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YOTEL Boston

Seaport District

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per person

10 Sept - 13 Sept

found 23 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 23 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 23 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

Larz Anderson Park

Larz Anderson Park is just one of the places to see in Brookline, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed art galleries in this vibrant area.

Arnold Arboretum

Escape the city bustle and soak up the serenity in this beloved park that doubles as a respected Harvard University research center.

Samuel Adams Brewery

You can take time to visit Samuel Adams Brewery during your travels to Boston. Experience the fascinating museums or attend a sporting event in this vibrant area.

Forest Hills Cemetery

Step back in time and learn more about local history with a stop at Forest Hills Cemetery in Boston. Experience the acclaimed art galleries or attend a sporting event in this vibrant area.

Chestnut Hill Reservoir

Commune with nature and explore the great outdoors at Chestnut Hill Reservoir during your travels in Boston. Amble around this vibrant area's riverfront or attend a sporting event.

Larz Anderson Auto Museum

You can browse the exhibits at Larz Anderson Auto Museum, a museum with a storied past, during your holiday in Brookline. Experience the fascinating museums and acclaimed art galleries in this vibrant area.