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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 September ($168). Conversely, the most expensive month to stay in Uptown is August ($446).
What is the cheapest day to stay in a hotel in Uptown?
The cheapest day to stay in Uptown is Tuesday ($152). On the other hand, travelers can expect to pay the most on Wednesday, when the average nightly price is $435.
Discover affordable stays in Uptown that provide a quality experience without breaking the bank. Hotels in Uptown can be found for as low as $393 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 1 May 2025
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.
Find useful tips and insights about staying in Uptown to help you make the most of your experience. FAQs were last updated on 1 May 2025.
What are the best hotels in Uptown?
One of the most popular hotels in Uptown is The Guesthouse Hotel, which has been reviewed by 216 users and currently has a rating of 9.6/10. Other top-rated locations include The Bright Retreat in Andersonville and Uptown Gem, which have received 9.2/10 and 9.9/10 ratings from our users, respectively.
What is a good hotel near McCormick Place?
A good hotel close to McCormick Place is Hyatt Regency Mccormick Place (rated 8.6/10 from 2,821 reviews).
What is a good hotel in Uptown near Union Station?
Freehand Chicago is rated 7.3 from 4,698 reviews and is close to Union Station.
Is there a good hotel near Grant Park?
Close to Grant Park you will find Freehand Chicago, which has a rating of 7.3 over 4,698 HotelsCombined reviews.
How much is a cheap hotel in Uptown?
HotelsCombined users have found cheap hotels in Uptown starting from $367 per night in the last 3 days.
What are the most popular landmarks to visit in Uptown?
The top three landmarks in Uptown are: • McCormick Place, which you can visit while staying in Chicago • Union Station, which you can visit while staying in Chicago • Grant Park, which you can visit while staying in Chicago
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