Title: Stephenson County Vacations & Trips 2026 from CA $548 | Expedia.ca [Stephenson County Hotels](https://expedia.ca/Destinations-In-Stephenson-County.d553248635976430579.Hotel-Destinations)[Vacation Rentals in Stephenson County](https://expedia.ca/Destinations-In-Stephenson-County.d553248635976430579.Vacation-Rental-Destinations)[Stephenson County Car Rentals](https://expedia.ca/Destinations-In-Stephenson-County.d553248635976430579.Car-Rental-Destinations) ![](https://images.trvl-media.com/place/7257/44bd852b-c0c5-4e1c-b348-5b12973508ef.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Stephenson County Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Tina Techsavvymum - ## 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 Stephenson County Vacation Deals Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $548 per person Feb 23 - Feb 27 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on Dec 8, 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 $988 per person Feb 23 - Feb 27 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 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 $628 per person Feb 23 - Feb 27 found 5 hours 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 ![Radisson Blu Aqua Hotel Chicago](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Radisson Blu Aqua Hotel Chicago Downtown Chicago CA $725 per person Jan 31 - Feb 6 found 19 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (1,761 reviews) Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks! Reviewed on Dec 14, 2025 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $802 per person Feb 23 - Feb 27 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable! Reviewed on Dec 13, 2025 ## Stephenson County Hotel Deals ![Country Inn & Suites by Radisson, Freeport, IL](https://images.trvl-media.com/lodging/1000000/30000/28000/27974/9cdfac50_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Country Inn & Suites by Radisson, Freeport, IL 1710 South Dirck Drive Freeport IL Fully refundable CA $146 CA $162 total Jan 7 - Jan 8, 2026 includes taxes & fees 8.8/10 Excellent! (847 reviews) Friendly, helpful staff, delicious coffee, Cookies in the lobby, a great full breakfast with lots of warm and easy-to-grab options, microwave in the room. We’ve stayed twice and enjoyed it b Reviewed on Dec 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=27974&PinnedHotelID=27974&HadPinnedHotel=true®ionId=553248635976430579) ![Baymont by Wyndham Freeport](https://images.trvl-media.com/lodging/1000000/570000/565200/565130/89a0a36f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Freeport 1060 Riverside Dr Freeport IL Fully refundableReserve now, pay when you stay CA $111 CA $123 total Dec 22 - Dec 23 includes taxes & fees 7.8/10 Good! (709 reviews) Stayed for a night, i must say the stay is nice. The place needs updating. Not today but in the future. Reviewed on Nov 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=565130&PinnedHotelID=565130&HadPinnedHotel=true®ionId=553248635976430579) ![Hampton Inn Freeport](https://images.trvl-media.com/lodging/2000000/1640000/1632400/1632362/3a80a350_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn Freeport 109 S Galena Ave Freeport IL Fully refundableReserve now, pay when you stay CA $137 CA $152 total Jan 4 - Jan 5, 2026 includes taxes & fees 8.6/10 Excellent! (447 reviews) The room was clean, the staff was nice and the breakfast bar was very good Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=1632362&PinnedHotelID=1632362&HadPinnedHotel=true®ionId=553248635976430579) [See all 256 properties in Stephenson County](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=16%2F12%2F2025&endDate=17%2F12%2F2025®ionId=553248635976430579) 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) ## Frequently asked questions ### How much does a Stephenson County vacation package cost? ### How do I get a cheap travel package to Stephenson County? ### How far in advance should I book my Stephenson County vacation? ### What does an Expedia Stephenson County travel package include? ### What should I know before booking a Stephenson County travel package? ### Can I choose my airline with a Stephenson County Expedia vacation package? ### If I'm not able to travel, can I cancel my Stephenson County vacation package? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app