Title: Far North Side Luxury Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/553248635074842747/4c830a7f-a9f5-4e29-83f7-dc2e54b474ac.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far North Side Luxury Holidays ## Book a Luxury Hotel + Flight or Car together to unlock savings Photo by W. Ross Wells - ## 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 Far North Side Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago £825 per person 31 Mar - 5 Apr found 24 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) Great location, clean hotel Reviewed on 11 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 £850 per person 31 Mar - 5 Apr found 24 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back! Reviewed on 11 Jan 2026 ![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 Save 100% on your flight £1,233 per person 31 Mar - 5 Apr found 24 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room. Reviewed on 11 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 Save 100% on your flight £1,297 per person 31 Mar - 5 Apr found 2 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on 5 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 £871 per person 31 Mar - 5 Apr found 24 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 Jan 2026 Don't see what you're looking for? See all available trips from London to Far North Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-12/2026-02-19/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in Far North Side Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,135 per person 31 Mar - 5 Apr found 24 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Staff were impeccable.. greeted with small glass of champagne. Bed was comfortable, room was quiet. Would definitely stay here again.. Reviewed on 11 Jan 2026 ![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 Save 100% on your flight £1,233 per person 31 Mar - 5 Apr found 24 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room. Reviewed on 11 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 Save 100% on your flight £1,297 per person 31 Mar - 5 Apr found 2 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return. Reviewed on 5 Jan 2026 Don't see what you're looking for? See all available trips from London to Far North Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-12/2026-02-19/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in Far North Side Price found within the past 48 hours. Click for updated prices. ![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 £538 per person 25 Feb - 28 Feb 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 ![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 £582 per person 27 Feb - 2 Mar found 13 hours ago Return direct flight included Glasgow (GLA) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back! Reviewed on 11 Jan 2026 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare £630 per person 25 Feb - 28 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) Great stay fir early flights Reviewed on 8 Jan 2026 Don't see what you're looking for? See all available trips from London to Far North Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-12/2026-02-19/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in Far North Side Price found within the past 48 hours. Click for updated prices. ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago £885 per person 2 Apr - 6 Apr found 1 day ago Return flight included London (LON) to Chicago (ORD) 9/10 Wonderful! (380 reviews) I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay. Reviewed on 12 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 £1,225 per person 10 Mar - 14 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back! Reviewed on 11 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 £1,462 per person 10 Mar - 14 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Staff were impeccable.. greeted with small glass of champagne. Bed was comfortable, room was quiet. Would definitely stay here again.. Reviewed on 11 Jan 2026 Don't see what you're looking for? See all available trips from London to Far North Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-12/2026-02-19/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## All you need to know about luxury holidays in Far North Side #### What can I expect from a luxury Far North 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 Far North Side? Tick the all-inclusive and 5-star filters to find the crème de la crème of Far North 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 Far North 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 Far North Side starting at £538\. Prices and availability are subject to change. Additional terms may apply. #### Are there luxury spa holidays in Far North Side? For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Far North 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 Far North 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 Far North Side? You can wangle a top-notch luxury holiday in Far North 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 Far North 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 Far North Side with Expedia? Nobody does luxury quite like Expedia. With so many gorgeous properties in Far North 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 > - [Luxury Holidays in Cape Verde ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/32/Cape-Verde) > - [Luxury Holidays in Corfu ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/816/Corfu) > - [Luxury Holidays in Croatia ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/43/Croatia) > - [Luxury Holidays in Cyprus ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/45/Cyprus) > - [Luxury Holidays in Egypt ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/52/Egypt) > - [Luxury Holidays in Greece ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/67/Greece) > - [Luxury Holidays in Ibiza ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/1559/Ibiza-Town) > - [Luxury Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/86/Italy) > - [Luxury Holidays in Lanzarote ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/282/Lanzarote) > - [Luxury Holidays in the Maldives ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/109/Maldives) > - [Luxury Holidays in Mallorca ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/602317/Majorca-Island) > - [Luxury Holidays in Sicily ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/6048323/Sicily) > - [Luxury Holidays in Spain ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/166/Spain) > - [Luxury Holidays in Tenerife ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/6047194/Tenerife) > - [Luxury Holidays in Thailand ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/178/Thailand) > - [Luxury Holidays in Turkey ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/183/Turkey) > - [Luxury Holidays in the United Kingdom ](https://www.expedia.co.uk/lp/theme-holidays/luxury-holidays/190/United-Kingdom) ## More Holiday Ideas [Flights to Far North Side ](https://expedia.co.uk/Cheap-Flights-To-Far-North-Side.d553248635976475356.Travel-Guide-Flights)[ Far North Side Hotels ](https://expedia.co.uk/Far-North-Side-Hotels.d553248635976475356.Travel-Guide-Hotels)[ Far North Side Holiday Rentals ](https://expedia.co.uk/Far-North-Side-Holiday-Rentals.d553248635976475356.Travel-Guide-HolidayRentals)[ Far North Side Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Far-North-Side.d553248635976475356.Car-Hire-Guide)[ Far North Side Holidays ](https://expedia.co.uk/Far-North-Side.d553248635976475356.Holidays-City-Breaks) \* 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. ![](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