Title: Central Chicago Luxury Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/bd91735e-0c7e-4d0c-8152-a9d6fd38ff30.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Central Chicago Luxury Holidays ## Book a Luxury Hotel + Flight or Car together to unlock savings Photo by Phil Ostroff - ## 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 ## Top flight + Luxury hotel deals in Central Chicago Price found within the past 48 hours. Click for updated prices. ![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 £1,063 per person 20 May - 27 May found 16 hours ago Return flight included London (LON) to Chicago (ORD) 8.2/10 Very Good! (2,573 reviews) the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well. The location is excellent and i would go back. Reviewed on 4 Mar 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 Save 100% on your flight £1,301 per person 20 May - 27 May found 16 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Loved my stay her staff was very hospitable and met all our needs. The breakfast buffet was the best I have ever been to. Reviewed on 9 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £1,342 per person 20 May - 27 May found 16 hours ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 ![Sports Illustrated Resorts Chicago](https://images.trvl-media.com/lodging/10000000/9120000/9119600/9119528/bc30a848_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sports Illustrated Resorts Chicago Downtown Chicago £1,237 per person 20 May - 27 May found 16 hours ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,407 reviews) We chose this hotel for my husband’s birthday weekend. The room was spacious clean and trendy. The bed was so comfortable. The happy hour was excellent and the game room and bar on the second floor was fabulous. The customer service was phenomenal. They surprised my husband with a goody bag for his birthday which was the icing on the cake. The hotel is currently undergoing renovations but it was still a great stay. Reviewed on 3 Mar 2026 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago £1,231 per person 20 May - 27 May found 16 hours ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (3,285 reviews) Great stay. Staff was slightly inattentive at times with requests for things to room. Reviewed on 9 Mar 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Central Chicago Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,177 per person 13 Apr - 16 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,839 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on 3 Mar 2026 ![Nobu Hotel Chicago](https://images.trvl-media.com/lodging/37000000/36480000/36475600/36475533/ccd16d9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Nobu Hotel Chicago Downtown Chicago £2,311 per person 20 May - 27 May found 16 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (795 reviews) This was an amazing stay. The staff was incredibly helpful and welcoming. In a gray lo Reviewed on 9 Mar 2026 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago £1,297 per person 27 Apr - 30 Apr found 1 day ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.2/10 Wonderful! (1,001 reviews) Great location, service, and gym Reviewed on 24 Jan 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Central Chicago 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 £743 per person 27 Apr - 30 Apr found 1 day ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Loved my stay her staff was very hospitable and met all our needs. The breakfast buffet was the best I have ever been to. Reviewed on 9 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £918 per person 27 Apr - 30 Apr found 1 day ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,177 per person 13 Apr - 16 Apr found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,839 reviews) Above the beyond. My back went out. Had wheelchair Asap took me uop and helprd mre get into bed. Reviewed on 3 Mar 2026 Don't see what you're looking for? See all available trips from Glasgow to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=GLA&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Central Chicago Price found within the past 48 hours. Click for updated prices. ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago £848 per person 23 Apr - 27 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,993 reviews) Very clean, small but beautiful updated rooms. Great location. Would stay again. Discounted parking close by. Reviewed on 9 Mar 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 £876 per person 23 Apr - 27 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Loved my stay her staff was very hospitable and met all our needs. The breakfast buffet was the best I have ever been to. Reviewed on 9 Mar 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/d235a6b6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £882 per person 23 Apr - 27 Apr found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,310 reviews) Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again. Reviewed on 7 Mar 2026 Don't see what you're looking for? See all available trips from London to Central Chicago [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-09/2026-04-16/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury holidays in Central Chicago #### What can I expect from a luxury Central Chicago holiday? Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes. #### How can I find all-inclusive luxury holidays in Central Chicago? Tick the all-inclusive and 5-star filters to find the crème de la crème of Central Chicago holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end. #### Can I book a cheap luxury holiday to Central Chicago? A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Central Chicago starting at £743\. Prices and availability are subject to change. Additional terms may apply. #### Are there luxury spa holidays in Central Chicago? For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Central Chicago spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh. #### What should I look for when booking a luxury family holiday in Central Chicago? Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore. #### Can I book luxury last-minute holidays to Central Chicago? You can wangle a top-notch luxury holiday in Central Chicago for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better! #### Can I book a luxury holiday in Central Chicago with free cancellation and/or flexible dates? If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions. #### Why should I book my luxury travel to Central Chicago with Expedia? Nobody does luxury quite like Expedia. With so many gorgeous properties in Central Chicago to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book. ## More holidays 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 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 holiday packages](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) ![](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) ### Top Luxury Holiday Destinations > - 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Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app