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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug. 29, 2025
Pendry Chicago
Downtown Chicago
Price was CA $1,375, price is now CA $820 per person
CA $820
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on Aug. 26, 2025
The Emily Hotel
Downtown Chicago
Price was CA $2,190, price is now CA $1,400 per person
CA $1,400
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug. 22, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,133, price is now CA $740 per person
CA $740
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent
Reviewed on Aug. 21, 2025
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 $172 per night from Aug 31 to Sep 1
CA $172
CA $199 total
Aug 31 - Sep 1
includes taxes & fees
DoubleTree by Hilton Madison East
4402 E Washington Ave, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Aug 31 to Sep 1
CA $162
CA $188 total
Aug 31 - Sep 1
includes taxes & fees
La Quinta Inn & Suites by Wyndham Madison American Center
5217 E Terrace Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Sep 14 to Sep 15
CA $104
CA $120 total
Sep 14 - Sep 15
includes taxes & fees
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.