Sheridan Vacations from $283

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The Latest Sheridan vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $479, price is now $283 per person
$283
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The staff was very responsive, the view nice, the location was great.

Reviewed on Dec 5, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $770, price is now $438 per person
$438
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,048, price is now $606 per person
$606
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate

Reviewed on Dec 2, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $543, price is now $327 per person
$327
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $486, price is now $295 per person
$295
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Wonderful ! Clean ! Staff helpful! Great location near everything beautiful views !

Reviewed on Dec 5, 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
$106 nightly
The price is $117 total per night from Dec 8 to Dec 9
$117 total
Dec 8 - Dec 9
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
Very courteous staff, clean rooms, easy access to various activities both at Grand bear and in the surrounding area. Also surprisingly quiet considering the amount of families that were there. Better Sound insulation than expected.

Reviewed on Dec 2, 2025

Grand Bear Resort at Starved Rock
Holiday Inn Aurora North - Naperville by IHG

Holiday Inn Aurora North - Naperville by IHG

3 out of 5
2424 Sullivan Rd Aurora IL
Fully refundable
$91 nightly
The price is $99 total per night from Dec 21 to Dec 22
$99 total
Dec 21 - Dec 22
Total with taxes and fees
7.8/10 Good! (823 reviews)
Clean, friendly, comfy

Reviewed on Dec 1, 2025

Holiday Inn Aurora North - Naperville by IHG
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 Dec 14 to Dec 15
$82 total
Dec 14 - Dec 15
Total with taxes and fees
8.6/10 Excellent! (782 reviews)
Staff

Reviewed on Dec 1, 2025

Best Western Oswego Hotel
See all 376 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 $283 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.