Cambridge Vacation Packages
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Your Cambridge Vacation
Put together a custom vacation package to Cambridge and prepare to experience this amazing city on your own terms. Think about spending time in the neighborhood of Rockdale, which is great for watersports and tons more. Fill your spare time with visits to Cambridge Winery, Dancing Goat Distillery and Lake Ripley Park Beach, some of the top attractions you shouldn't miss during your trip to Cambridge. A couple of quick clicks is all it takes to build the perfect Cambridge vacation on Expedia.
Top Cambridge Vacation Deals
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,405, price is now CA $950 per person
CA $950
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities
Reviewed on May 3, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,919, price is now CA $1,699 per person
CA $1,699
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,741, price is now CA $1,702 per person
CA $1,702
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,495, price is now CA $1,049 per person
CA $1,049
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!
Reviewed on May 26, 2026
Cambridge Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from May 31 to Jun 1
CA $173
CA $199 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (3,798 reviews)
"This hotel was a great value!"
Reviewed on May 26, 2026
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jun 7 to Jun 8
CA $140
CA $161 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (1,011 reviews)
"The Doubletree was very nice. They, do, however need to repair their 3 elevator. We had fairly long waits."
Reviewed on May 26, 2026
The Edgewater
1001 Wisconsin Place Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from May 31 to Jun 1
CA $263
CA $339 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful hotel with an extremely helpful staff. We loved our stay."
Reviewed on May 25, 2026
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.
Discover the most popular places to visit in Cambridge
Lake Ripley Park Beach
Why not spend a carefree afternoon at Lake Ripley Park Beach during your travels in Lake Ripley? While you're in the area, wander around the parks.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
