Title: West Side Vacation Packages 2026 from $493 | 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 $493 ## Book a Hotel + Flight or Car together to unlock savings Photo by throwingsofas ## The Latest West Side vacation packages Price found within the past 48 hours. Click for updated prices. ![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 $493 per person Jun 1 - Jun 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The staff was very kind and check in/out was quick. Great breakfast buffet! Reviewed on Mar 24, 2026 ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago $545 per person Jun 3 - Jun 7 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value Reviewed on Mar 24, 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 Save 100% on your flight $704 per person Jun 18 - Jun 21 just found Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9/10 Wonderful! (441 reviews) Staff was really nice Reviewed on Mar 24, 2026 ![Hilton Garden Inn Chicago Downtown South Loop](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Downtown South Loop Downtown Chicago Save 100% on your flight $663 per person Jun 17 - Jun 20 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.8/10 Excellent! (1,894 reviews) Great location, underwhelming stay overall. Nice rooms, crowded amenities, snack area rarely stocked, staff seemed uninvested in our experience. Reviewed on Mar 24, 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 $541 per person Apr 26 - Apr 29 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 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/2026-04-25/2026-05-02/?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 Old St Patrick’s Church 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(751 area reviews) Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena 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) ![606 Trail Wicker Park](https://images.trvl-media.com/place/6227639/4f7be21f-2085-45e6-ab70-172236c98d9c.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) ![Congrats to the Chicago Blackhawks on winning their third Stanley cup in 6 years, you are a dynasty. I was lucky enough to see a first round playoff game in Chicago, loved the city and loved the arena , great atmosphere, wish my team was as good as the hawks ](https://images.trvl-media.com/place/829/6bee6eb6-4f1b-46da-984f-9f3146c0a1f1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### United Center If you're spending time in United Center, check out sights like United Center or Michael Jordan Statue and hop on the metro to see more the city at Illinois Medical District Station or Western Station (Forest Park Branch). [Find hotel + flight trips in United Center](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=United%20Center&DestID=643562035333914624&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in West Side ![Aerial view of the iconic John Hancock Center and shimmering skyscrapers meeting the tranquil blue of Lake Michigan's shoreline, Chicago, Illinois, United States.](https://images.trvl-media.com/place/6064077/4d148b7d-946b-4968-91c3-37e9729a12ca.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### United Center 4.5/5(717 reviews) Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums. [](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(837 reviews) Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theater scene 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 acclaimed theater scene and entertainment choices in this vibrant area. [](https://expedia.com/Humboldt-Park-West-Town.d507386.Vacation-Attraction) ### What to do in West Side ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck $27 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Bulls Basketball Game at United Center $66 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details) ![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) [See all activities in West Side](https://expedia.com/things-to-do/search?rid=553248635976475400) ## West Side Hotel Deals ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Emily Hotel 311 North Morgan Street Chicago IL Fully refundableReserve now, pay when you stay $237 nightly $278 total Mar 29 - Mar 30 Total with taxes and fees 9.2/10 Wonderful! (1,328 reviews) Great hotel and close to our dinner reservation. Reviewed on Mar 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=19381112&PinnedHotelID=19381112&HadPinnedHotel=true®ionId=553248635976475400) ![Crowne Plaza Chicago West Loop by IHG](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Crowne Plaza Chicago West Loop by IHG 25 South Halsted Street Chicago IL Fully refundable $125 nightly $147 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (2,024 reviews) First time in Chicago after a long time, will definitely come back to this hotel when I come back Reviewed on Mar 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=1293276&PinnedHotelID=1293276&HadPinnedHotel=true®ionId=553248635976475400) ![Holiday Inn & Suites Chicago - Downtown by IHG](https://images.trvl-media.com/lodging/1000000/210000/201300/201274/9b3b5e62_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn & Suites Chicago - Downtown by IHG 506 West Harrison Street Chicago IL Fully refundable $128 nightly $151 total Mar 29 - Mar 30 Total with taxes and fees 8.6/10 Excellent! (1,001 reviews) Good lactations. Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=201274&PinnedHotelID=201274&HadPinnedHotel=true®ionId=553248635976475400) [See all 774 properties in West Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F26%2F2026&endDate=3%2F27%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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Savings not available on all packages.