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The Revolution Hotel
South End
Save 100% on your flight
Price was $841, price is now $594 per person
$594
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9/10 Wonderful! (2,535 reviews)
Very reasonable cost but rooms are hit or miss. My room lacked window treatments to block out the outside light and was not well soundproofed so I heard the elevator and people talking outside all the time. The TV also didn’t work.
Positives are that the bedding is comfortable, the bathrooms are well maintained, the location is very convenient, and the gym is small but good.
Reviewed on Mar 20, 2026
Boston Harbor Hotel
North End
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Price was $2,357, price is now $1,451 per person
$1,451
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Excellent hotel- restaurants, room service, all of the staff, spacious room with view, bathroom amenities. Great location. Able to take a leisurely walk along the water, and close to many restaurants and theatre district. Also easy to catch a taxi or uber. Wonderful setting with water and city view. Will definitely return!
Reviewed on Mar 14, 2026
Centerboard
Nantucket Town
Save 100% on your flight
Price was $2,282, price is now $1,602 per person
$1,602
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (105 reviews)
There was hair on our bed, I ask for late due to getting dress for my wedding and I was told
Reviewed on Mar 20, 2026
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Check availability on hotels close to BackCountry Excursions
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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.