Hotels in Uptown, Chicago

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Recommended by KAYAK
Booking Insights
Recommended by KAYAK

Best hotels in Uptown (Chicago)

These are the best prices for 29 Jul - 5 Aug.
The Guesthouse Hotel - Chicago - Balcony
The Guesthouse Hotel
0.9 mi from Uptown, Chicago, United States
9.2Wonderful(232)
Free Wi-Fi
Pet-friendly
Air conditioning
£446+
Check availability
Uptown Gem - Chicago
Uptown Gem
0.3 mi from Uptown, Chicago, United States
9.4Wonderful(32)
Parking
Free Wi-Fi
Pool
Air conditioning
£346+
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 £176/night. In comparison, November is the most expensive month, with prices at £713/night.

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

Friday offers the lowest rates in Uptown, with an average nightly price of £311/night. The highest prices are found on Wednesday, with average rates at £699/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

February
November
Cheapest month to stay with an average 35% drop in price.
Most expensive month to stay with an average 163% rise in price.

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 September and October.
  • Not sure just how much there is to see and do in Uptown? KAYAK users usually book their hotel here for 3 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 The Bright Retreat in Andersonville 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.

Everything you need to know for your stay in Chicago