Title: Chicago Holidays 2026 from £511 | Expedia.co.uk [Chicago Travel Guide](https://expedia.co.uk/Chicago.dx178248)[Hotels in Chicago](https://expedia.co.uk/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Holiday Rentals in Chicago](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Chicago Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chicago.d178248.Car-Hire-Guide) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago Holidays from £511 ## Book a 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 Chicago Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston £511 per person 27 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) I would stay here again if I need to stay in Evanston again. Thanks Reviewed on 19 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 £684 per person 13 Apr - 17 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was top tier, from the room being spotless, to the professionalism of the staff, to the breakfast buffet. I will be returning to the Chicago location and also trying the resort in Mexico soon! Reviewed on 20 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 £617 per person 27 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Property was clean, welcoming, pet friendly Reviewed on 18 Jan 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago £889 per person 13 Apr - 17 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (3,392 reviews) The bellman helped get me a taxi and was especially nice. Reviewed on 19 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 £822 per person 13 Apr - 17 Apr found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Clean room and staff Reviewed on 20 Jan 2026 ## Where to stay in Chicago Find the best Chicago areas and neighborhoods for the activities you enjoy most. [Learn more about Chicago](https://expedia.co.uk/Chicago.dx178248) ![Downtown Chicago featuring a city](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Downtown Chicago 5 out of top 10 points of interest in this area The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [Find hotels in Downtown Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350699) ![Magnificent Mile - River North](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Magnificent Mile Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800025) ![The Loop - Downtown featuring a river or creek](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### The Loop 4.5/5(187 area reviews) Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=800024) ![River North showing railway items, street scenes and a city](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### River North Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. [Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=6350695) ![The dinosaur is ready for American football season.](https://images.trvl-media.com/place/829/7897d999-2146-461f-9e05-80d4a5ca217e.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### O'Hare 3.5/5(10 area reviews) Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago. [Find hotels in O'Hare](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods®ionId=553248635074842747) ### Things to do in Chicago Chicago is perfect for family, outdoor, and city-themed holidays, offering a vibrant mix of activities. Visitors can enjoy shopping areas, arena entertainment, and theatre performances. Key attractions include fascinating city tours, a Cubs game, outdoor activities, and live music events, ensuring a memorable experience in the Windy City. **Shopping** Experience shopping in Chicago at [Woodfield Mall](https://www.expedia.co.uk/Woodfield-Mall-Chicago.d6064089.Attraction), a vibrant centre with entertainment and family-friendly options. Visit [LEGOLAND® Discovery Center](https://www.expedia.co.uk/LEGOLAND-Discovery-Center-Chicago.d6169680.Attraction) for unique gifts and enjoy the [Arboretum of South Barrington](https://www.expedia.co.uk/Arboretum-Of-South-Barrington-Chicago.d6175734.Attraction), another lively mall offering a mix of shopping and entertainment for all ages. **Recreation** [Wrigley Field](https://www.expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction) offers a vibrant atmosphere for sports enthusiasts, where you can enjoy a game and soak in the lively energy. The [Chicago Theatre](https://www.expedia.co.uk/Chicago-Theatre-Downtown-Chicago.d6064049.Attraction) provides a cultural experience with its stunning performances and romantic ambiance, perfect for a family night out. [Cog Hill Golf & Country Club](https://www.expedia.co.uk/Cog-Hill-Golf-Country-Club-Chicago.d553248621532658527.Attraction) invites you to unwind amidst scenic outdoor beauty while enjoying a round of golf. **Adventure** [Galloping Ghost](https://www.expedia.co.uk/Galloping-Ghost-Chicago.d553248621532658619.Attraction) is an exhilarating arcade adventure zone in Chicago, offering a vibrant atmosphere filled with classic games for all ages. [Odyssey Fun World](https://www.expedia.co.uk/Odyssey-Fun-World-Chicago.d553248621532658520.Attraction) promises thrilling rides and arcade excitement, while [The People's Choice Family Fun Center](https://www.expedia.co.uk/The-Peoples-Choice-Family-Fun-Center-Chicago.d553248621532659203.Attraction) invites families to enjoy a delightful mix of games and activities. **Nightlife** Chicago's nightlife offers vibrant experiences with venues like Dave & Buster's, where you can enjoy drinks and fun entertainment vibes. For a romantic atmosphere, visit Kingston Mines or Blues on Halstead, both nightclubs that provide a lively mix of music and city allure. