Title: Visit Sleepy Hollow: 2026 Sleepy Hollow, Chicago Travel Guide | Expedia.com [Hotels in Sleepy Hollow](https://expedia.com/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.com/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.com/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Car Rentals in Sleepy Hollow](https://expedia.com/Car-Rentals-In-Sleepy-Hollow.d6132427.Car-Rental-Guide)[Sleepy Hollow Vacations](https://expedia.com/Sleepy-Hollow.d6132427.Destination-Travel-Guides) # Sleepy Hollow, IL ## Chicago ## Visit Sleepy Hollow Things to do Hotels Where to stay [Chicago Travel Guide](https://expedia.com/Chicago.dx178248) --- ### Popular places to visit ![Wrigley Field](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(2,149 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.com/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![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(336 reviews) You can enjoy some retail therapy 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.com/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes 4.5/5(461 reviews) After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. [](https://expedia.com/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction) ![McCormick Place](https://images.trvl-media.com/place/6069191/6dd1da52-961b-4d36-a030-f105009f678b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### McCormick Place 4.5/5(1,830 reviews) Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges. [](https://expedia.com/McCormick-Place-Near-South-Side.d6069191.Vacation-Attraction) ![Millennium Park](https://images.trvl-media.com/place/6069201/87d76a1e-e63f-48a2-8892-fb54ee86f8e1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Millennium Park 4.5/5(7,305 reviews) A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape. [](https://expedia.com/Millennium-Park-Downtown-Chicago.d6069201.Vacation-Attraction) ![Navy Pier](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4.5/5(4,923 reviews) A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.com/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### Things to do ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck $27 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Bulls Basketball Game at United Center $66 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details) ![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 $25 per adult **88%** of travellers recommend [](https://expedia.com/things-to-do/chicago-navy-pier-centennial-wheel-ticket.a4851853.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago $38 per adult **98%** of travellers recommend [](https://expedia.com/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour $41 per adult **94%** of travellers recommend [](https://expedia.com/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![cruise ship sailing past navy pier in chicago](https://mediaim.expedia.com/localexpert/173241/21d8d1a0-e61c-4298-ab2f-118c1794b450.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Chicago: Lake Michigan Premier Dinner Cruise $137 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.activity-details) [See all activities in Chicago](https://expedia.com/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) --- ## Sleepy Hollow Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL $115 nightly $135 total Apr 5 - Apr 6 Total with taxes and fees Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ... 8/10 Very Good! (10,001 reviews) Bar wasn’t open as much as would like - room was nice location good. Can’t fault it lovely location in Chicago. Reviewed on Mar 28, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132427) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL $122 nightly $143 total Apr 5 - Apr 6 Total with taxes and fees Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ... 9/10 Wonderful! (4,004 reviews) Clean and well kept overall. Great Australian restaurant in the lobby. Reviewed on Mar 28, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132427) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL $130 nightly $152 total Apr 12 - Apr 13 Total with taxes and fees Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ... 8.6/10 Excellent! (5,790 reviews) Great spot in the shopping district. Good breakfast and nice to have the snacks and drinks for the happy hour time. Reviewed on Mar 28, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132427) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL $146 nightly $172 total Apr 5 - Apr 6 Total with taxes and fees Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ... 9.4/10 Exceptional! (3,658 reviews) Breakfast was bland, cups, plates, forks not clean. Housekeeping didn’t clean rooms property, wasn’t made aware roof top wasn’t open if that was the case I would have never booked. Staff poorly communicated late checkout guidelines. Reviewed on Mar 28, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=6132427) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL $227 nightly $267 total Apr 25 - Apr 26 Total with taxes and fees Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ... 8.4/10 Very Good! (2,238 reviews) Everything was clean and the staff was very friendly and helpful! Reviewed on Mar 25, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F25%2F2026&endDate=4%2F26%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=6132427) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Wade 644 N Lake Shore Dr Chicago IL $144 nightly $169 total Apr 27 - Apr 28 Total with taxes and fees Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and ... 8.4/10 Very Good! (1,758 reviews) No water view Reviewed on Mar 27, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F27%2F2026&endDate=4%2F28%2F2026&selected=1346&PinnedHotelID=1346&HadPinnedHotel=true®ionId=6132427) [See all 4,828 properties in Sleepy Hollow](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F29%2F2026&endDate=3%2F30%2F2026®ionId=6132427) 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. ## Check Sleepy Hollow hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132427&startDate=2026-03-28&endDate=2026-03-29)[Mar 28 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132427&startDate=2026-03-28&endDate=2026-03-29) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132427&startDate=2026-03-29&endDate=2026-03-30)[Mar 29 - Mar 30](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132427&startDate=2026-03-29&endDate=2026-03-30) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132427&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132427&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) --- ### Other neighborhoods around Sleepy Hollow ![Near West Side](https://images.trvl-media.com/place/829/1a47d60f-edf5-4e44-b25c-6a3708851864.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near West Side 4.5/5(751 area reviews) Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town. [](https://expedia.com/Chicago-Near-West-Side.dx6132434) ![Blue Hour evening cityscape in West Loop neighborhood. Long exposure, nightscape architecture. Main street in Chicago, streets in Illinois.](https://images.trvl-media.com/place/553248634029130868/e4d15962-627f-4352-9768-bd3b891abed4.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Loop Consider a visit to Old St Patrick’s Church and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center. [](https://expedia.com/Chicago-West-Loop.dx553248634029130868) ![South Loop](https://images.trvl-media.com/place/6130108/f1bd0360-1400-4c1c-882e-1779972b657f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### South Loop 4.5/5(615 area reviews) Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Soldier Field and Lake Michigan are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city. [](https://expedia.com/Chicago-South-Loop.dx6130108) ![Chicago Skyline from the west side with the train](https://images.trvl-media.com/place/6132439/f88c6ed3-b251-4bec-bb60-b3e94382f91f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### West Town 4.5/5(107 area reviews) Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city. [](https://expedia.com/Chicago-West-Town.dx6132439) ![Chicago_NearSouthSide_6132399_02](https://images.trvl-media.com/place/6132399/bed0102f-0e70-4cb1-8baa-b00fec33aaca.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Near South Side Travelers choose Near South Side for its abundant dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field. [](https://expedia.com/Chicago-Near-South-Side.dx6132399) ![606 Trail Wicker Park](https://images.trvl-media.com/place/6227639/4f7be21f-2085-45e6-ab70-172236c98d9c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wicker Park Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area. [](https://expedia.com/Chicago-Wicker-Park.dx6227639) [See our Where To Stay guide](https://expedia.com/Chicago.dx178248.Where-To-Stay?rfrr=TG.LP.Dest.Neigh.Neighborhoods) --- --- - [Stays](?pwaLob=wizard-hotel-pwa-v2) - [Packages](?pwaLob=wizard-package-pwa) - [Flights](?pwaLob=wizard-flight-pwa) - [Things to do](?pwaLob=wizard-lx-pwa) - [Cruises](?pwaLob=wizard-cruise-pwa) - [Cars](?pwaLob=wizard-car-pwa) # Sleepy Hollow, IL ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Midway Intl. ](https://www.expedia.com/Midway-Intl-Airport-Hotels.0-aMDW-0.Travel-Guide-Filter-Hotels) - [Hotels near Archer Heights ](https://www.expedia.com/Archer-Heights-Chicago-Hotels.0-n6132347-0.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Archer Heights ](https://www.expedia.com/Archer-Heights-Chicago-Hotels-Hotels-With-Complimentary-Breakfast.0-n6132347-0-tHotelswithComplimentaryBreakfast.Travel-Guide-Filter-Hotels) - 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