Title: Northwest Side Cheap 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 Cheap Holidays ## Book a Cheap 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 + Cheap hotel deals in Northwest Side Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago £1,253 per person 2 May - 7 May found 10 hours ago Return direct flight included Birmingham (BHX) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Beautiful room. Property upgraded to 2-bedroom. Facilities are great with huge gym. Great stay in Chicago. Reviewed on 14 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 £1,505 per person 1 Jun - 6 Jun found 9 hours ago Return direct flight included Birmingham (BHX) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The breakfast was incredibly delicious. The hotel in general is a 10 out of 10. Reviewed on 20 Mar 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago £1,494 per person 2 May - 7 May found 10 hours ago Return direct flight included Birmingham (BHX) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great location, views, & amenities. Reviewed on 20 Mar 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago £1,478 per person 2 May - 7 May found 11 hours ago Return direct flight included Birmingham (BHX) to Chicago (ORD) 9.4/10 Exceptional! (3,646 reviews) Nice room, fun rooftop bar, late to check in, room wasn’t ready but it was St Patty’s day so lots of revelers. Reviewed on 18 Mar 2026 ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago £1,543 per person 2 May - 7 May found 11 hours ago Return direct flight included Birmingham (BHX) to Chicago (ORD) 9.2/10 Wonderful! (2,091 reviews) Staff were very nice Reviewed on 18 Mar 2026 Don't see what you're looking for? See all available trips from Birmingham to Northwest Side [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-04-20/2026-04-27/?FromAirport=BHX&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Cheap 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 Save 100% on your flight £1,822 per person 15 May - 20 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good. Reviewed on 16 Mar 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago £2,101 per person 15 May - 20 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,007 reviews) Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again. Reviewed on 1 Mar 2026 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/e294b3a4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago £2,446 per person 15 May - 20 May found 1 day ago Return flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,010 reviews) Excellent in every way! Reviewed on 17 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/2026-04-20/2026-04-27/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Cheap holidays 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 £1,034 per person 15 May - 18 May found 1 day ago Return flight included London (LHR) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again. Reviewed on 19 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 £1,111 per person 15 May - 18 May found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The breakfast was incredibly delicious. The hotel in general is a 10 out of 10. Reviewed on 20 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 £1,118 per person 15 May - 18 May found 1 day ago Return flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (3,314 reviews) The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.! Reviewed on 17 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/2026-04-20/2026-04-27/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Cheap 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 £770 per person 22 Apr - 26 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The breakfast was incredibly delicious. The hotel in general is a 10 out of 10. Reviewed on 20 Mar 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago £782 per person 22 Apr - 26 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,646 reviews) Nice room, fun rooftop bar, late to check in, room wasn’t ready but it was St Patty’s day so lots of revelers. Reviewed on 18 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 £1,214 per person 22 Apr - 26 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special! Reviewed on 16 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/2026-04-20/2026-04-27/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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) ## 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