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in Chicago Chicago offers an ideal blend of family-friendly activities, outdoor adventures, and urban experiences. Visitors can explore urban parks, scenic beaches, and renowned universities, all while immersing themselves in the city's rich culture. For an unforgettable experience, be sure to spend time in downtown Chicago, where a wealth of attractions awaits, catering to diverse interests and providing lasting memories for all travellers. - **[Navy Pier: ](https://www.expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction)** Experience the vibrant atmosphere of Navy Pier, a lively jetty that offers stunning views of Lake Michigan. Enjoy a variety of entertainment options, including rides, restaurants, and shops, making it perfect for a fun day out with friends or family. - **[Michigan Avenue: ](https://www.expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction)** Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with luxurious shops, fine dining, and iconic architecture. Stroll along this vibrant thoroughfare to soak up the city's dynamic energy and discover unique boutiques. - **[Millennium Park: ](https://www.expedia.co.uk/Millennium-Park-Downtown-Chicago.d6069201.Attraction)** A must-visit urban park, Millennium Park features beautiful green spaces, public art installations like the famous Cloud Gate sculpture, and family-friendly events. It's an ideal spot for relaxation and enjoying outdoor activities in the heart of the city. ### Best time to go to Chicago The best time to visit Chicago is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 25.7°F (-3.5°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | February | 27.0°F (-2.8°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 37.0°F (2.8°C) | Light Rain | Mostly Cloudy | Average | Average | | April | 46.0°F (7.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | May | 57.0°F (13.9°C) | Light Rain | Mostly Sunny | Average | Average | | June | 67.3°F (19.6°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 73.4°F (23.0°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.0°F (22.8°C) | Light Rain | Mostly Sunny | Slightly High | Average | | September | 67.1°F (19.5°C) | Light Rain | Mostly Sunny | Average | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 42.3°F (5.7°C) | Light Rain | Mostly Sunny | Average | Average | | December | 33.1°F (0.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | ### Tips to save on your trip to Chicago - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Chicago. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Chicago Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | | Population | 2,720,500 | | Max Temp Winter | \-1.11ºC | | Max Temp Summer | 24ºC | | Top Sights | [Chicago Riverwalk](https://www.expedia.co.uk/Chicago-Riverwalk-Downtown-Chicago.d553248621533116610.Attraction), [Shedd Aquarium](https://www.expedia.co.uk/John-G-Shedd-Aquarium-Chicago.d6065141.Attraction) and [Art Institute of Chicago](https://www.expedia.co.uk/Art-Institute-Of-Chicago-Downtown-Chicago.d6064021.Attraction) | ## Top hotels in Chicago ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay £79 21 Jan - 22 Jan includes taxes & fees 8/10 Very Good! (9,789 reviews) Really interesting place, great price for the location too. Staff was very friendly. Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=21%2F01%2F2026&endDate=22%2F01%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=178248) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL Fully refundableReserve now, pay when you stay £136 1 Feb - 2 Feb includes taxes & fees 8.4/10 Very Good! (2,551 reviews) Did not have breakfast Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=01%2F02%2F2026&endDate=02%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=178248) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL Fully refundableReserve now, pay when you stay £93 9 Feb - 10 Feb includes taxes & fees 8.4/10 Very Good! (5,575 reviews) The staff were great! The room was pretty clean. The breakfast was amazing and, the kids loved to pool. The only issue we had was the elevator wait times. As that they were busy it made for long elevator wait times. Reviewed on 19 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=178248) [See all 5,654 properties in Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F01%2F2026&endDate=22%2F01%2F2026®ionId=178248) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](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 holidays](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) ![Holiday in Month](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) ### Popular places to visit ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue 4.5/5(14 reviews) You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.co.uk/Michigan-Avenue-Downtown-Chicago.d6156167.Attraction) ![Wrigley Field featuring a city, a sporting event and city views](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(40 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4/5(125 reviews) A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.co.uk/Navy-Pier-Downtown-Chicago.d6069215.Attraction) ### What to do in Chicago ![Chicago: Navy Pier Centennial Wheel Regular & Express Ticket](https://mediaim.expedia.com/localexpert/4851853/9464687e-f5ac-4a15-9285-f6e26537484c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: Navy Pier Centennial Wheel Ticket £18 per adult **88%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details) ![Chicago C3® : Save on admission to your choice of 3 top attractactions](https://mediaim.expedia.com/localexpert/46362450/da44d619-18fc-4969-97e2-f7b8d0da99b5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago C3® by CityPASS® £79 per adult **90%** of travellers recommend [](https://expedia.co.uk/things-to-do/chicago-c3-by-citypass.a46362450.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket £25 per adult **96%** of travellers recommend [](https://expedia.co.uk/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=178248) ## Explore a world of travel with Expedia - 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[Things to do in Central Chicago ](https://www.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. 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