Chequamegon Bay

Plan a trip to see Chequamegon Bay

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥329,330, price is now ￥257,722 per person
￥257,722
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Clean room and amenities

Reviewed on Jan 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥422,086, price is now ￥307,846 per person
￥307,846
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing

Reviewed on Jan 13, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was ￥446,626, price is now ￥344,356 per person
￥344,356
per person
Mar 27 - Mar 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.

Reviewed on Jan 5, 2026

Popular places to visit

StageNorth

You can enjoy a show at StageNorth during your stay in Washburn. Wander the lakeside in this family-friendly area.

StageNorth

Bayfield County Courthouse

Find out about the history of Washburn when you take a trip to Bayfield County Courthouse. Wander the lakeside in this family-friendly area.

Bayfield County Courthouse

Houghton Falls Nature Preserve

Explore the great outdoors at Houghton Falls Nature Preserve, a lovely green space in Washburn. Wander the lakeside in this family-friendly area.

Houghton Falls Nature Preserve

Ore Dock Park

Explore the great outdoors at Ore Dock Park, a lovely green space in Ashland. Wander the lakeside in this family-friendly area.

Ore Dock Park

Soo Line Locomotive 950

You can spend an afternoon browsing the exhibits at Soo Line Locomotive 950 during your travels in Ashland. Wander the lakeside in this family-friendly area.

Soo Line Locomotive 950

Ashland Mural Walk

Enjoy an outing to Ashland Mural Walk during your stay in Ashland. Wander the lakeside in this family-friendly area.

Ashland Mural Walk

Best Lodging Options Near Chequamegon Bay

Up North Oasis - Families & Dogs in the Bayfield Area

Up North Oasis - Families & Dogs in the Bayfield Area

Washburn WI
Up North Oasis - Families & Dogs in the Bayfield Area
Blue Wave Inn

Blue Wave Inn

3 out of 5
2521 Lake Shore Dr W Ashland WI
Blue Wave Inn
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles

Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles

Bayfield WI
Bayfield- Charming Newly Remodeled Condo, Gateway to Apostles
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows

Bayfield WI
Apostle Is.'s gateway/next scenic marinas/fireplace/jacuzzi/corner w 4 windows
See all 684 properties in Chequamegon Bay
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.