Title: Central Chicago Romantic 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 Romantic Holidays ## Book a Romantic 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 + Romantic hotel deals in Central Chicago 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 £1,166 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Clean room and amenities Reviewed on 8 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 Save 100% on your flight £1,612 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) 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 ![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 £1,181 per person 1 Apr - 8 Apr found 1 day ago Return direct flight included Belfast (BFS) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was great just the doors for entering and exiting the building were a hassle to open and push through. Not accessible easily the revolving door was the only way to get in and out and you had to manually push it. It was a heavy door and hard to push with all your stuff. Reviewed on 29 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 £1,281 per person 3 Mar - 9 Mar found 21 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 Jan 2026 ![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 £1,222 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 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/2026-02-28/2026-03-07/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Central Chicago Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago £1,278 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Staff was wonderful. Reviewed on 25 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 Save 100% on your flight £1,612 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) 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 ![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 £1,281 per person 3 Mar - 9 Mar found 21 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better. Reviewed on 26 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/2026-02-28/2026-03-07/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic 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 £1,073 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was great just the doors for entering and exiting the building were a hassle to open and push through. Not accessible easily the revolving door was the only way to get in and out and you had to manually push it. It was a heavy door and hard to push with all your stuff. Reviewed on 29 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 Save 100% on your flight £1,612 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) 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 ![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 £1,222 per person 15 Mar - 19 Mar found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 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/2026-02-28/2026-03-07/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Central Chicago holiday #### How can I find the best Central Chicago vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to Central Chicago. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino. #### Can I book cheap Central Chicago romantic holidays for two? Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Central Chicago that start from £1,073\. Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a Central Chicago romantic getaway? The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure. #### What should I look for in a luxury romantic holiday to Central Chicago? Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service. #### Can I book a romantic hot-tub holiday in Central Chicago? What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter. #### How can I find romantic holidays for couples in Central Chicago that are all inclusive? Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available. #### Can I book a romantic trip to Central Chicago with free cancellation and/or flexible dates? Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print. #### Why should I book my Central Chicago romantic holiday with Expedia? At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing. ## 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 Romantic Holiday Destinations > - [Romantic Holidays in Barcelona ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179992/Barcelona) > - [Romantic Holidays in Cornwall ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/10558/Cornwall) > - [Romantic Holidays in Cyprus ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/45/Cyprus) > - [Romantic Holidays in France ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/59/France) > - [Romantic Holidays in Greece ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/67/Greece) > - [Romantic Holidays in Ibiza ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/1559/Ibiza-Town) > - [Romantic Holidays in Italy ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/86/Italy) > - [Romantic Holidays in Morocco ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/122/Morocco) > - [Romantic Holidays in Paris ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179898/Paris) > - [Romantic Holidays in Portugal ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/147/Portugal) > - [Romantic Holidays in Rome ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179899/Rome) > - [Romantic Holidays in Santorini ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/177970/Santorini) > - [Romantic Holidays in Scotland ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/11219/Scotland) > - [Romantic Holidays in Thailand ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/178/Thailand) > - [Romantic Holidays in the Maldives ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/109/Maldives) > - [Romantic Holidays in the United Kingdom ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/190/United-Kingdom) > - [Romantic Holidays in the USA ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/201/United-States-Of-America) > - [Romantic Holidays in Turkey ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/183/Turkey) > - [Romantic Holidays in Venice ](https://www.expedia.co.uk/lp/theme-holidays/romantic-holidays/179981/Venice) ## More Holiday Ideas [Flights to Central Chicago ](https://expedia.co.uk/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights)[ Central Chicago Hotels ](https://expedia.co.uk/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels)[ Central Chicago Holiday Rentals ](https://expedia.co.uk/Central-Chicago-Holiday-Rentals.d553248635976475413.Travel-Guide-HolidayRentals)[ Central Chicago Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Central-Chicago.d553248635976475413.Car-Hire-Guide)[ Central Chicago Holidays ](https://expedia.co.uk/Central-Chicago.d553248635976475413.Holidays-City-Breaks)[ Things to do in Central Chicago ](https://expedia.co.uk/Things-To-Do-In-Central-Chicago.d553248635976475413.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. ![](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