Title: Near South Side Holidays 2026 from £615 | Expedia.co.uk [Near South Side Travel Guide](https://expedia.co.uk/Chicago-Near-South-Side.dx6132399)[Hotels in Near South Side](https://expedia.co.uk/Near-South-Side-Chicago-Hotels.0-n6132399-0.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 South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Near-South-Side.d6132399.Car-Hire-Guide) ![](https://images.trvl-media.com/place/6132399/bed0102f-0e70-4cb1-8baa-b00fec33aaca.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Near South Side Holidays from £615 ## Book a Hotel + Flight or Car together to unlock savings - ## 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 South Side Holiday Book a holiday package to Near South Side and get set to immerse yourself in its history, walking and culture. However you want to spend your time in this lakeside neighbourhood, there are plenty of opportunities for relaxation and fun. Your trip to Near South Side wouldn't be complete without stopping by leading attractions nearby 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). Don't just dream it — turn it into reality! Secure your ideal Near South Side holiday with Expedia and enjoy travelling your way. Price found within the past 48 hours. Click for updated prices. ![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 £615 per person 5 Mar - 9 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often. Reviewed on 20 Jan 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 £617 per person 5 Mar - 9 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Great hotel and expect Reviewed on 22 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 £867 per person 5 Mar - 9 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room and the staff were wonderful! Reviewed on 22 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 £1,566 per person 5 Apr - 10 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on 20 Jan 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £680 per person 5 Mar - 9 Mar found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 Jan 2026 ## Where to stay in Near South Side Find the best Near South Side areas and neighborhoods for the activities you enjoy most. [Learn more about Near South Side](https://expedia.co.uk/Chicago-Near-South-Side.dx6132399) ![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) ![The dinosaur is ready for American football season.](https://images.trvl-media.com/place/829/7897d999-2146-461f-9e05-80d4a5ca217e.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### O'Hare 3.5/5(10 area reviews) Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago. [Find hotels in O'Hare](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635074842747) ## Top hotels in Near South Side ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay £79 24 Jan - 25 Jan includes taxes & fees 8/10 Very Good! (9,789 reviews) Really interesting place, great price for the location too. Staff was very friendly. Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132399) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL Fully refundableReserve now, pay when you stay £136 1 Feb - 2 Feb includes taxes & fees 8.4/10 Very Good! (2,551 reviews) Did not have breakfast Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=6132399) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL Fully refundableReserve now, pay when you stay £93 5 Feb - 6 Feb includes taxes & fees 8.4/10 Very Good! (5,575 reviews) The staff were great! The room was pretty clean. The breakfast was amazing and, the kids loved to pool. The only issue we had was the elevator wait times. As that they were busy it made for long elevator wait times. Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=05%2F02%2F2026&endDate=06%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132399) [See all 4,769 properties in Near South Side](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F01%2F2026&endDate=24%2F01%2F2026®ionId=6132399) 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 South Side travel package cost? ### If I'm not able to travel, can I cancel my Near South Side travel package? ### How do I get a cheap travel package to Near South Side? ### Does Expedia offer Book Now, Pay Later Near South Side holidays? > - Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's monthly instalment plans. If paying bite-sized amounts each month works for you, pick this option during the checkout process. > - Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna. > - Low deposit holidays: If paying a small percentage of your getaway (rather than the 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 South Side? ### What are the top hotels in Near South Side? ### How far in advance should I book my Near South Side holiday? ### What does an Expedia Near South Side travel package include? ### What should I know before booking a Near South Side travel package? ### Can I choose my airline with a Near South Side Expedia travel package? ### Things to do ![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 **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.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 £25 per adult **96%** of travellers recommend [](https://expedia.co.uk/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=6132399) \* 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.