Title: Glenwood Vacation Packages & Trips 2026 from CA $843 | 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. ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $843 per person May 17 - May 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) Everything was perfect Reviewed on Mar 26, 2026 ![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 $1,020 per person Jun 3 - Jun 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Hotel is in a good central location near many of the main attractions. Room was spacious and clean. Nice bar downstairs, there is also a rooftop bar, but that is only open in after Easter in summer. Buffet breakfast is included and that makes it very good value. Hotel also has a gym/ Not too many amenities in the room though. Reviewed on Apr 2, 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 $1,017 per person Jun 3 - Jun 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) This hotel provides the basics no amenities you have to pay extra for breakfast and any amenities you would like. Reviewed on Apr 3, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,244 per person Jun 9 - Jun 12 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Garage area very dark and unsafe Reviewed on Mar 31, 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $1,143 per person Jun 3 - Jun 6 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. 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 $164 CA $186 total Apr 22 - Apr 23 includes taxes & fees 8.4/10 Very Good! (1,004 reviews) I love the hotel. No complaints about the staff. However I wasn’t able to relax because of the constant traffic on the floor. Overall a pretty rocky stay. Reviewed on Apr 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%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 $170 CA $195 total Apr 22 - Apr 23 includes taxes & fees 8.4/10 Very Good! (1,265 reviews) Staff was very nice, room was clean, stay was comfortable Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F04%2F2026&endDate=23%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 $135 CA $172 total Apr 5 - Apr 6 includes taxes & fees 8.2/10 Very Good! (1,002 reviews) Super nice, friendly staff. They made my stay a delight. The room was clean and comfortable! Lots of shopping and restaurants nearby. Reviewed on Apr 1, 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=04%2F04%2F2026&endDate=05%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