Title: Visit Uptown: Best of Uptown, Chicago Travel 2026 | Expedia Tourism - Expedia.ca [Hotels in Uptown](https://expedia.ca/Uptown-Chicago-Hotels.0-n6132444-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Uptown Car Rentals](https://expedia.ca/Car-Rentals-In-Uptown.d6132444.Car-Rental-Guide)[Uptown Vacations](https://expedia.ca/Uptown.d6132444.Destination-Travel-Guides) # Uptown ## Chicago ![Montrose Beach which includes a sandy beach and general coastal views as well as an individual male](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298063-Montrose-Beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Montrose Beach which includes general coastal views and a beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298060-Montrose-Beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Montrose Beach which includes general coastal views and a beach as well as a couple](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298062-Montrose-Beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Montrose Harbor showing bird life, a sunset and a bay or harbour](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298084-Montrose-Harbor.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Montrose Beach which includes general coastal views, swimming and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298061-Montrose-Beach.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Uptown Things to do Hotels Where to stay [Chicago travel guide](https://expedia.ca/Chicago.dx178248) --- ### Popular places to visit ![Montrose Beach which includes a city, a sandy beach and a coastal town](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298066-Montrose-Beach.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montrose Beach Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities. [](https://expedia.ca/Montrose-Beach-Uptown.d6277595.Vacation-Attraction) ![Montrose Harbor showing a bay or harbour and bird life](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298085-Montrose-Harbor.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montrose Harbor With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out. [](https://expedia.ca/Montrose-Harbor-Uptown.d6277593.Vacation-Attraction) ![Hutchinson Street Historic District](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543375-chicago.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Hutchinson Street Historic District You can learn about the history of Chicago when you stop by Hutchinson Street Historic District. Experience the entertainment choices and acclaimed theater scene in this vibrant area. [](https://expedia.ca/Hutchinson-Street-District-Chicago.d553248621533116620.Vacation-Attraction) #### Aragon Ballroom Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices. [](https://expedia.ca/Aragon-Ballroom-Uptown.d553248621563220754.Vacation-Attraction) #### Riviera Theatre You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene. [](https://expedia.ca/Riviera-Theatre-Uptown.d553248621555594761.Vacation-Attraction) #### Louis A. Weiss Memorial Hospital Though Louis A. Weiss Memorial Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here. [](https://expedia.ca/Louis-A-Weiss-Memorial-Hospital-Uptown.d6182913.Vacation-Attraction) ### Things to do ![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 CA $48 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Spirit of Chicago Lunch Cruise](https://mediaim.expedia.com/localexpert/793486/dc2cc19e-2c27-474c-b603-64f1b23a2df6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Spirit of Chicago Signature Lunch Cruise on Lake Michigan CA $136 per adult [](https://expedia.ca/things-to-do/spirit-of-chicago-signature-lunch-cruise-on-lake-michigan.a793486.activity-details) ![Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting](https://mediaim.expedia.com/localexpert/4973725/0b36f3b1-b375-4fa2-8cfd-1a9815dcdcdc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting CA $50 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/medieval-torture-museum-ticket-with-audio-guide-and-ghost-hunting.a4973725.activity-details) ![Chicago's Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/48840807/8856f18f-7399-4c59-bffa-336edc781f23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago's Navy Pier Centennial Wheel Ticket CA $34 per adult [](https://expedia.ca/things-to-do/chicagos-navy-pier-centennial-wheel-ticket.a48840807.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 CA $285 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.activity-details) ![Chicago: City Minibus Tour with Optional Architecture Cruise](https://mediaim.expedia.com/localexpert/4556313/67d8adf7-64e5-458d-bd4c-e2cc830c3f09.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago: City Minibus Tour with Optional Architecture Cruise CA $69 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-city-minibus-tour-with-optional-architecture-cruise.a4556313.activity-details) [See all activities in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) --- ## Uptown Hotel Deals ![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 CA $138 CA $162 total Jan 4 - Jan 5, 2026 includes taxes & 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 ... 8.4/10 Very Good! (5,356 reviews) Very clean room, great breakfast, and very quick response to request for extra blankets. Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132444) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL CA $112 CA $131 total Jan 5 - Jan 6, 2026 includes taxes & 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 ... 