Insights
Cheapest hotels
Where to stay

Hotels in Uptown, Chicago

Search and compare Uptown, Chicago hotels from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customize your results by hotel chain, amenities, price, and more.

Search for hotels as many times as you want – for free.

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 March (C$ 237). Conversely, the most expensive month to stay in Uptown is August (C$ 1,122).

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

The cheapest day to stay in Uptown is Sunday (C$ 414). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 1,106.
Find deals

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 C$ 500 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 3 July 2025
At the moment, these hotels offer the lowest nightly rate out of those we've come across in Uptown. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
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
C$ 500
Avg. per night
View Deal

Where to stay in Uptown

Explore different neighbourhoods and areas within Uptown to find the perfect location for your stay. Map data was last updated on 3 July 2025.
Scroll through the map to find hotels close to the Uptown neighborhood(s) you plan on visiting. More information on a given hotel can be accessed by clicking the hotel's name within the map.

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 3 July 2025.

  • What are the best hotels in Uptown?

    The Guesthouse Hotel (9.5/10 from 219 reviews), The Bright Retreat in Andersonville (9.2/10 from 27 reviews), and Uptown Gem (9.9/10 from 30 reviews) are all highly rated places to stay in Uptown.

  • What is a good hotel near Magnificent Mile?

    A good hotel close to Magnificent Mile is Freehand Chicago (rated 7.3/10 from 4,771 reviews).

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

    Hyatt Regency Mccormick Place is the most recommended hotel near McCormick Place on HotelsCombined (scoring 8.5 over 2,837 reviews).

  • Is there a good hotel near River North?

    If you’re visiting River North then the nearby Freehand Chicago is a popular hotel with HotelsCombined users (4,771 reviews scoring it at an average 7.3/10).

  • How much is a cheap hotel in Uptown?

    Prices for Uptown hotels have been found for as low as C$ 500/night over the last 3 days.

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

    Magnificent Mile, McCormick Place, and River North are the most popular landmarks in Uptown according to our data. You can experience Magnificent Mile if you plan to visit Chicago. You can visit McCormick Place if you stay in Chicago. River North is accessible while staying in Chicago.

See more FAQs

Find better results for your stay in Uptown

Consider these popular 4-star hotels in Uptown

Stay at one of these Uptown 4-star hotels that users have found on HotelsCombined.
The Guesthouse Hotel