Title: Sheridan Vacation Packages & Trips 2026 from CA $641 | Expedia.ca

[Sheridan Travel Guide](https://expedia.ca/Sheridan.dx6085097)[Hotels in Sheridan](https://expedia.ca/Sheridan-Hotels.d6085097.Travel-Guide-Hotels)[Vacation Rentals in Sheridan](https://expedia.ca/Sheridan-Vacation-Rentals.d6085097.Travel-Guide-VacationRentals)[Sheridan Car Rentals](https://expedia.ca/Car-Rentals-In-Sheridan.d6085097.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Sheridan Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Plan, book, and manage your trip all in one place

## Top Sheridan Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $641

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Elegant interiors and excellent breakfast menu

Reviewed on Dec 22, 2025

![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Waldorf Astoria Chicago

Downtown Chicago

CA $2,223

per person

Mar 1 - Mar 7

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Chicago (ORD)

9.4/10 Exceptional! (1,000 reviews)

Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago – Old Town

Downtown Chicago

CA $891

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

CA $1,153

per person

Mar 14 - Mar 17

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Loved it here and would stay again! Everything was perfect!

Reviewed on Dec 21, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $1,152

per person

Mar 1 - Mar 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Service and clean room - paying attention to the details

Reviewed on Dec 22, 2025

## Ready to book your vacation to Sheridan?

Choose your dates

## Sheridan Hotel Deals

![Grand Bear Resort at Starved Rock](https://images.trvl-media.com/lodging/2000000/1510000/1500900/1500830/c6b13292_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Grand Bear Resort at Starved Rock

2643 IL-178 Utica IL

CA $156

CA $179 total

Jan 5 - Jan 6, 2026

includes taxes & fees

7.2/10 Good! (1,002 reviews)

We went for the water park, which was the perfect size for our young kids, but everything else was fine too and service was attentive.

Reviewed on Dec 20, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=1500830&PinnedHotelID=1500830&HadPinnedHotel=true&regionId=6085097)

![Best Western Oswego Hotel](https://images.trvl-media.com/lodging/1000000/430000/424400/424318/7b695b40_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Best Western Oswego Hotel

2055 Wiesbrook Dr Oswego IL

Fully refundableReserve now, pay when you stay

CA $104

CA $113 total

Dec 28 - Dec 29

includes taxes & fees

8.6/10 Excellent! (797 reviews)

Overall everything was great

Reviewed on Dec 17, 2025

[](https://expedia.ca/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=424318&PinnedHotelID=424318&HadPinnedHotel=true&regionId=6085097)

![Holiday Inn Aurora North - Naperville by IHG](https://images.trvl-media.com/lodging/2000000/1730000/1723200/1723200/9e01bcf6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Holiday Inn Aurora North - Naperville by IHG

2424 Sullivan Rd Aurora IL

Fully refundable

CA $131

CA $143 total

Jan 4 - Jan 5, 2026

includes taxes & fees

7.8/10 Good! (833 reviews)

clean room shower door was sticky

Reviewed on Dec 17, 2025

[](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=1723200&PinnedHotelID=1723200&HadPinnedHotel=true&regionId=6085097)

[See all 373 properties in Sheridan](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F12%2F2025&endDate=24%2F12%2F2025&regionId=6085097)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

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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.

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