Title: Near West Side Holidays 2026 from £827 | Expedia.co.uk [Hotels in Near West Side](https://expedia.co.uk/Near-West-Side-Chicago-Hotels.0-n6132434-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Near West Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Near-West-Side.d6132434.Car-Hire-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 Holidays from £827 ## Book a Hotel + Flight or Car together to unlock savings Photo by throwingsofas - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected ### Your Near West Side Holiday Take all the stress out of planning your next adventure with a Near West Side holiday package. Take in the sounds and sights of this appealing neighbourhood and experience all it has to offer. Kick start your trip to Near West Side by heading to nearby attractions such as [Millennium Park](https://www.expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction), [Willis Tower](https://www.expedia.co.uk/Willis-Tower-Downtown-Chicago.d6064069.Attraction) and [Art Institute of Chicago](https://www.expedia.co.uk/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Attraction). Whatever your dream Near West Side holiday may look like, you can turn it into reality with Expedia. 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 £827 per person 31 Mar - 5 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back! Reviewed on 11 Jan 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago Save 100% on your flight £1,209 per person 31 Mar - 5 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room. Reviewed on 11 Jan 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 £959 per person 4 Mar - 9 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing Reviewed on 13 Jan 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago Save 100% on your flight £1,297 per person 31 Mar - 5 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on 5 Jan 2026 ![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 £876 per person 31 Mar - 5 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) Had an amazing stay. Just note, you need to ask for the room cleaning service, and its not for everyday. Overall really loved the place and hope to come back! Reviewed on 10 Jan 2026 ## 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.co.uk/Chicago-Near-West-Side.dx6132434) ![Downtown Chicago featuring 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 hotels in Downtown Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350699) ![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 Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800025) ![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(187 area reviews) Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800024) ![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 Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. [Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350695) ![Beautiful fireworks](https://images.trvl-media.com/place/829/1a8abde0-c15d-4b25-9c4c-74d2678f7428.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Theatre District While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line). [Find hotels in Theatre District](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=651190586167894016) ## Top hotels in Near West Side ![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 £79 25 Jan - 26 Jan includes taxes & fees 8.8/10 Excellent! (1,866 reviews) Room was great and room and hotel smelled fresh. Sounds funny but some hotels have areas that stink. Water pressure was excellent and service was exceptional! Reviewed on 12 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=1293276&PinnedHotelID=1293276&HadPinnedHotel=true®ionId=6132434) ![Nobu Hotel Chicago](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/486e1134_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Nobu Hotel Chicago 155 N. Peoria Street Chicago IL £260 28 Jan - 29 Jan includes taxes & fees 9.2/10 Wonderful! (775 reviews) Great room & excellent customer service! Reviewed on 6 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F01%2F2026&endDate=29%2F01%2F2026&selected=36475533&PinnedHotelID=36475533&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 £126 22 Jan - 23 Jan includes taxes & fees 8.8/10 Excellent! (1,159 reviews) Clean hotel. Beautiful bar and very friendly employees! Reviewed on 10 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F01%2F2026&endDate=23%2F01%2F2026&selected=35834237&PinnedHotelID=35834237&HadPinnedHotel=true®ionId=6132434) [See all 4,876 properties in Near West Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F01%2F2026&endDate=15%2F01%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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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 Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## Frequently asked questions ### How much does a Near West Side travel package cost? ### If I'm not able to travel, can I cancel my Near West Side travel package? ### How do I get a cheap travel package to Near West Side? ### Does Expedia offer Book Now, Pay Later Near West Side holidays? > - Pay monthly holidays: Klarna has manageable monthly payment plans that work for all types of budgets, so you can book that well-earned holiday sooner. > - Pay in instalments holidays: If you want to pay off your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna. > - Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna. ### 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 holiday? ### 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 travel package? ### Popular places to visit ![United Center](https://mediaim.expedia.com/destination/2/46d6593c111467d37042f3aa65728da7.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.co.uk/United-Center-Near-West-Side.d6064077.Attraction) ### Things to do ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission £33 per adult **100%** of travellers recommend [](https://expedia.co.uk/things-to-do/skydeck-willis-tower-admission.a1342523.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 £18 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details) ![Chicago C3® : Save on admission to your choice of 3 top attractactions](https://mediaim.expedia.com/localexpert/46362450/da44d619-18fc-4969-97e2-f7b8d0da99b5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago C3® by CityPASS® £79 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.activity-details) [See all activities in Chicago](https://expedia.co.uk/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. Flight-inclusive packages are ATOL protected.