Sheridan Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Sheridan Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,121, price is now CA $782 per person
CA $782
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Staff was very friendly and helpful. Room was clean. Free coffee and fruit in the AM.

Reviewed on Jul 9, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,834, price is now CA $1,264 per person
CA $1,264
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Nice hotel kind and fast staff

Reviewed on Jul 10, 2026

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,768, price is now CA $1,221 per person
CA $1,221
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
What a great excellent and friendly welcome front desk personnel. The lady on who worked on Saturday afternoon was amazing. Didn’t catch her name but she was very nice and welcoming

Reviewed on Jul 5, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,287, price is now CA $1,612 per person
CA $1,612
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 2026

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Sheridan Hotel Deals

Dog-Friendly Log Home On Fox River IL Near Starved Rock, Porch, Deck, Firepit

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

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Dog-Friendly Log Home On Fox River IL Near Starved Rock, Porch, Deck, Firepit
Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

3 out of 5
2643 IL-178 Utica IL
The price is CA $239 per night from Jul 14 to Jul 15
CA $239
CA $274 total
Jul 14 - Jul 15
includes taxes & fees
7.2/10 Good! (1,017 reviews)
"My grandkids enjoyed the water park. Nice staff and clean hotel."

Reviewed on Jul 10, 2026

Grand Bear Resort at Starved Rock
Best Western Oswego Hotel

Best Western Oswego Hotel

2.5 out of 5
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! (968 reviews)
"Great breakfast, parking lot safe"

Reviewed on Jul 6, 2026

Best Western Oswego Hotel
See all 377 properties in Sheridan
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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Stay near popular Sheridan attractions

Norway Motorsports Park

You can take time to visit Norway Motorsports Park during your travels to Norway.
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Frequently asked questions

How much does a Sheridan vacation package cost?
You'll find cheap prices from CA $782 on Expedia for your Sheridan getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Sheridan costs.
What are the cheapest months to go to Sheridan?
You can typically find lower prices and greater availability in November, December and January. Take a look at our cheap Sheridan vacation packages and you could get some excellent off-season deals.
How many days is enough for Sheridan?
With a well-organized travel plan, you can easily hit the most popular Sheridan sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Sheridan vacation for longer.
How to find the best Sheridan package deals?
Use Expedia's handy filters to find some great Sheridan package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Sheridan package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Sheridan vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Sheridan vacation by choosing your favourite type of stay, airline and car class.
How to plan a trip to Sheridan?

  1. Pick your dates: What you'd like to do in Sheridan and your favourite season can help you decide when to go.
  2. Set your budget: Factor in expenses such as flights, food and transportation when working out how much to set aside for your trip to Sheridan. Then, pick a hotel that matches your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Decide how long to go away for: Now that you're more familiar with Sheridan, you can figure out the ideal length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Sheridan vacation package.

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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.