Hotels in Uptown

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Check prices for these dates

Tonight
Dec 14 - Dec 15
Tomorrow
Dec 15 - Dec 16
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Where to stay in Uptown?

Rooftop terrace
The Guesthouse Hotel

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (363)
The price is $200
$235 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Guesthouse Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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When is the best time to visit Chicago?

Our prices for hotels in Chicago are cheapest in January
Price trends for hotels in Chicago
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Chicago
December
High crowds
High 3°C / low -2°C. Cloudy most days.
View properties in December
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December, High crowds, average high temperature 3 degrees Celsius, average low temperature -2 degrees Celsius. Cloudy most days.
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January, Low crowds, average high temperature -1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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February, Low crowds, average high temperature 0 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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March, Low crowds, average high temperature 6 degrees Celsius, average low temperature 0 degrees Celsius. Cloudy most days.
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April, Low crowds, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Partly sunny.
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May, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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23°
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June, High crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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August, High crowds, average high temperature 26 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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September, Moderate crowds, average high temperature 23 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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October, Moderate crowds, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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November, Moderate crowds, average high temperature 8 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
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Monthly weather averages (˚C)

Top landmarks in Uptown

Chicago_AragonBallroom_553248621563220754

Aragon Ballroom

You could catch an event at Aragon Ballroom, a stadium in Uptown. Let yourself be amazed at the art galleries in the area— your cultural tour starts here. If you think Aragon Ballroom is cool, you also might like Wrigley Field and Wrigley View Rooftop, both located nearby.
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Montrose Beach in Uptown Chicago during the Summer with the Edgewater Skyline

Montrose Beach

If being by the water is a major draw, Montrose Beach is a spot you might want to check out, located 6.1 mi (9.9 km) from central Chicago. If you want to continue walking by the waves, head to Foster Avenue Beach located nearby.
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Check out reviews of Uptown hotels guests love

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Very convenient to museums, trains, music and restaurants. 24 hour coffee and tea. Staff very nice. Would stay there again!"
Blannie 4-night trip
Posted 15 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop
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