Title: Book the Best CHEAP Hotels in Uptown, Chicago from CA $399 - Uptown Cheap Hotels | Expedia.ca [Uptown Travel Guide](https://expedia.ca/Chicago-Uptown.dx6132444)[Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[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) ![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=1200&h=500&q=medium) # Find Cheap Hotels in Uptown, Chicago from CA $399 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Uptown Cheap Hotels Tonight [Nov 5 - Nov 6](https://www.expedia.ca/Hotel-Search?regionId=6132444&startDate=2025-11-05&endDate=2025-11-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Tomorrow [Nov 6 - Nov 7](https://www.expedia.ca/Hotel-Search?regionId=6132444&startDate=2025-11-06&endDate=2025-11-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132444&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6132444&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=budget_property) ## Top Uptown Cheap Hotels ![Rooftop terrace](https://images.trvl-media.com/lodging/17000000/16580000/16578800/16578746/35dc421f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/17000000/16580000/16578800/16578746/bbff9a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 3 Bedrooms, Kitchen | Living area](https://images.trvl-media.com/lodging/17000000/16580000/16578800/16578746/61869b3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/17000000/16580000/16578800/16578746/4baf2c9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Guesthouse Hotel Uptown 9.8/10 Exceptional (354) "Best place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward K CA $340 CA $399 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Chicago-Hotels-The-Guesthouse-Hotel.h16578746.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20®ionId=6132444&adults=2&travelerType=budget_property&sort=RECOMMENDED&openPlayBack=true) ## Top Uptown Hotel Reviews ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "It was great experience but middle of the night there was bagging then sounded like a drill going repairing something " [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](//images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10/10 Excellent "Clean rooms and friendly staff" [](https://expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Hotel Felix River North/Magnificent Mile](//images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d_y.jpg) ### Hotel Felix River North/Magnificent Mile 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![The Allegro Royal Sonesta Hotel Chicago Loop](//images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg) ### The Allegro Royal Sonesta Hotel Chicago Loop 10/10 Excellent "Good service " [](https://expedia.ca/Chicago-Hotels-The-Allegro-Royal-Sonesta-Hotel.h34496.Hotel-Information) ![Freehand Chicago](//images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg) ### Freehand Chicago 10/10 Excellent "Staff interactions were excellent in every aspect. " [](https://expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Great staff at the front desk!" [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Best upon arrival and the staff promptly answered any and all concerns" [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Palmer House a Hilton Hotel](//images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "Room was very clean and well kept" [](https://expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](//images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Everything was perfect will definitely stay again . " [](https://expedia.ca/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.Hotel-Information) ## Frequently asked questions ### What is Uptown like for travelers on a budget? > Discover discount places to stay in Uptown on Expedia.com and plan a trip that fits your budget. You can browse a wide offering of accommodations with Member Prices to score the best deal for you. Guided by our site's helpful page filters, you can limit results by your price range, or by top amenities like free parking and free WiFi. Or, try refining your search with the location filters to see affordable options around local attractions, such as Lake Michigan or Aragon Ballroom. While you browse, click the heart button to keep track of your favorites so that you can find them later when you're ready to book. Interested in a car or a flight too? Choose from the travel packages offered under Bundle and Save and discover huge discounts when you reserve your transportation at the same time. ### What is there to see and do in Uptown? > You don't need to spend a lot to find places to visit in Uptown. You can budget for the popular local attractions that are highest on your list, such as Wrigley Field and Michigan Avenue, and choose other low-cost activities to fill your itinerary. Enjoy the outdoors at Lake Michigan and Montrose Beach, or hunt for bargains with some shopping at Navy Pier. ### How can I get to Uptown and get around on a budget? > Scoping out the transportation options in Uptown is a smart way to keep your trip affordable. The nearest airport is Chicago O'Hare Intl. Airport (ORD), situated 12.9 mi (20.8 km) away. However, if that doesn't suit your budget, you can arrange flights in and out of Chicago Midway Airport (MDW), which is 13 mi (21 km) away. 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[Wrigleyville Hotels](https://www.expedia.ca/Wrigleyville-Chicago-Hotels.0-n6338684-0.Travel-Guide-Filter-Hotels) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Aragon Ballroom](https://www.expedia.ca/Aragon-Ballroom-Uptown.d553248621563220754.Vacation-Attraction) - [Visit Lakeview](https://www.expedia.ca/Chicago-Lakeview.dx178166) - [Visit Lakewood-Balmoral](https://www.expedia.ca/Chicago-Lakewood-Balmoral.dx553248635976479852) - [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) - [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) - [Book Hotels in Uptown on Expedia.com](https://www.expedia.com/Uptown-Chicago-Hotels-Cheap-Hotels.0-n6132444-0-tCheapHotels.Travel-Guide-Filter-Hotels)