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 ![EyeEm Custom Shoots Q4 2018](https://images.trvl-media.com/place/6132444/bc1230a6-8e59-4c7a-b058-9b6381d46b9e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Timing is everything. If I tried to take this shot a million times I would never be able to duplicate the position of the sun in her tires. She was moving very quickly when I took this shot. ](https://images.trvl-media.com/place/829/528bc138-02e8-461a-bcc1-cf2306c62aaf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A white sulphur butterfly on a purple wildflower in the meadow at Montrose Beach. ](https://images.trvl-media.com/place/829/bb8b0c8b-8dd5-4705-8a01-a85cae814076.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A group of semi palmated sandpipers migrating along the Chicago lakefront that landed in the biggest and best migrant trap in the area.](https://images.trvl-media.com/place/829/3c85aa39-0a70-4e65-88b5-90034f1e6746.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A pair of bonapartes gulls in the dunes at Montrose. These are handsome gulls that are smaller than ring billed gulls and somewhat unusual in Chicago. I wish they had the black head of the breeding bonapartes but these appear to be young ones that are in their first year.](https://images.trvl-media.com/place/829/d8b90d81-aa21-424e-906e-eff7c532af7c.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 ![Chicago_AragonBallroom_553248621563220754](https://images.trvl-media.com/place/553248621563220754/b4e6b016-0630-4b72-a6d9-2d42813bdd17.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Aragon Ballroom Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene. [](https://expedia.ca/Aragon-Ballroom-Uptown.d553248621563220754.Vacation-Attraction) ![Montrose Beach which includes a city, a sandy beach and a coastal town](https://images.trvl-media.com/place/6277595/33eea866-186b-47ad-8add-7a479ffd7597.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://images.trvl-media.com/place/6277593/c88517b0-88ba-42f0-bd30-4d09f688bf7b.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 which includes motorcycle riding and street scenes](https://images.trvl-media.com/place/553248621533116620/c09d7bfc-3709-4eab-89c4-50a85119f235.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 acclaimed theater scene and entertainment choices in this vibrant area. [](https://expedia.ca/Hutchinson-Street-District-Chicago.d553248621533116620.Vacation-Attraction) !["Eternal Silence" is a monument in Chicago's Graceland Cemetery. It is a 10ft tall bronze sculpture set on and backdropped by black granite. Also referred to as the Statue of Death, it was created by American sculptor Lorado Taft in 1909. It is a monument to Dexter Graves, who brought the first colony to Chicago consisting of thirteen families who moved from Ashtabula, Ohio in 1831](https://images.trvl-media.com/place/829/4d4deb88-1236-437b-8f2d-571dfe91ed02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Graceland Cemetery Enjoy a stop at Graceland Cemetery, a landmark worth seeing in Chicago. Experience the entertainment choices and acclaimed theater scene in this vibrant area. [](https://expedia.ca/Graceland-Cemetery-Uptown.d553248621533116619.Vacation-Attraction) ![Wrigley Field featuring central business district, a city and a sporting event](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(158 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.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 CA $36 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.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 CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/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 CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) [See all activities in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities) --- ## Uptown 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 CA $132 CA $155 total Apr 1 - Apr 2 includes taxes & 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! (9,922 reviews) The location is amazing, right on Michigan Avenue, across the street from the park, a few blocks south of the river. The staff was friendly and efficient when I checked in, asked a few questions, and checked out. The room was great... nicer than I imagined. I would have liked daily room service. ... Reviewed on Mar 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=6132444) ![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 CA $181 CA $251 total Mar 22 - Mar 23 includes taxes & 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! (3,527 reviews) Clean, central and amazing breakfast Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=6132444) ![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 CA $178 CA $209 total Mar 23 - Mar 24 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 ... 8.6/10 Excellent! (5,737 reviews) Clean property overall, cleaning staff did not clean our room daily and we had to ask for towels and wash clothes. It is close and in walking distance of restaurants and shopping. Reviewed on Mar 14, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132444) ![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 CA $142 CA $166 total Mar 23 - Mar 24 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 ... 9/10 Wonderful! (3,910 reviews) location and room met expectations Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132444) ![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 CA $269 CA $316 total Apr 3 - Apr 4 includes taxes & 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! (2,220 reviews) Pricey but right at the airport. Works so conveniently for us to come in by bus or CTA. Love eating at the bar restaurant. Reviewed on Mar 13, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=6132444) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eurostars Magnificent Mile 660 North State Street Chicago IL Fully refundableReserve now, pay when you stay CA $196 CA $230 total Mar 17 - Mar 18 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 ... 9/10 Wonderful! (3,305 reviews) Friendly staff Reviewed on Mar 12, 2026 [](https://expedia.ca/Hotel-Search?startDate=17%2F03%2F2026&endDate=18%2F03%2F2026&selected=1880320&PinnedHotelID=1880320&HadPinnedHotel=true®ionId=6132444) [See all 4,742 properties in Uptown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=15%2F03%2F2026&endDate=16%2F03%2F2026®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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=DX-NH_SPRING_PROMO_6132444) ## Check Uptown hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-03-14&endDate=2026-03-15)[Mar 14 - Mar 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-03-14&endDate=2026-03-15) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-03-15&endDate=2026-03-16)[Mar 15 - Mar 16](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-03-15&endDate=2026-03-16) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026)[Mar 20 - Mar 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026) --- ### Other neighbourhoods around Uptown ![Cubs/Brewers game](https://images.trvl-media.com/place/829/a351d868-663b-4e01-8404-d79b6bc1c863.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) ![Lakeview featuring modern architecture](https://images.trvl-media.com/place/178166/66f7ee9b-8e1a-4caa-8412-e82732aa12d8.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://images.trvl-media.com/place/6059328/2fb61786-4c0f-40e8-ae4e-a0fad3f9539a.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) ![Old Town Chicago Neighborhood entrance gate and sign](https://images.trvl-media.com/place/6351828/4c85d549-19ea-45b5-aa00-283c75b184b6.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) ![Chicago_LoganSquare_6132429_04](https://images.trvl-media.com/place/6132429/9b00bf25-0a43-42b8-9beb-9c7c565c05fa.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Logan Square Get to know Logan Square and its many features like its breweries and live music. You might want to explore sights like Concord Music Hall and Milwaukee Avenue, and you can jump on the metro at Logan Square Station or California Station (Blue Line) to get around the city. [](https://expedia.ca/Chicago-Logan-Square.dx6132429) ![Wicker Park Historic District, a residential neighbourhood, Chicago, Illinois, USA](https://images.trvl-media.com/place/6227639/a89281f3-851c-4c74-8025-215bb2cb4b7b.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. 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