Title: The Loop Holidays 2026 from £540 | 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 £540 ## 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 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 £540 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (326 reviews) Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots. Reviewed on 18 Dec 2025 ![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 £900 per person 23 Jan - 28 Jan found 5 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,787 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![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 £837 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago £567 per person 23 Jan - 28 Jan found 5 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,059 reviews) Easy check in & out. Nice clean room, pool, & hotel. Hotel is old but that lends to a bit of nostalgia as maintenance & upkeep have keep the feeling of freshness alive. Reviewed on 19 Dec 2025 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £600 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Lobby is beautiful. My family and I enjoyed the hot tub. However, was disappointed in the cleanliness of our room. We arrived and one of the toilets looked as if it hadn’t been cleaned, there was visible urine on the toilet lid. We had called housekeeping and they showed up promptly to clean the toilet which was nice. Going onto the bathtub, there were short black hairs scattered in the tub when we first arrived, also indicating that it may not have been cleaned either. There was dust along the TV stand and all on top of the coffee maker and tray. On top of the cleanliness, we didn’t feel so safe. Upon checking into our room, the door handle didn’t have any problems. However coming back to our room at night after being out our door handle was very loose off the door, indicating that someone had tried to get in. We called and had someone come fix it. Overall, not sure if I will be returning to this hotel. I had booked this hotel because I have stayed here before and it was a great experience at that time but was kind of embarrassing to bring my family here. Reviewed on 19 Dec 2025 ## 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.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://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.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) ![Chicago which includes rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.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) ![Chicago featuring a city and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.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 ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL Fully refundableReserve now, pay when you stay £94 30 Dec - 31 Dec includes taxes & fees 9.2/10 Wonderful! (2,134 reviews) This hotel was great. In a perfect spot for walking the city and taking in all the sights. We had 3 of us in our group and we got the 1br with 2 queens beds and a pullout couch and it was perfect. The bar was fun and everyone we met in the staff were so friendly and helpful with suggestions on places ... Reviewed on 16 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=800024) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel Wacker at Michigan, Chicago 75 E Wacker Dr Chicago IL Fully refundableReserve now, pay when you stay £73 21 Dec - 22 Dec includes taxes & fees 8.6/10 Excellent! (1,992 reviews) Very clean and the staff was wonderful! Reviewed on 13 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=889753&PinnedHotelID=889753&HadPinnedHotel=true®ionId=800024) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL Fully refundableReserve now, pay when you stay £119 28 Dec - 29 Dec includes taxes & fees 8.4/10 Very Good! (2,142 reviews) Everything was great! Reviewed on 16 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=800024) [See all 1,248 properties in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F12%2F2025&endDate=21%2F12%2F2025®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 ![Chicago Riverwalk featuring a river or creek, a bay or harbour and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332109-Chicago-Riverwalk.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Riverwalk 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) ![Millennium Park which includes autumn colours, modern architecture and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26436-Millennium-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park 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) ![Willis Tower which includes a high-rise building, views and interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191767-Chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Willis Tower Visit the Skydeck and gaze down over the Chicago cityscape from a dazzling 1,353 feet above the sidewalk. [](https://expedia.co.uk/Willis-Tower-Downtown-Chicago.d6064069.Attraction) ### Things to do ![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 £30 per adult **94%** of travellers recommend [](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.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=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. 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