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) ![Uptown](https://images.trvl-media.com/place/829/528bc138-02e8-461a-bcc1-cf2306c62aaf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Uptown](https://images.trvl-media.com/place/829/bb8b0c8b-8dd5-4705-8a01-a85cae814076.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Uptown](https://images.trvl-media.com/place/829/3c85aa39-0a70-4e65-88b5-90034f1e6746.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Uptown](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](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](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) ![Graceland Cemetery](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) ![Hutchinson Street Historic District](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) ![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(159 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 $37 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.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) ![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 $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.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 $151 CA $177 total Apr 5 - Apr 6 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! (10,032 reviews) The whole place felt a little outdated. I know it is an old hotel, but some of these things could definitely be upgraded. The fridge in the room was set low and froze everything. You couldn’t control the temperature in the room, and I couldn’t have the windows open because there were no screens in ... Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=6452&PinnedHotelID=6452&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 Fully refundableReserve now, pay when you stay CA $191 CA $224 total Apr 12 - Apr 13 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! (4,024 reviews) Very nice Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=18514&PinnedHotelID=18514&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 Fully refundableReserve now, pay when you stay CA $198 CA $233 total Apr 12 - Apr 13 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! (5,801 reviews) The breakfast was fresh and staff was friendly and hospitable. John greeted us every morning for breakfast and was a pleasure to talk to. This wasn't a 5 start hotel but the staff made it feel like one. I'll be staying here for my next visit without a doubt. Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=12%2F04%2F2026&endDate=13%2F04%2F2026&selected=11580&PinnedHotelID=11580&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 $179 CA $250 total Apr 5 - Apr 6 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! (3,696 reviews) Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=102622712&PinnedHotelID=102622712&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 $346 CA $407 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! (2,242 reviews) The hotel environment is very nice. Clean room，friendly staff Reviewed on Apr 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=03%2F04%2F2026&endDate=04%2F04%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=6132444) ![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 CA $235 CA $276 total Apr 6 - Apr 7 includes taxes & 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! (1,763 reviews) Lake/Beach view was great, we were switched rooms, our room was not yet cleaned yet Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=1346&PinnedHotelID=1346&HadPinnedHotel=true®ionId=6132444) [See all 4,695 properties in Uptown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=02%2F04%2F2026&endDate=03%2F04%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. ## Check Uptown hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-04-01&endDate=2026-04-02)[Apr 1 - Apr 2](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-04-01&endDate=2026-04-02) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-04-02&endDate=2026-04-03)[Apr 2 - Apr 3](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=2026-04-02&endDate=2026-04-03) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[Apr 10 - Apr 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6132444&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026) --- ### Other neighbourhoods around Uptown ![Wrigleyville](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](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) ![Lincoln Park](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) ![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.ca/Chicago-Wicker-Park.dx6227639) ![Gold Coast](https://images.trvl-media.com/place/6130105/4c5121ee-a8cb-4bab-939d-ed9940fa17fb.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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[Visit Wicker Park ](https://www.expedia.ca/Chicago-Wicker-Park.dx6227639) - [Visit Winchester-Hood Garden Homes ](https://www.expedia.ca/Chicago-Winchester-Hood-Garden-Homes.dx553248635976470531) - [Visit Wrigleyville ](https://www.expedia.ca/Chicago-Wrigleyville.dx6338684) - [Lakeview Vacations ](https://www.expedia.ca/Lakeview.d178166.Destination-Travel-Guides) - [Montrose Beach ](https://www.expedia.ca/Montrose-Beach-Uptown.d6277595.Vacation-Attraction) - [Riviera Theatre ](https://www.expedia.ca/Riviera-Theatre-Uptown.d553248621555594761.Vacation-Attraction) - [Visit Rush Street ](https://www.expedia.ca/Rush-Street.dx6175183) - [Wrigley Field ](https://www.expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) - [Car rentals near Lakeview ](https://www.expedia.ca/Car-Rentals-In-Lakeview.d178166.Car-Rental-Guide) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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