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Top Sheridan Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was CA $1,372, price is now CA $969 per person
CA $969
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The rooms were spotless and very well tended to. My wife and I really enjoyed how central it was to many stores, restaurants, and places of interest. We also enjoyed the bar, with its selection of great drinks; it was a great way to relax after walking around Chicago all day!
Reviewed on Jul 4, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $1,606, price is now CA $1,064 per person
CA $1,064
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,895, price is now CA $1,263 per person
CA $1,263
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $2,573, price is now CA $1,809 per person
CA $1,809
per person
Aug 7 - Aug 11
found 21 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026

The Langham, Chicago
Downtown Chicago
Price was CA $2,734, price is now CA $1,987 per person
CA $1,987
per person
Sep 4 - Sep 7
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Everything was mostly great. Except it was a bit overpriced (especially the spa) and minibar person kept adding stuff I didn't use to my bill. Also they don't tell you what perks you have depending on your reservation. You have to ask. Also I stayed in a junior suite for 8 days and they wouldn't give me a late check out. Finally, they begrudgingly have me an hour after I reminded them I spent almost $9,000 dollars there. Gee, thanks. Front desk guy at check in was mostly unhelpful although he was friendly and polite. Tons of great stuff.
Reviewed on Jul 2, 2026
Sheridan Hotel Deals

Dog-Friendly Log Home On Fox River IL Near Starved Rock, Porch, Deck, Firepit
Sheridan IL
10/10 Exceptional! (182 reviews)
"Loved this place so much! It was well appointed, comfortable, clean and communication with Candace was easy. Watching the hummingbirds on the front porch was so relaxing and we all loved the space. I’d come back again in a heartbeat."
Reviewed on Jun 14, 2026

Grand Bear Resort at Starved Rock
2643 IL-178 Utica IL
The price is CA $240 per night from Jul 8 to Jul 9
CA $240
CA $274 total
Jul 8 - Jul 9
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"We had a wonderful experience. Thank you."
Reviewed on Jul 3, 2026

Best Western Oswego Hotel
2055 Wiesbrook Dr Oswego IL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Jul 26 to Jul 27
CA $124
CA $135 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (960 reviews)
"Friendly front staff, clean rooms, descent breakfast options."
Reviewed on Jul 3, 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.







