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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 December (£136). Conversely, the most expensive month to stay in Uptown is November (£708).

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

The cheapest day to stay in Uptown is Monday (£118). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is £700.

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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 £157 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 28 December 2025
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
£157
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 28 December 2025.

  • What are the best hotels in Uptown?

    231 reviews rated The Guesthouse Hotel with an average score of 9.4/10. It may also be worth looking into the Artistic Loft Rooftop Uptown Montrose Beach Gymwfh, which received a rating of 9.9/10 from 40 reviews. The Bright Retreat in Andersonville could also be a good option, with a score of 9.4/10 from 43 reviews.

  • What is a good hotel near Grant Park?

    Reviews of Congress Plaza Hotel recommend it as a good place to stay near Grant Park, scoring 7.3/10 from 8,022 ratings.

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

    Congress Plaza Hotel is rated 7.3 from 8,022 reviews and is close to Union Station.

  • Is there a good hotel near McCormick Place?

    If you’re looking for good hotels near McCormick Place, consider Hyatt Regency Mccormick Place (rated 8.5 over 2,888 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 £161/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 McCormick Place, 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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