8.8/10 Excellent! (3,464 reviews) I love the big asize of the room. The bed was comfortable. The room temperature was warm and pleasant even as it snowed outside the windows. The only downside would be when I went to watch the Sunday night Bears and Packers football game down at the bar. The young and bearded bartender swore like ... Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F01%2F2026&endDate=06%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132444) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL CA $111 CA $173 total Dec 21 - Dec 22 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ... 9.2/10 Wonderful! (2,107 reviews) First of all, the staff and bartender at this hotel were extremely friendly and helpful. Check-in and check-out were quick and easy. We chose valet parking to ease that portion of our travels, and that aspect was very smooth and efficient. The property itself was clean and quiet, but the area around ... Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=6132444) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL CA $153 CA $213 total Dec 21 - Dec 22 includes taxes & fees Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ... 8.4/10 Very Good! (2,131 reviews) Great room with double bathroom. Executive level with private elevator. Reviewed on Dec 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=6132444) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eurostars Magnificent Mile 660 North State Street Chicago IL CA $119 CA $140 total Jan 11 - Jan 12, 2026 includes taxes & fees Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ... 8.8/10 Excellent! (3,148 reviews) Overall stay was great! The staff and valet were very polite. My only complaint is there was hair in the shower when we checked in. Cleanliness there could be improved. I just washed it down the drain but it wasn’t pleasant to see. Otherwise, the hotel was very nice, close to many things & valet ... Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=1880320&PinnedHotelID=1880320&HadPinnedHotel=true®ionId=6132444) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel Wacker at Michigan, Chicago 75 E Wacker Dr Chicago IL CA $102 CA $120 total Dec 29 - Dec 30 includes taxes & fees Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ... 8.6/10 Excellent! (1,966 reviews) We loved the hotel, parking was a bit of a ways off. Reviewed on Dec 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=29%2F12%2F2025&endDate=30%2F12%2F2025&selected=889753&PinnedHotelID=889753&HadPinnedHotel=true®ionId=6132444) [See all 4,755 properties in Uptown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=13%2F12%2F2025&endDate=14%2F12%2F2025®ionId=6132444) 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 Uptown hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2025-12-12&endDate=2025-12-13)[Dec 12 - Dec 13](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2025-12-12&endDate=2025-12-13) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2025-12-13&endDate=2025-12-14)[Dec 13 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2025-12-13&endDate=2025-12-14) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=12%2F12%2F2025&endDate=14%2F12%2F2025)[Dec 12 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=12%2F12%2F2025&endDate=14%2F12%2F2025) --- ### Other neighbourhoods around Uptown ![Wrigley Field showing signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35621-Wrigley-Field.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Wrigleyville You might enjoy the bars while in Wrigleyville. Wrigley Field is a notable sight, and you can get around town at Sheridan Station or Addison Station (Red Line) to see more of the city. [](https://expedia.ca/Chicago-Wrigleyville.dx6338684) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191788-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lakeview 5/5(30 area reviews) Known for its great bars and fantastic lake views, there's plenty to explore in Lakeview. You can visit top attractions like Wrigley Field and Lake Michigan, and jump on the metro at Southport Station or Addison Station (Red Line) to see more of the city. [](https://expedia.ca/Chicago-Lakeview.dx178166) ![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Lincoln Park 5/5(20 area reviews) Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [](https://expedia.ca/Chicago-Lincoln-Park.dx6059328) ![Default Image](https://mediaim.expedia.com/destination/2/11fd6e63e168e646892c8441abd32c9c.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Old Town Chicago Known for its ample dining options and fantastic lake views, there's plenty to explore in Old Town Chicago. You can visit top attractions like Second City and Armitage Avenue, and jump on the metro at Sedgwick Station or Clark-Division Station to see more of the city. [](https://expedia.ca/Chicago-Old-Town-Chicago.dx6351828) ![Default Image](https://mediaim.expedia.com/destination/2/8243ae66c409b6b794c27f18c913d92f.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.ca/Chicago-Wicker-Park.dx6227639) ![Gold Coast featuring street scenes as well as a couple](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191825-Gold-Coast.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Gold Coast The abundant dining options and lake views are top of the list for many visitors to Gold Coast. A stop by Michigan Avenue or Lake Michigan might round out your trip. 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