Title: Near West Side Vacation Packages | Holiday Packages & Trips 2026/2027 from Expedia.ca [Near West Side Travel Guide](https://expedia.ca/Chicago-Near-West-Side.dx6132434)[Hotels in Near West Side](https://expedia.ca/Near-West-Side-Chicago-Hotels.0-n6132434-0.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)[Near West Side Car Rentals](https://expedia.ca/Car-Rentals-In-Near-West-Side.d6132434.Car-Rental-Guide) ![](https://images.trvl-media.com/place/829/1a47d60f-edf5-4e44-b25c-6a3708851864.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Near West Side Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by throwingsofas - ## 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 ## Where to stay in Near West Side Find the best Near West Side areas and neighborhoods for the activities you enjoy most. [Learn more about Near West Side](https://expedia.ca/Chicago-Near-West-Side.dx6132434) ![Downtown Chicago showing a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.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://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.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://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.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) ![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.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) ![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### O'Hare 3.5/5(38 area reviews) Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates. [Find hotel + flight trips in O'Hare](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=O%27Hare&DestID=553248635074842747&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ## Near West Side Hotel Deals ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Crowne Plaza Chicago West Loop by IHG 25 South Halsted Street Chicago IL Fully refundableReserve now, pay when you stay CA $139 CA $163 total Feb 16 - Feb 17 includes taxes & fees 8.8/10 Excellent! (1,944 reviews) Staff nice and the hotel was beautiful Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=1293276&PinnedHotelID=1293276&HadPinnedHotel=true®ionId=6132434) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Emily Hotel 311 North Morgan Street Chicago IL Fully refundableReserve now, pay when you stay CA $208 CA $244 total Mar 1 - Mar 2 includes taxes & fees 9/10 Wonderful! (1,301 reviews) Quiet room for Chicago and amazing neighborhood. And one block away for self parking. Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=19381112&PinnedHotelID=19381112&HadPinnedHotel=true®ionId=6132434) ![Hyatt House Chicago West Loop](https://images.trvl-media.com/lodging/36000000/35840000/35834300/35834237/d1cc0289_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt House Chicago West Loop 105 N MAY STREET Chicago IL Fully refundableReserve now, pay when you stay CA $195 CA $229 total Feb 16 - Feb 17 includes taxes & fees 8.8/10 Excellent! (1,176 reviews) Clean, great breakfast, helpful staff. A very good experience Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=35834237&PinnedHotelID=35834237&HadPinnedHotel=true®ionId=6132434) [See all 4,994 properties in Near West Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026®ionId=6132434) 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 Near West Side vacation package cost? ### How do I get a cheap travel package to Near West Side? ### Where should I stay in Near West Side? ### What are the top hotels in Near West Side? ### How far in advance should I book my Near West Side vacation? ### What does an Expedia Near West Side travel package include? ### What should I know before booking a Near West Side travel package? ### Can I choose my airline with a Near West Side Expedia vacation package? ### If I'm not able to travel, can I cancel my Near West Side vacation package? ### Discover the most popular places to visit in Near West Side ![Chicago_UnitedCenter_6064077_01](https://images.trvl-media.com/place/6064077/45e0cfe3-9e5f-4653-8161-042a957b09fc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### United Center Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices. [](https://expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction) ### Things to do ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $46 per adult **96%** 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=6132434) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.