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Hotels in Uptown, Chicago

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Booking Insights
Recommended by KAYAK

Best hotels in Uptown (Chicago)

These are the best prices for Oct 10 - 11.
The Guesthouse Hotel - Chicago - Balcony
The Guesthouse Hotel
0.9 mi from Uptown, Chicago, United States
9.1Wonderful(235)
Free Wi-Fi
Pet friendly
$492+
Check availability
Uptown Gem - Chicago
Uptown Gem
0.3 mi from Uptown, Chicago, United States
9.3Wonderful(33)
Parking
Free Wi-Fi
Pool
$294+
Check availability
Booking Insights

KAYAK’s insights for hotels in Uptown

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Uptown with confidence.

Which month has the cheapest hotel rates in Uptown?

Hotels are cheapest in Uptown in February, with average rates of $236/night. In comparison, September is the most expensive month, with prices at $866/night.

What is the cheapest day of the week to book a hotel in Uptown?

Wednesday offers the lowest rates in Uptown, with an average nightly price of $246/night. The highest prices are found on Thursday, with average rates at $827/night.

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How much is a Uptown hotel?

Here are our most popular & best value hotels

Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

February
September
$650
$525
Cheapest month to stay with an average 50% drop in price.
Most expensive month to stay with an average 84% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

Top tips for finding a hotel deal in Uptown

  • If you’re looking for a cheap hotel in Uptown, you should consider going during the low season. You’ll generally find lower-priced hotels in Uptown in February and March.
  • If you’re looking for a bargain then KAYAK data shows that you’ll find the best hotel deals in Uptown (Chicago) if you stay on a Wednesday. On the other hand, the most expensive day for hotel bookings is Thursday.
  • If you’re looking for a last minute bargain, the cheapest 3-star hotel in Uptown (Chicago) found on KAYAK in the last 2 weeks was $422, while the most expensive was $565.
  • Not sure just how much there is to see and do in Uptown? KAYAK users usually book their hotel here for 2 days.

FAQs when booking a hotel in Uptown

  • What are the best hotels in Uptown?

    Uptown is a great part of Chicago to make your base. If you’re staying in Uptown area then The Guesthouse Hotel, Artistic Loft Rooftop Uptown Montrose Beach Gymwfh, and Regal Stylish Uptown Loft Beachfront Rooftopwfhgym are all recommended on KAYAK.

Where to stay in Uptown?

Our map will help you find the perfect hotel in Uptown, Chicago by showing you the exact location of each hotel.

More options for your stay in Chicago