Title: West Side Vacation Packages 2026 from $232 | Expedia.com [West Side Travel Guide](https://expedia.com/West-Side.dx553248635976475400)[Hotels in West Side](https://expedia.com/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[Vacation Rentals in West Side](https://expedia.com/West-Side-Vacation-Rentals.d553248635976475400.Travel-Guide-VacationRentals)[Flights to West Side](https://expedia.com/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[Things to do in West Side](https://expedia.com/Things-To-Do-In-West-Side.d553248635976475400.Travel-Guide-Activities)[Car Rentals in West Side](https://expedia.com/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide) ![](https://images.trvl-media.com/place/829/ad657303-bbed-4f45-9ba5-b7c23d3e76f3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West Side Vacations from $232 ## Book a Hotel + Flight or Car together to unlock savings Photo by throwingsofas - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## The Latest West Side vacation packages Price found within the past 48 hours. Click for updated prices. ![Holiday Inn Chicago - Schaumburg by IHG](https://images.trvl-media.com/lodging/13000000/12080000/12078100/12078090/c8bab089_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Chicago - Schaumburg by IHG Save 100% on your flight $232 per person Apr 10 - Apr 13 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (999 reviews) Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy. Reviewed on Jan 11, 2026 ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago Save 100% on your flight $472 per person Apr 18 - Apr 23 found 13 hours ago Roundtrip flight included Los Angeles (LAX) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 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 Save 100% on your flight $339 per person Mar 9 - Mar 12 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Excellent in every way Reviewed on Feb 6, 2026 ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago Save 100% on your flight $614 per person Apr 30 - May 3 found 17 hours ago Roundtrip flight included Dallas (DAL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Bottle of waters were not stocked in the refrigerator. Reviewed on Jan 6, 2026 ![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 Save 100% on your flight $615 per person Mar 9 - Mar 12 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Lovely room. Excellent staff. Reviewed on Feb 3, 2026 Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-06/2026-03-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Where to stay in West Side Find the best West Side areas and neighborhoods for the activities you enjoy most. [Learn more about West Side](https://expedia.com/West-Side.dx553248635976475400) ![Blue Hour evening cityscape in West Loop neighborhood. Long exposure, nightscape architecture. Main street in Chicago, streets in Illinois.](https://images.trvl-media.com/place/553248634029130868/e4d15962-627f-4352-9768-bd3b891abed4.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Loop 1 out of top 10 points of interest in this area Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center. [Find hotel + flight trips in West Loop](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Loop&DestID=553248634029130868&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago Skyline from the west side with the train](https://images.trvl-media.com/place/6132439/f88c6ed3-b251-4bec-bb60-b3e94382f91f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Town 2 out of top 10 points of interest in this area 4.5/5(107 area reviews) Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city. [Find hotel + flight trips in West Town](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Town&DestID=6132439&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![A view of the Chicago skyline from the rooftop of the Ace Hotel in the West Loop.](https://images.trvl-media.com/place/829/1a47d60f-edf5-4e44-b25c-6a3708851864.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near West Side 4 out of top 10 points of interest in this area 4.5/5(740 area reviews) Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by Credit Union 1 Arena or United Center while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town. [Find hotel + flight trips in Near West Side](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Near%20West%20Side&DestID=6132434&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lawndale 1 out of top 10 points of interest in this area When in Lawndale and the surrounding area, you'll want to check out sights like Garfield Park Conservatory or United Center and hop on the metro to see more the city at Central Park Station (Pink Line) or Pulaski Station (Pink Line). [Find hotel + flight trips in Lawndale](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lawndale&DestID=553248635976384042&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Wicker Park Historic District, a residential neighbourhood, Chicago, Illinois, USA](https://images.trvl-media.com/place/6227639/a89281f3-851c-4c74-8025-215bb2cb4b7b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wicker Park Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area. [Find hotel + flight trips in Wicker Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Wicker%20Park&DestID=6227639&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in 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 4.5/5(701 reviews) 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.com/United-Center-Near-West-Side.d6064077.Vacation-Attraction) ![Tri Taylor](https://images.trvl-media.com/place/6064083/510a09ea-94c5-44a3-9ca1-0c370cf8aba5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Illinois Chicago 4/5(832 reviews) Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area. [](https://expedia.com/University-Of-Illinois-Chicago-Near-West-Side.d6064083.Vacation-Attraction) ![Path with Yellow Flowers at the Humboldt Park Lagoon](https://images.trvl-media.com/place/507386/55ced313-3fc9-4929-87bb-442fd1e5875b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Humboldt Park 3.5/5(2 reviews) Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed art scene in this vibrant area. [](https://expedia.com/Humboldt-Park-West-Town.d507386.Vacation-Attraction) ### What to do in West Side ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket $25 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.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 $38 per adult **98%** of travellers recommend [](https://expedia.com/things-to-do/flyover-in-chicago.a50023979.activity-details) ![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 $41 per adult **94%** of travellers recommend [](https://expedia.com/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in West Side](https://expedia.com/things-to-do/search?rid=553248635976475400) ## 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 $103 nightly $120 total Feb 16 - Feb 17 Total with taxes and fees 8.8/10 Excellent! (1,944 reviews) Staff nice and the hotel was beautiful Reviewed on Feb 5, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=1293276&PinnedHotelID=1293276&HadPinnedHotel=true®ionId=553248635976475400) ![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 $179 nightly $210 total Feb 15 - Feb 16 Total with taxes and 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.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=19381112&PinnedHotelID=19381112&HadPinnedHotel=true®ionId=553248635976475400) ![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 $144 nightly $169 total Feb 15 - Feb 16 Total with taxes and fees 8.8/10 Excellent! (1,178 reviews) Stellar stay as usual. Clean. Amazing staff. And we LOVE that there’s a restaurant attached now. Just awesome. Reviewed on Feb 4, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%2F2026&selected=35834237&PinnedHotelID=35834237&HadPinnedHotel=true®ionId=553248635976475400) [See all 895 properties in West Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=553248635976475400) 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. ## Find the Best West Side Vacation Packages ## West Side Essential Information | Language | English | | --------------- | -------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | ## More vacations you might like ![](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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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