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YOTEL Boston

Seaport District

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per person

10 Sept - 13 Sept

found 1 day ago

Return flight included

Chicago (ORD) to Boston (BOS)

8.6/10 Excellent! (2,098 reviews)

Located in a new neighborhood with lots of dining options and easy access to public transportation.

Reviewed on 28 Jul 2025

Boston Harbor Hotel

North End

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per person

10 Sept - 13 Sept

found 1 day ago

Return flight included

Chicago (ORD) to Boston (BOS)

9.8/10 Exceptional! (1,018 reviews)

I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Back Bay

Save 100% on your flight

per person

10 Sept - 13 Sept

found 1 day ago

Return flight included

Chicago (ORD) to Boston (BOS)

9.6/10 Exceptional! (122 reviews)

Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

Tours & day trips

See all 64 activities

Portland: Best of Maine Lighthouse Scenic Cruise

Free cancellation available

Food, drink & nightlife

See all 15 activities

Portland: Casco Bay Sunset and Lighthouse Cruise

Free cancellation available

Private & custom tours

See all 9 activities

City centre Golden Adventure Quest Experience in Portland

Free cancellation available

Adventure & outdoor

See all 5 activities

Around The Peninsula Bike Tour

Free cancellation available

Holiday & seasonal tours

See all 3 activities

Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks

Free cancellation available

Popular places to visit

Bug Light

You can find out about the history of South Portland with a trip to Bug Light. Experience the area's great live music and acclaimed theatre scene.

Fort Preble

On the South Portland waterfront, survey the scene of the Battle of Portland Harbor, which is the only known Civil War conflict fought in Maine.

Southern Maine Community College

Walk around the campus at Southern Maine Community College during your visit to South Portland. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Spring Point Ledge Lighthouse

Find out about the history of South Portland when you take a trip to Spring Point Ledge Lighthouse. Experience the area's great live music and acclaimed theatre scene.

Maine Jewish Museum

Located in the immigrant-era Etz Chaim Synagogue, this museum tells the stories of Maine’s Jewish families and showcases Jewish artists from the area.

Portland Observatory

You can find out about the history of Portland with a stop at Portland Observatory. Stroll along the area's seaside or experience its acclaimed theatre scene.