Title: Northwest Side Romantic Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Northwest Side Romantic Holidays ## Book a Romantic 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 + Romantic hotel deals in Northwest 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 £680 per person 5 Mar - 9 Mar found 13 hours 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 ![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 £1,234 per person 2 Apr - 7 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on 20 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 £867 per person 5 Mar - 9 Mar found 13 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 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 £983 per person 31 Mar - 4 Apr found 17 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on 22 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 £1,060 per person 31 Mar - 4 Apr found 17 hours 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 Northwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic 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/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £867 per person 5 Mar - 9 Mar found 13 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 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 £1,234 per person 2 Apr - 7 Apr found 1 day ago Return direct flight included Manchester (MAN) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) First time there. Staff was helpful and they provided excellent memorable service Reviewed on 20 Jan 2026 ![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 £926 per person 5 Mar - 9 Mar found 13 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,001 reviews) Yes didn’t know you get free breakfast Reviewed on 4 Jan 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/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic 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 £726 per person 2 Mar - 5 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on 22 Jan 2026 ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago £895 per person 2 Mar - 5 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often. Reviewed on 20 Jan 2026 ![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 £861 per person 2 Mar - 5 Mar found 1 day ago Return flight included London (LON) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Great staff that paid attention quickly to concerns. Reviewed on 19 Jan 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/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Northwest 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 £680 per person 5 Mar - 9 Mar found 13 hours 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 ![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 £867 per person 5 Mar - 9 Mar found 13 hours ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Exceptional service, great location, beautiful hotel Reviewed on 20 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 £983 per person 31 Mar - 4 Apr found 17 hours ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) No parking available, the hotel was nice, room etc. but breakfast was overly crowded, cafeteria style. They say breakfast is free with stay but then I was charged $85\. When I asked what the charge was for they said for breakfast, room service etc. plus parking was an additional $150, not on site so not too pleased with the overall experience. Staff was very nice though. Reviewed on 22 Jan 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/2026-02-22/2026-03-01/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## How to find a romantic Northwest Side holiday #### How can I find the best Northwest Side vacation packages for couples? Use our easy-to-use holiday search tools to plan your most-romantic getaway to Northwest Side. 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 Northwest Side 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 Northwest Side that start from £680\. Prices and availability are subject to change. Additional terms may apply. #### What should I think about when booking a Northwest Side 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 Northwest Side? 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 Northwest Side? 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 Northwest Side 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 Northwest Side 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 Northwest Side 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 Northwest Side ](https://expedia.co.uk/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[ Northwest Side Hotels ](https://expedia.co.uk/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[ Northwest Side Holiday Rentals ](https://expedia.co.uk/Northwest-Side-Holiday-Rentals.d553248635976475367.Travel-Guide-HolidayRentals)[ Northwest Side Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Northwest-Side.d553248635976475367.Car-Hire-Guide)[ Northwest Side Holidays ](https://expedia.co.uk/Northwest-Side.d553248635976475367.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