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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 ($236). Conversely, the most expensive month to stay in Uptown is November ($956).

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

The cheapest day to stay in Uptown is Wednesday ($257). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $569.

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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 $378 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 8 July 2026
Currently, these are the lowest-priced hotels in Uptown we've come across for the dates selected. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
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
$378
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 8 July 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 232 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 9.5/10 ratings from our users, respectively.

  • What is a good hotel near Millennium Knickerbocker Hotel Chicago?

    A good hotel close to Millennium Knickerbocker Hotel Chicago is Warwick Allerton Chicago (rated 8.1/10 from 6,950 reviews).

  • What is a good hotel in Uptown near Navy Pier?

    Warwick Allerton Chicago is rated 8.1 from 6,950 reviews and is close to Navy Pier.

  • Is there a good hotel near Grant Park?

    Close to Grant Park you will find River Hotel, which has a rating of 8.4 over 7,166 HotelsCombined reviews.

  • How much is a cheap hotel in Uptown?

    HotelsCombined users have found cheap hotels in Uptown starting from $379 per night in the last 3 days.

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

    The top three landmarks in Uptown are:
    • Millennium Knickerbocker Hotel Chicago, which you can visit while staying in Chicago
    • Navy Pier, which you can visit while staying in Chicago
    • Grant Park, which you can visit while staying in Chicago

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