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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 (£69). Conversely, the most expensive month to stay in Uptown is August (£289).

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

The cheapest day to stay in Uptown is Monday (£151). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is £486.
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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 £258 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. 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
£258
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?

    220 reviews rated The Guesthouse Hotel with an average score of 9.5/10. It may also be worth looking into the The Bright Retreat in Andersonville, which received a rating of 9.4/10 from 38 reviews. Uptown Gem could also be a good option, with a score of 10.0/10 from 30 reviews.

  • What is a good hotel near Union Station?

    Reviews of Congress Plaza Hotel recommend it as a good place to stay near Union Station, scoring 7.3/10 from 7,801 ratings.

  • What is a good hotel in Uptown near McCormick Place?

    Hyatt Regency Mccormick Place is rated 8.5 from 2,855 reviews and is close to McCormick Place.

  • Is there a good hotel near Grant Park?

    If you’re looking for good hotels near Grant Park, consider Congress Plaza Hotel (rated 7.3 over 7,801 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 £232/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 Union Station located in Chicago, followed by McCormick Place and Grant Park, 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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Find better results for your stay in Uptown

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under £37 and Hotels Under £74. Discover hotel discounts now and make your hotel reservation today.