Sheridan Vacations from $185

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The Latest Sheridan vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $342, price is now $185 per person
$185
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $944, price is now $457 per person
$457
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
great staff...loved our stay.

Reviewed on Nov 22, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,292, price is now $680 per person
$680
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.

Reviewed on Nov 25, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,029, price is now $544 per person
$544
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I thoroughly enjoyed my time at Pendry Chicago. I stayed in a tower king room. I originally was going to stay in a suite but the normal king room was very spacious for one person. The valet service was pretty quick and the valets were all very nice. The front desk clerk was extremely helpful and professional. I loved staying right on Michigan Ave and within walking distance to so many things. I read some reviews saying safety was a concern but I didn’t experience any safety issues. They lock the doors on Michigan Ave after a certain point to keep the flow of traffic thru a better monitored entrance. I also took an evening(beginning around 9:30pm) stroll around Millennium Park, down to Buckingham fountain and back up Michigan Ave to the river and the surroundings blocks around the hotel. At no point did I feel unsafe and would highly recommend this hotel to anyone coming to Chicago. The location is fantastic, the employees are amazing and the rooms are comfy. What more could you ask for?

Reviewed on Nov 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $611, price is now $332 per person
$332
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Clean, quiet and comfortable room, courteous staff. We received a $25k food credit through Expedia and got exceptional pastries and coffee at the adjacent cafe.

Reviewed on Nov 22, 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
$112 nightly
The price is $124 total per night from Nov 30 to Dec 1
$124 total
Nov 30 - Dec 1
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
Carissa was amazing and very helpful. She was the front desk manager in the evening. And was very helpful and kind. Unfortunately, the front desk morning staff was not as friendly and helpful.

Reviewed on Nov 20, 2025

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
$71 nightly
The price is $78 total per night from Dec 10 to Dec 11
$78 total
Dec 10 - Dec 11
Total with taxes and fees
8.6/10 Excellent! (771 reviews)
Very clean room and hotel, friendly staff, had all amenities needed.

Reviewed on Nov 10, 2025

Best Western Oswego Hotel
Holiday Inn Express & Suites Yorkville by IHG

Holiday Inn Express & Suites Yorkville by IHG

2.5 out of 5
577 E KENDALL DRIVE Yorkville IL
Fully refundable
$77 nightly
The price is $84 total per night from Dec 7 to Dec 8
$84 total
Dec 7 - Dec 8
Total with taxes and fees
8.2/10 Very Good! (613 reviews)
Good stay

Reviewed on Nov 15, 2025

Holiday Inn Express & Suites Yorkville by IHG
See all 375 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 $185 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.

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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.