Sheridan Vacation Packages
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Top Sheridan Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,161, price is now CA $787 per person
CA $787
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 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
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
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
Sheridan Hotel Deals
Dog-Friendly Log Home On Fox River IL Near Starved Rock, Porch, Deck, Firepit
Sheridan IL
9.8/10 Exceptional! (178 reviews)
"Place was very welcoming to to the pets along with the humans. Would highly recommend."
Reviewed on Mar 22, 2026
Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
The price is CA $192 per night from Jun 1 to Jun 2
CA $192
CA $219 total
Jun 1 - Jun 2
includes taxes & fees
7.2/10 Good! (1,005 reviews)
"I just loved it and so did my family the weather was perfect rhe indoor water park was cool my kids loved being in there the place was very clean the food was very good the rooms were perfect for my family and the beds were so comfortable the staff was very very nice we really had a great time there ..."
Reviewed on May 26, 2026
Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Jun 14 to Jun 15
CA $120
CA $131 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (913 reviews)
"Room was great for the price, but like most hotels since Covid, breakfast is not up to par. I know it’s free, but at least make it tasty, enticing and a variety, not just pork, some of us don’t eat beef or pork. But overall good rooms and stay was great."
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.
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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.
