Title: Parkside Vacation Packages & Trips 2025 from $216 | Expedia.ca [Hotels in Parkside](https://expedia.ca/Parkside-Chicago-Hotels.0-n6132345-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Parkside Car Rentals](https://expedia.ca/Car-Rentals-In-Parkside.d6132345.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) # Parkside 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 Parkside Vacation Book a custom vacation package to Parkside and prepare to experience this city on your own terms. Think about spending some time in the neighborhood of Flossmoor, which is good for golfing and lots more. A trip to Parkside is an excellent opportunity to take in the sights. Be sure to stop by big-name attractions such as [Hollywood Casino Amphitheatre](https://www.expedia.ca/Hollywood-Casino-Amphitheatre-Tinley-Park.d6065119.Vacation-Attraction), [Odyssey Fun World](https://www.expedia.ca/Odyssey-Fun-World-Tinley-Park.d553248621532658609.Vacation-Attraction) and [George Dunne National Golf Club](https://www.expedia.ca/George-Dunne-National-Golf-Club-Parkside.d553248621532658611.Vacation-Attraction). Expedia can help you escape the everyday. Tailor your vacation to Parkside to suit your style of travel, whatever that may look like. ## Top Holiday Package Deals in Parkside Price found within the past 48 hours. Click for updated prices. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $656 per person Nov 17 - Nov 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-17/2025-11-20/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=z3t8Y2T71m0S8JmZE9iPjflS7zMKdH96uto9aQ4DwOlxXm-ae-MHhw3ehbo8tDlR) ![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 $1,492 per person Nov 7 - Nov 11 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) The staff was very friendly and accommodating. The rooms were clean and in excellent condition. The pool and spa were great features too. Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-07/2025-11-11/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=5en8rVcfXgv_kyiS2RCwb3445Xdt2kKz0ldFfzYxVFxmI0ElLWPN-7rPj56LIIvB) ![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 $1,200 per person Nov 5 - Nov 9 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice. Reviewed on Sep 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-09/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=9BfpBBk4iFRtCBx0_Y_KrSgdG2LZyzLLSj30Hyt4UTlElJ-R13sdv3Km0UaUMb2E) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,307 per person Dec 29 - Jan 2 found 20 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=dtx3vq16uPSd9QS67sCfUIxXFYQ20dOvXoGjP2JmmdFar8GrJyq5FQtmTtaDOnlC) ![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 $1,003 per person Nov 5 - Nov 9 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9/10 Wonderful! (352 reviews) Everything was wonder beside my shower head it was leaking bad Reviewed on Sep 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-09/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=9BfpBBk4iFRtCBx0_Y_Krdq8P3y_QENik07neBjK2fIKYnYHkiWybDgQrsyTE3hr) ## Where to stay in Parkside Find the best Parkside areas and neighborhoods for the activities you enjoy most. [Learn more about Parkside](https://expedia.ca/Chicago-Parkside.dx6132345) ![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago 5 out of top 10 points of interest in this area The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [Find hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(725 area reviews) Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park 5/5(20 area reviews) Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Parkside Hotel Deals ![Chicago Club Inn & Suites](https://images.trvl-media.com/lodging/1000000/10000/8500/8492/7c5f8bdd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chicago Club Inn & Suites 630 Pasquinelli Dr, Westmont, IL Fully refundableReserve now, pay when you stay CA $101 CA $112 total Oct 5 - Oct 6 includes taxes & fees 7/10 Good! (1,301 reviews) "Love it" Reviewed on Sep 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=8492&PinnedHotelID=8492&HadPinnedHotel=true®ionId=6132345) ![Red Roof Inn PLUS+ Chicago - Willowbrook](https://images.trvl-media.com/lodging/1000000/10000/4100/4013/dd62fe20_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn PLUS+ Chicago - Willowbrook 7535 Kingery Highway, Willowbrook, IL Fully refundableReserve now, pay when you stay CA $95 CA $107 total Oct 12 - Oct 13 includes taxes & fees 6.2/10 (1,018 reviews) "My go-to place in the area. Decor is somewhat dated and check-in is slow sometimes yet I come back because it’s a convenient location and the prices are reasonable. I prefer a 1st floor room and the staff will usually honor the request if they can." Reviewed on Sep 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F10%2F2025&endDate=13%2F10%2F2025&selected=4013&PinnedHotelID=4013&HadPinnedHotel=true®ionId=6132345) ![Hampton Inn by Hilton Chicago-Midway Airport](https://images.trvl-media.com/lodging/1000000/20000/12800/12800/8fbbd1df_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn by Hilton Chicago-Midway Airport 6540 S Cicero Ave, Chicago, IL Fully refundableReserve now, pay when you stay CA $188 CA $220 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (1,233 reviews) "Rooms were very clean, modern, and the staff was very friendly as well" Reviewed on Sep 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=12800&PinnedHotelID=12800&HadPinnedHotel=true®ionId=6132345) [See all 1,149 properties in Parkside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F10%2F2025&endDate=06%2F10%2F2025®ionId=6132345) 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 Parkside vacation package cost? > Customize your Parkside package from a low CA $656. Choose from any combination of flights, hotels and rental cars to craft the escape you've been dreaming about. Don't forget to add on a few experiences or activities! ### How do I get a cheap travel package to Parkside? > Booking a Parkside vacation package with Expedia is such a simple way to save. We have over 550 air carriers and 1,000,000 hotels all over the world. With such a broad range to choose from, you'll have no hassles putting together your dream vacation. ### Where should I stay in Parkside? > If you want to be in the thick of things, stay somewhere close to Hollywood Casino Amphitheatre. Many travelers book a hotel around this famous attraction. ### How far in advance should I book my Parkside vacation? > While prices change frequently, we generally advise booking your seats as soon as possible. Most international fares become available on Expedia up to a year in advance. If circumstances have left you booking last minute, you may still get lucky. Discount prices to Parkside sometimes occur in the weeks prior to departure. ### What does an Expedia Parkside travel package include? > Hotels, car rentals and flights — we bring you the very best bargains. All you have to do is select your favorite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an amazing Parkside trip. ### What should I know before booking a Parkside travel package? > Find deals that suit your budget with an Expedia package. Hotels, flights, rental cars — we have them all. You'll save precious cash just for bundling your bookings. Whether you're going on an adventure in the snow or kicking back on a warm beach, your dream vacation is only clicks away. ### Can I choose my airline with a Parkside Expedia vacation package? > Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to take your pick of available flights, hotels and activities that suit you. ### If I'm not able to travel, can I cancel my Parkside vacation package? > If your travel plans in Parkside have changed, it's good to know that it's possible to cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose fees. To find out more, check our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105). ### Discover the most popular places to visit in Parkside ![Wrigley Field featuring central business district, a city and a sporting event](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### Things to do ![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Architecture River Tour CA $67 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details) ![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Architecture Center River Cruise aboard First Lady CA $77 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Chicago](https://expedia.ca/things-to-do/search?rid=6132345) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.