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Hotels in Uptown, Chicago

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Travel insights for hotels in Uptown

Use our HotelsCombined data-powered tips to help you find your next hotel in Uptown.

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

The cheapest month to book a hotel in Uptown is March (£105). Conversely, the most expensive month to stay in Uptown is November (£700).

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

The cheapest day to stay in Uptown is Monday (£163). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is £394.

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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 £153 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 12 February 2026
Out of the hotels in Uptown we've come across, these properties are priced the lowest. 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
6.9 mi from city centre
Free Wi-Fi
£153
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 12 February 2026.

  • What are the best hotels in Uptown?

    232 reviews rated The Guesthouse Hotel with an average score of 9.3/10. It may also be worth looking into the Artistic Loft Rooftop Uptown Montrose Beach Gymwfh, which received a rating of 9.9/10 from 45 reviews. The Bright Retreat in Andersonville could also be a good option, with a score of 9.5/10 from 46 reviews.

  • What is a good hotel near Grant Park?

    Reviews of Congress Plaza Hotel Chicago recommend it as a good place to stay near Grant Park, scoring 7.3/10 from 9,263 ratings.

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

    Congress Plaza Hotel Chicago is rated 7.3 from 9,263 reviews and is close to Union Station.

  • Is there a good hotel near Magnificent Mile?

    If you’re looking for good hotels near Magnificent Mile, consider Freehand Chicago (rated 7.2 over 4,963 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 £147/night, depending on the popularity of your requested dates.

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

    The most popular landmark in Uptown is Grant Park located in Chicago, followed by Union Station and Magnificent Mile, located in Chicago and Chicago, respectively. Depending on where and how long you plan on staying in Uptown, you may be able to visit at least one of these cities.

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