Title: Glenwood Vacation Packages & Trips 2026 from CA $1,073 | Expedia.ca [Hotels in Glenwood](https://expedia.ca/Glenwood-Hotels.d3000434169.Travel-Guide-Hotels)[Vacation Rentals in Glenwood](https://expedia.ca/Glenwood-Vacation-Rentals.d3000434169.Travel-Guide-VacationRentals)[Glenwood Car Rentals](https://expedia.ca/Car-Rentals-In-Glenwood.d3000434169.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) # Glenwood 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 #### Your Glenwood Vacation Lock in a Glenwood vacation package and get ready to experience this amazing city the easy way. Think about staying in the neighborhood of South Deering, which is good for golfing and nature. Fill up your itinerary with tours of [Coyote Run Golf Course](https://www.expedia.ca/Coyote-Run-Golf-Course-Flossmoor.d6186281.Vacation-Attraction), [River Oaks Center](https://www.expedia.ca/River-Oaks-Center-Chicago.d6250782.Vacation-Attraction) and [Ravisloe Country Club](https://www.expedia.ca/Ravisloe-Country-Club-Chicago.d6186265.Vacation-Attraction), some of the things you really should see during a trip to Glenwood. Stop daydreaming and start doing. Explore the multitude of options on Expedia today and finally put your Glenwood vacation plans into motion! ## Top Glenwood Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Hilton Garden Inn Chicago Central Loop](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102882/w3837h2621x0y0-5bb1f388_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Central Loop Downtown Chicago CA $1,073 per person Jun 26 - Jun 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,300 reviews) Everything was really nice! Reviewed on Mar 29, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,684 per person May 26 - May 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Amazing experience will be back soon Reviewed on Mar 29, 2026 ![Sports Illustrated Resorts Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/d70b1c1f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sports Illustrated Resorts Chicago Downtown Chicago CA $1,583 per person May 26 - May 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,414 reviews) Check in was quick and easy, room was clean and spacious Reviewed on Mar 9, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $1,367 per person Jun 5 - Jun 8 found 1 hour ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (441 reviews) The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing Reviewed on Mar 27, 2026 ![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/69dc07eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Viceroy Chicago Downtown Chicago CA $1,546 per person May 26 - May 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,187 reviews) Very nice place on the Gold Coast! Reviewed on Mar 23, 2026 ## Ready to book your vacation to Glenwood? Choose your dates ## Glenwood Hotel Deals ![DoubleTree by Hilton Chicago - Alsip](https://images.trvl-media.com/lodging/1000000/30000/25600/25507/fcb66f28_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Chicago - Alsip 5000 W 127th St Alsip IL Fully refundableReserve now, pay when you stay CA $159 CA $180 total Apr 5 - Apr 6 includes taxes & fees 8.4/10 Very Good! (1,015 reviews) Overall experience was good Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=25507&PinnedHotelID=25507&HadPinnedHotel=true®ionId=3000434169) ![Hilton Chicago/Oak Lawn](https://images.trvl-media.com/lodging/1000000/20000/17700/17618/0e1ccba8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Oak Lawn 9333 S Cicero Ave Oak Lawn IL Fully refundableReserve now, pay when you stay CA $164 CA $189 total Apr 7 - Apr 8 includes taxes & fees 8.4/10 Very Good! (1,259 reviews) Staff was very nice, room was clean, stay was comfortable Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=17618&PinnedHotelID=17618&HadPinnedHotel=true®ionId=3000434169) ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Chicago – Midway Airport S by IHG 7353 S Cicero Avenue Chicago IL Fully refundable CA $124 CA $159 total Apr 5 - Apr 6 includes taxes & fees 8.2/10 Very Good! (1,000 reviews) But the parking 23$ omg Reviewed on Mar 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=2190&PinnedHotelID=2190&HadPinnedHotel=true®ionId=3000434169) [See all 951 properties in Glenwood](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=02%2F04%2F2026&endDate=03%2F04%2F2026®ionId=3000434169) 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) ## 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. ![](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