,562
per person
May 20 - May 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥382,351, price is now ¥333,186 per person
¥333,186
per person
May 12 - May 16
found 3 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
The room was clean and tidy. There’s plenty of shops around and a 7-11 just across the street. Walking distance to Starbucks, Joe the juice, aldi and Joe’s trader.
Reviewed on Mar 7, 2026

Swissotel - Chicago
Downtown Chicago
Price was ¥431,924, price is now ¥381,564 per person
¥381,564
per person
May 12 - May 16
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (3,198 reviews)
Great location and a perfect-sized hotel for a stay in Chicago! Our room had a beautiful view and was quiet, clean, and comfortable, with lovely linens and a huge bathroom. The workout room on the top floor is spacious and offers another stellar view of the city. We also appreciated the cozy lobby, which was just the right size and included a nice lobby bar and an adjacent restaurant.
One of our favorite features was the pedway system, which made it easy to get around while staying warm. If you’re looking for a less crowded, very comfortable hotel with great views and close proximity to Michigan Avenue, the river, and the lake, this is a great choice. My only downside was the cost of parking and how tight and confusing it was to navigate the parking garage “underworld.”
Reviewed on Mar 6, 2026

Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was ¥295,938, price is now ¥263,058 per person
¥263,058
per person
May 20 - May 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,608 reviews)
We enjoyed our stay bar was closed our whole stay and cleaning lady was a bit rude but it may be due to language but overall great area to stay family friendly
Reviewed on Mar 3, 2026
5* Beach vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

3 Night Beach vacations in Chicago
Price found within the past 48 hours. Click for updated prices.


Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥376,543, price is now ¥356,946 per person
¥356,946
per person
Apr 16 - Apr 18
found 1 day ago
Roundtrip flight included
Singapore (SIN) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on Mar 3, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥377,830, price is now ¥364,513 per person
¥364,513
per person
Apr 16 - Apr 18
found 1 day ago
Roundtrip flight included
Singapore (SIN) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
We loved are stay at the Thompson hotel. It's very clean, and is close to our favorite shops and restaurants.
Reviewed on Mar 2, 2026
4 Night Beach vacations in Chicago
Price found within the past 48 hours. Click for updated prices.

Holiday Inn & Suites Chicago - Downtown by IHG
Downtown Chicago
Price was ¥295,648, price is now ¥263,658 per person
¥263,658
per person
May 12 - May 16
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.6/10 Excellent! (1,006 reviews)
Close to Union Station. Room size reasonable for city hotel.
Reviewed on Feb 21, 2026

Eurostars Magnificent Mile
Downtown Chicago
Price was ¥382,351, price is now ¥333,186 per person
¥333,186
per person
May 12 - May 16
found 3 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (3,285 reviews)
The room was clean and tidy. There’s plenty of shops around and a 7-11 just across the street. Walking distance to Starbucks, Joe the juice, aldi and Joe’s trader.
Reviewed on Mar 7, 2026

Swissotel - Chicago
Downtown Chicago
Price was ¥431,924, price is now ¥381,564 per person
¥381,564
per person
May 12 - May 16
found 4 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9/10 Wonderful! (3,198 reviews)
Great location and a perfect-sized hotel for a stay in Chicago! Our room had a beautiful view and was quiet, clean, and comfortable, with lovely linens and a huge bathroom. The workout room on the top floor is spacious and offers another stellar view of the city. We also appreciated the cozy lobby, which was just the right size and included a nice lobby bar and an adjacent restaurant.
One of our favorite features was the pedway system, which made it easy to get around while staying warm. If you’re looking for a less crowded, very comfortable hotel with great views and close proximity to Michigan Avenue, the river, and the lake, this is a great choice. My only downside was the cost of parking and how tight and confusing it was to navigate the parking garage “underworld.”
Reviewed on Mar 6, 2026
Top Beach Chicago Hotels

Millennium Knickerbocker Chicago
163 East Walton Place Chicago IL
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 ...
8.6/10 Excellent! (2,002 reviews)
The Knickerbocker is by fire one of our favorite places to stay. Perfect location to everything. They have the cutest martini bar in the lobby with great people that work there, and I always meet a fun new friend.
Reviewed on Mar 3, 2026

The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
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 ...
8.4/10 Very Good! (4,008 reviews)
Didnt like paying for parking and no gas stations close
Reviewed on Mar 5, 2026

Chicago Lake Shore Hotel
4900 S Lake Shore Dr Chicago IL
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.
6.8/10 (1,001 reviews)
Ants in the room and did get bit at night.
Reviewed on Feb 27, 2026
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.
