Hotels in Uptown, Chicago

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Booking Insights
Recommended by KAYAK

Best hotels in Uptown (Chicago)

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4+ stars

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6+ Okay7+ Good8+ Great9+ Excellent

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$52 - $347$347 - $641$641 - $935$935 - $1,229$1,229+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended Uptown hotels

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The Guesthouse Hotel - Chicago - Balcony
The Guesthouse Hotel
0.9 mi from Uptown, Chicago, United States
9.5Wonderful(223)
Free Wi-Fi
Pet friendly
$423+
Check availability
The Bright Retreat in Andersonville - Chicago - Living room
The Bright Retreat in Andersonville
0.9 mi from Uptown, Chicago, United States
9.4Wonderful(42)
Parking
Free Wi-Fi
$226+
Check availability
Inviting Stylish Home with Covered Patio - Chicago - Living room
Inviting Stylish Home with Covered Patio
0.7 mi from Uptown, Chicago, United States
9.0Wonderful(10)
Free Wi-Fi
$427+
Check availability
Walk to Wrigley Field/Monthly Discounts Available - Chicago - Balcony
Walk to Wrigley Field/Monthly Discounts Available
0.9 mi from Uptown, Chicago, United States
9.5Wonderful(122)
Free Wi-Fi
$320+
Check availability
Montrose Studio:Your Uptown Base - Chicago - Bedroom
Montrose Studio:Your Uptown Base
0.3 mi from Uptown, Chicago, United States
$187+
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Family Friendly 2bd/2ba Near Wrigley, Lincoln Square - Chicago - Balcony
Family Friendly 2bd/2ba Near Wrigley, Lincoln Square
0.8 mi from Uptown, Chicago, United States
10Wonderful(18)
$554+
Check availability
Uptown Studio Gem Sum - Chicago - Bedroom
Uptown Studio Gem Sum
0.3 mi from Uptown, Chicago, United States
$184+
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13 mins DT|4 mins Lake | Majestic Modern Style - Chicago - Balcony
13 mins DT|4 mins Lake | Majestic Modern Style
0.4 mi from Uptown, Chicago, United States
9.1Wonderful(9)
$266+
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Great Location-Beautiful Friendly Andersonville Neighborhood - Chicago - Living room
Great Location-Beautiful Friendly Andersonville Neighborhood
1.1 mi from Uptown, Chicago, United States
9.9Wonderful(54)
Free Wi-Fi
$333+
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Sunny Studio in Heart of Ravenswood - Chicago - Kitchen
Sunny Studio in Heart of Ravenswood
0.9 mi from Uptown, Chicago, United States
$213+
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Elegant 2BR Apartment w/ In-Unit Laundry - Chicago - Bedroom
Elegant 2BR Apartment w/ In-Unit Laundry
0.2 mi from Uptown, Chicago, United States
$238+
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Spacious and Airy Apartment for Big Groups! - Chicago - Living room
Spacious and Airy Apartment for Big Groups!
0.4 mi from Uptown, Chicago, United States
9.9Wonderful(22)
Free Wi-Fi
$386+
Check availability
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh - Chicago
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh
0.3 mi from Uptown, Chicago, United States
9.9Wonderful(28)
Free Wi-Fi
Pet friendly
$172+
Check availability
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover - Chicago
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
0.1 mi from Uptown, Chicago, United States
10Wonderful(18)
$343+
Check availability
Peaceful Beachfront Loft Rooftop Gym - Chicago
Peaceful Beachfront Loft Rooftop Gym
0.3 mi from Uptown, Chicago, United States
10Wonderful(1)
Free Wi-Fi
Pet friendly
$181+
Check availability
Uptown Gem - Chicago
Uptown Gem
0.3 mi from Uptown, Chicago, United States
10Wonderful(30)
Parking
Free Wi-Fi
Pool
$339+
Check availability
Studio Apt with Laundry, Near Shops! - Montrose Studio rep - Chicago
Studio Apt with Laundry, Near Shops! - Montrose Studio rep
0.3 mi from Uptown, Chicago, United States
7.9Good(6)
Pet friendly
$128+
Check availability
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym - Chicago
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym
0.3 mi from Uptown, Chicago, United States
8.2Very good(8)
Free Wi-Fi
Pet friendly
$158+
Check availability
Cozy Studio Apt with In-Unit Laundry and Wi-Fi! - Montrose 111 - Chicago
Cozy Studio Apt with In-Unit Laundry and Wi-Fi! - Montrose 111
0.3 mi from Uptown, Chicago, United States
8.4Very good(7)
Free Wi-Fi
Pet friendly
$186+
Check availability
City Charm Studio Apt close to Shops - Ashland 04 - Chicago
City Charm Studio Apt close to Shops - Ashland 04
0.9 mi from Uptown, Chicago, United States
Free Wi-Fi
Pet friendly
$219+
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 March, with average rates of $128. In comparison, August is the most expensive month, with prices at $525.

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

Monday offers the lowest rates in Uptown, with an average nightly price of $196. The highest prices are found on Wednesday, with average rates at $656.
Find deals

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)

March
August
$356
$415
Cheapest month to stay with an average 65% drop in price.
Most expensive month to stay with an average 45% 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 March and April.
  • 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 Monday. On the other hand, the most expensive day for hotel bookings is Wednesday.
  • 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 $229, while the most expensive was $422.
  • 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, The Bright Retreat in Andersonville, and Artistic Loft Rooftop Uptown Montrose Beach Gymwfh 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

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