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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 March (S$ 210). Conversely, the most expensive month to stay in Uptown is August (S$ 873).

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

The cheapest day to stay in Uptown is Monday (S$ 457). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is S$ 1,468.
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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$ 449 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 17 August 2025
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$ 449
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 17 August 2025.

  • What are the best hotels in Uptown?

    One of the most popular hotels in Uptown is The Guesthouse Hotel, which has been reviewed by 220 users and currently has a rating of 9.5/10. Other top-rated locations include The Bright Retreat in Andersonville and Uptown Gem, which have received 9.4/10 and 10.0/10 ratings from our users, respectively.

  • What is a good hotel near The Arc at Old Colony?

    With a rating of 8.2/10 from 1,325 reviews, Chicago Marriott Downtown Magnificent Mile is a hotel close to The Arc at Old Colony that is highly recommended by HotelsCombined users.

  • What is a good hotel in Uptown near Magnificent Mile?

    Hilton Chicago/Magnificent Mile Suites is a hotel near Magnificent Mile that is popular with HotelsCombined users, scoring 8.5 from 1,956 reviews.

  • Is there a good hotel near River North?

    Close to River North you will find Hilton Chicago/Magnificent Mile Suites, which has a rating of 8.5 over 1,956 HotelsCombined reviews.

  • How much is a cheap hotel in Uptown?

    S$ 403 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?

    The Arc at Old Colony, Magnificent Mile, and River North are the most popular landmarks in Uptown according to our data. You can experience The Arc at Old Colony if you plan to visit Chicago. You can visit Magnificent Mile if you stay in Chicago. River North is accessible while staying in Chicago.

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Consider alternative stays in Chicago

If you are looking for a specific type of hotel, consider these options for trips to Chicago
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