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Hotels in Uptown, Chicago

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Travel insights for hotels in Uptown

Use these up-to-date, data-driven insights about booking a hotel in Uptown including ideal times to book, pricing trends, and more.

What is the cheapest month to book a hotel in Uptown?

The cheapest month to book a hotel in Uptown is February (S$ 303). Conversely, the most expensive month to stay in Uptown is November (S$ 1,230).

What is the cheapest day to stay in a hotel in Uptown?

The cheapest day to stay in Uptown is Friday (S$ 236). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 693.

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Cheapest hotels in Uptown, Chicago

Discover affordable stays in Uptown that provide a quality experience without breaking the bank. Hotels in Uptown can be found for as low as S$ 271 per night. There is currently one property in Uptown that can be booked for this price. The Guesthouse Hotel is one of the hotels that can be booked for the lowest price in Uptown. Price data was last updated on 14 January 2026
Out of the hotels in Uptown we've come across, these properties are priced the lowest. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
The Guesthouse Hotel
The Guesthouse Hotel

The Guesthouse Hotel

4872 N Clark Street, Chicago, IL, United States
11.1 km from city centre
Free Wi-Fi
S$ 271
Avg. per night
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Facts about staying in Uptown, Chicago

Find useful tips and insights about staying in Uptown to help you make the most of your experience. FAQs were last updated on 14 January 2026.

  • What are the best hotels in Uptown?

    One of the most popular hotels in Uptown is The Guesthouse Hotel, which has been reviewed by 231 users and currently has a rating of 9.2/10. Other top-rated locations include Artistic Loft Rooftop Uptown Montrose Beach Gymwfh and The Bright Retreat in Andersonville, which have received 9.9/10 and 9.4/10 ratings from our users, respectively.

  • What is a good hotel near Grant Park?

    With a rating of 7.3/10 from 8,035 reviews, Congress Plaza Hotel is a hotel close to Grant Park that is highly recommended by HotelsCombined users.

  • What is a good hotel in Uptown near Union Station?

    Congress Plaza Hotel is a hotel near Union Station that is popular with HotelsCombined users, scoring 7.3 from 8,035 reviews.

  • Is there a good hotel near Magnificent Mile?

    Close to Magnificent Mile you will find River Hotel, which has a rating of 8.3 over 5,389 HotelsCombined reviews.

  • How much is a cheap hotel in Uptown?

    S$ 282 per night is the cheapest Uptown hotel price found in our data from the last 72 hours.

  • What are the most popular landmarks to visit in Uptown?

    Grant Park, Union Station, and Magnificent Mile are the most popular landmarks in Uptown according to our data. You can experience Grant Park if you plan to visit Chicago. You can visit Union Station if you stay in Chicago. Magnificent Mile is accessible while staying in Chicago.

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