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YOTEL Boston

Seaport District

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per person

10 Sept - 13 Sept

found 13 hours 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 13 hours 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 13 hours 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

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Boston Old Town Trolley Hop-on Hop-Off City Tour

Free cancellation available

Private & custom tours

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North End Boston Mafia Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

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Boston to Martha's Vineyard with Optional Island Tour

Free cancellation available

Attractions

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Boston CityPASS®: Admission to Top 4 Attractions

Free cancellation available

Adventure & outdoor

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Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

Popular places to visit

Coolidge Corner Theatre

Enjoy a performance at Coolidge Corner Theatre, a theatre with a story to tell in Brookline. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Frederick Law Olmsted National Historic Site

You can find out about the history of Brookline with a stop at Frederick Law Olmsted National Historic Site. Experience the fascinating museums or attend a sporting event in this vibrant area.

Griggs Park Green Dog Park

After visiting Griggs Park Green Dog Park, make a plan to see the other sights and activities in Brookline.

Brookline Farmers Market

Enjoy an outing to Brookline Farmers Market during your stay in Brookline. Experience the acclaimed theatre scene or attend a sporting event in this vibrant area.