Title: Sheridan Vacation Packages & Trips 2026 from CA $521 | 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.

![Holiday Inn Express & Suites Prospect Heights by IHG](https://images.trvl-media.com/lodging/1000000/900000/898100/898065/3d1fbdd0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Holiday Inn Express & Suites Prospect Heights by IHG

CA $521

per person

Feb 13 - Feb 20

found 11 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

9/10 Wonderful! (876 reviews)

This place was so good

Reviewed on Dec 21, 2025

![DoubleTree by Hilton Chicago Schaumburg](https://images.trvl-media.com/lodging/1000000/20000/17500/17443/e6f3488b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### DoubleTree by Hilton Chicago Schaumburg

CA $606

per person

Feb 13 - Feb 20

found 11 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

7.2/10 Good! (1,003 reviews)

The room was clean. Staff and bar was really nice.

Reviewed on Dec 18, 2025

![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Chicago O'Hare Airport

O'Hare

CA $1,240

per person

Feb 13 - Feb 20

found 11 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

8.2/10 Very Good! (2,158 reviews)

Staff was excellent, roim was nice

Reviewed on Dec 30, 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 $1,205

per person

Feb 4 - Feb 8

found 4 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

It was like a Ritz Carlton like experience without the Ritz Carlton price tag.

Reviewed on Dec 31, 2025

![DoubleTree by Hilton Chicago - North Shore Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15600/15560/8a058213_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### DoubleTree by Hilton Chicago - North Shore Conference Center

CA $669

per person

Feb 13 - Feb 20

found 11 hours ago

Roundtrip flight included

Calgary (YYC) to Chicago (ORD)

8.8/10 Excellent! (1,002 reviews)

Decent and plenty. Good service.

Reviewed on Dec 31, 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

Fully refundableReserve now, pay when you stay

CA $150

CA $172 total

Jan 12 - Jan 13

includes taxes & 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

[](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=1500830&PinnedHotelID=1500830&HadPinnedHotel=true&regionId=6085097)

### 

Postcard Cabins Starved Rock, Outdoor Collection by Marriott Bonvoy

1879 N 2703rd Rd Ottawa IL

CA $139

CA $215 total

Jan 20 - Jan 21

includes taxes & 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

[](https://expedia.ca/Hotel-Search?startDate=20%2F01%2F2026&endDate=21%2F01%2F2026&selected=110272793&PinnedHotelID=110272793&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 $103

CA $112 total

Jan 11 - Jan 12

includes taxes & fees

8.6/10 Excellent! (804 reviews)

Room was spotless

Reviewed on Dec 26, 2025

[](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=424318&PinnedHotelID=424318&HadPinnedHotel=true&regionId=6085097)

[See all 373 properties in Sheridan](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F01%2F2026&endDate=03%2F01%2F2026&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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