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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 ($404). Conversely, the most expensive month to stay in Uptown is November ($1,636).

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

The cheapest day to stay in Uptown is Wednesday ($439). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,035.

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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 $633 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 18 July 2026
These Uptown properties charge the lowest price per night of those we've come across. If you have the flexibility, change the dates selected to compare prices.
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
$633
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 18 July 2026.

  • What are the best hotels in Uptown?

    The Guesthouse Hotel, rated with a score of 9.2 from 232 reviewers, is one of the most popular hotels in Uptown. Other top stays include Artistic Loft Rooftop Uptown Montrose Beach Gymwfh, with an average rating of 9.9 from 50 reviewers, and The Bright Retreat in Andersonville, with a score of 9.5 from 49 reviewers.

  • What is a good hotel near Wrigley Field?

    With a rating of 7.9/10 from 2,238 reviews, Hotel Versey Chicago Lincoln Park is a hotel close to Wrigley Field that is highly recommended by HotelsCombined users.

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

    Warwick Allerton Chicago is rated 8.1 from 6,941 reviews and is close to Magnificent Mile.

  • Is there a good hotel near Grant Park?

    A good hotel near Grant Park is River Hotel, which has been rated 8.4/10 by 7,229 HotelsCombined user reviews.

  • How much is a cheap hotel in Uptown?

    HotelsCombined searches in the last 3 days suggest cheap Uptown hotels have prices starting from as low as $649/night, depending on the popularity of your requested dates.

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

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

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