Title: Northwest Side Luxury Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/553248635976475367/bfa3a438-7753-4d4b-b110-6e23898993ba.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Northwest Side Luxury Holidays ## Book a Luxury 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 ## Top flight + Luxury hotel deals in Northwest Side 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 £1,421 per person 3 Jun - 10 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value Reviewed on 24 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 £1,578 per person 3 Jun - 10 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property. Reviewed on 26 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 £1,568 per person 3 Jun - 10 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (3,314 reviews) Great stay! Would stay again! Reviewed on 26 Mar 2026 ![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 £1,923 per person 3 Jun - 10 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,019 reviews) Amazing location, super friendly staff, tiny room. Reviewed on 26 Mar 2026 ![The Godfrey Hotel Chicago](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/4bc08adf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Godfrey Hotel Chicago Downtown Chicago £1,851 per person 3 Jun - 10 Jun found 1 day ago Return flight included London (LON) to Chicago (ORD) 8.8/10 Excellent! (2,096 reviews) Refused to park my challenger for valet Reviewed on 25 Mar 2026 Don't see what you're looking for? See all available trips from London to Northwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Northwest Side 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 £1,090 per person 2 May - 4 May found 4 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Perfect room size for 2+1\. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit. We will be back in near future for surr! Reviewed on 24 Mar 2026 Don't see what you're looking for? See all available trips from London to Northwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Northwest Side 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 £950 per person 10 May - 13 May found 5 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property. Reviewed on 26 Mar 2026 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £1,156 per person 10 May - 13 May found 5 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. Reviewed on 23 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 £1,399 per person 10 May - 13 May found 5 hours ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Perfect room size for 2+1\. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit. We will be back in near future for surr! Reviewed on 24 Mar 2026 Don't see what you're looking for? See all available trips from London to Northwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-26/2026-05-03/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury holidays in Northwest Side #### What can I expect from a luxury Northwest Side 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 Northwest Side? Tick the all-inclusive and 5-star filters to find the crème de la crème of Northwest Side 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 Northwest Side? 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 Northwest Side starting at £950\. Prices and availability are subject to change. Additional terms may apply. #### Are there luxury spa holidays in Northwest Side? For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Northwest Side 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 Northwest Side? 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 Northwest Side? You can wangle a top-notch luxury holiday in Northwest Side 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 Northwest Side 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 Northwest Side with Expedia? Nobody does luxury quite like Expedia. With so many gorgeous properties in Northwest Side 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