Title: The Loop Holidays 2026 from £839 | Expedia.co.uk [The Loop Travel Guide](https://expedia.co.uk/Chicago-The-Loop.dx800024)[Hotels in The Loop](https://expedia.co.uk/The-Loop-Chicago-Hotels.0-n800024-0.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)[The Loop Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-The-Loop.d800024.Car-Hire-Guide) ![](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # The Loop Holidays from £839 ## 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 The Loop Holiday Lose yourself in the magic of this food-lovers neighbourhood with a The Loop holiday package. From its bars and pubs and history to its festivals, there's lots here for every traveller. Kick start your trip to The Loop with a visit 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). Expedia is here to help put your plans into action. Book your ideal The Loop holiday now. Price found within the past 48 hours. Click for updated prices. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston £839 per person 14 Mar - 21 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) Staff were very courteous and helpful. The room was pleasant. Reviewed on 31 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 £875 per person 22 Apr - 26 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Staff was extremely polite, rooms were clean. No issues at all Reviewed on 2 Feb 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 £1,116 per person 14 Mar - 21 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium. Reviewed on 31 Jan 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago £1,030 per person 14 Mar - 21 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,229 reviews) Strong marijuana smell and stingy on amenities in the room Reviewed on 2 Feb 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 £1,036 per person 17 Mar - 20 Mar found 7 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) The room was boring thought it would be cleaner updated for the price best part was the view Reviewed on 24 Jan 2026 ## Where to stay in The Loop Find the best The Loop areas and neighborhoods for the activities you enjoy most. [Learn more about The Loop](https://expedia.co.uk/Chicago-The-Loop.dx800024) ![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) ![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) ![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(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) ![Chicago featuring a city and modern architecture](https://images.trvl-media.com/place/6059328/2fb61786-4c0f-40e8-ae4e-a0fad3f9539a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park 5/5(5 area reviews) Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining. [Find hotels in Lincoln Park](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6059328) ## Top hotels in The Loop ![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 £78 3 Feb - 4 Feb includes taxes & fees 8/10 Very Good! (9,824 reviews) Good Reviewed on 30 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=03%2F02%2F2026&endDate=04%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=800024) ![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 £140 21 Feb - 22 Feb includes taxes & fees 8.4/10 Very Good! (2,592 reviews) The room was clean and the staff was very friendly. Reviewed on 28 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=800024) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Royal Sonesta Chicago Downtown 71 E Wacker Dr Chicago IL Fully refundableReserve now, pay when you stay £138 9 Feb - 10 Feb includes taxes & fees 9.2/10 Wonderful! (3,291 reviews) Everything was on point… we love the location Reviewed on 28 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=17543&PinnedHotelID=17543&HadPinnedHotel=true®ionId=800024) [See all 1,279 properties in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F02%2F2026&endDate=04%2F02%2F2026®ionId=800024) 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 ### Why should I book my The Loop holiday with Expedia? ### What are the top hotels for my holiday in The Loop? ### How do I get a cheap holiday to The Loop? ### What should I do on my The Loop holiday? ### What is the best area to stay in when on holiday in The Loop? ### Do I need a visa for my The Loop holiday? ### What should I wear on my The Loop holiday? ### What does an Expedia The Loop holiday include? ### Does Expedia offer Book Now, Pay Later The Loop holidays? > - [Pay monthly holidays](https://www.expedia.co.uk/lp/b/vacations/payment-plans): Realise your holiday dreams sooner with Klarna's convenient monthly instalment plans. If making small repayments each month works for you, pick this option at checkout. > - [No-deposit holidays](https://www.expedia.co.uk/lp/b/vacations/no-deposit-holidays): Hitting the "book now" button is easier with this payment option. With no upfront fee for your escape, you can Book Now, Pay Later and start working on your travel itinerary. ### Can I choose my airline with a The Loop Expedia holiday? ### Popular places to visit ![Millennium Park which includes autumn colours, modern architecture and street scenes](https://images.trvl-media.com/place/6069201/87d76a1e-e63f-48a2-8892-fb54ee86f8e1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park 4.5/5(147 reviews) A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape. [](https://expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction) ![Chicago Riverwalk featuring a river or creek, a bay or harbour and a city](https://images.trvl-media.com/place/553248621533116610/1742d80f-9a94-4104-8fda-70856c757147.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Riverwalk 4.5/5(29 reviews) Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped. [](https://expedia.co.uk/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Attraction) ![Art Institute of Chicago which includes art and interior views](https://images.trvl-media.com/place/6064021/978b5f18-f4d6-4af3-b8bd-e6b31b647559.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Art Institute of Chicago 4.5/5(66 reviews) Explore a massive collection of works celebrating different cultures and historical times, from ancient Egypt to modern installations. [](https://expedia.co.uk/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Attraction) ### 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=800024) ## Explore a world of travel with Expedia - 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[Things to do in Chicago ](https://www.expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) \* 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.