Sheridan Vacations from $235

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The Latest Sheridan vacation packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $391, price is now $235 per person
$235
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,241 reviews)
Great property and room

Reviewed on Dec 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $956, price is now $555 per person
$555
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Absolutely loved the hotel.Grand Dulxe Suite was huge with amazing views.All staff top notch.

Reviewed on Dec 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $533, price is now $313 per person
$313
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was very nice. Will book again on a future visit!

Reviewed on Dec 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $612, price is now $362 per person
$362
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
A very clean room, everything smells good and fresh, very nice staff, the staff helps all the time, my family and I feels very secure in the hotel.

Reviewed on Dec 27, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $549, price is now $329 per person
$329
per person
Mar 7 - Mar 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

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Sheridan Hotel Deals

Grand Bear Resort at Starved Rock

Grand Bear Resort at Starved Rock

3 out of 5
2643 IL-178 Utica IL
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Jan 5 to Jan 6
$127 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
7.2/10 Good! (1,002 reviews)
Room was very clean and the staff bent over backwards for our group of 14 .Already planning on making it an annual event at Grand Bear.

Reviewed on Dec 26, 2025

Grand Bear Resort at Starved Rock
Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

2 out of 5
1879 N 2703rd Rd Ottawa IL
$159 nightly
The price is $176 total per night from Jan 4 to Jan 5
$176 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.6/10 Exceptional! (97 reviews)
Everything was great. Staff more than helpful. Shay, Marita and Heather went above and beyond for any questions we had

Reviewed on Dec 14, 2025

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy
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
$75 nightly
The price is $82 total per night from Jan 4 to Jan 5
$82 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (804 reviews)
Room was spotless

Reviewed on Dec 26, 2025

Best Western Oswego Hotel
See all 373 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.

Find the Best Sheridan Vacation Packages

Sheridan Essential Information

Language
English
Currency
U.S dollars
Population
2,700
Max Temp Winter
30ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Sheridan vacation package cost?
Offering great value package deals from $235 on Expedia, you'll be thrilled with how little a vacation to Sheridan costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Sheridan?
February, August and November are the best times to search for cheap Sheridan vacation packages. Opting to travel in quieter periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Sheridan?
The ideal length for your Sheridan vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to visit all the top sights and explore some hidden spots along the way.
How to find the best Sheridan package deals?
Begin your search for a Sheridan package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Sheridan package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Sheridan getaway off to a flying start.
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 usually snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Sheridan vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Sheridan?
If you have your Sheridan vacation dates locked in, book as early as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for traveling on a whim.
Does Expedia offer Book Now, Pay Later Sheridan vacation packages?
Secure your dream escape to Sheridan with our Book Now, Pay Later vacations. No need to save up or wait for your next payday — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stay on budget and snap up bargains while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.