Hotels in Uptown, Chicago

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Booking Insights
Recommended by KAYAK

Best hotels in Uptown (Chicago)

The Guesthouse Hotel - Chicago - Balcony
The Guesthouse Hotel
0.9 mi from Uptown, Chicago, United States
9.4Wonderful(231)
Free Wi-Fi
Pet friendly
$365+
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)
House
Free Wi-Fi
$332+
Check availability
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(23)
Apartment
Free Wi-Fi
$311+
Check availability
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking - Chicago - Lobby
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
0.3 mi from Uptown, Chicago, United States
9.8Wonderful(11)
Apartment
Free Wi-Fi
Pool
$288+
Check availability
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym - Chicago - Balcony
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym
0.3 mi from Uptown, Chicago, United States
8.6Very good(10)
Apartment
Free Wi-Fi
Pet friendly
$212+
Check availability
Elegant 2BR Apartment w/ In-Unit Laundry - Chicago - Bedroom
Elegant 2BR Apartment w/ In-Unit Laundry
0.2 mi from Uptown, Chicago, United States
10Wonderful(2)
Apartment
$204+
Check availability
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)
Condo
$341+
Check availability
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen - Chicago - Living room
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
0.4 mi from Uptown, Chicago, United States
9.3Wonderful(9)
Condo
$271+
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(43)
Condo
Parking
Free Wi-Fi
$205+
Check availability
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(60)
Apartment
Free Wi-Fi
$313+
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(128)
Apartment
Free Wi-Fi
$248+
Check availability
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh - Chicago - Balcony
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh
0.3 mi from Uptown, Chicago, United States
9.9Wonderful(40)
Apartment
Free Wi-Fi
Pet friendly
$210+
Check availability
Uptown Studio Gem Sum - Chicago - Bedroom
Uptown Studio Gem Sum
0.3 mi from Uptown, Chicago, United States
6.5Okay(4)
Apartment
$152+
Check availability
Sunny Studio in Heart of Ravenswood - Chicago - Kitchen
Sunny Studio in Heart of Ravenswood
0.9 mi from Uptown, Chicago, United States
9.0Wonderful(2)
Apartment
$155+
Check availability
Delightful 1BR Apt in Ravenswood - Chicago - Bedroom
Delightful 1BR Apt in Ravenswood
0.8 mi from Uptown, Chicago, United States
8.0Very good(1)
Apartment
$168+
Check availability
Uptown Gem - Chicago
Uptown Gem
0.3 mi from Uptown, Chicago, United States
9.4Wonderful(32)
Apartment
Parking
Free Wi-Fi
Pool
$252+
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(20)
Condo
$194+
Check availability
Elegant 2BR Apartment with In-Unit Laundry - Sheridan 102 - Chicago
Elegant 2BR Apartment with In-Unit Laundry - Sheridan 102
0.2 mi from Uptown, Chicago, United States
9.8Wonderful(10)
Apartment
Free Wi-Fi
Pet friendly
$217+
Check availability
Peaceful Beachfront Loft Rooftop Gym - Chicago
Peaceful Beachfront Loft Rooftop Gym
0.3 mi from Uptown, Chicago, United States
10Wonderful(1)
Apartment
Free Wi-Fi
Pet friendly
$181+
Check availability
Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway condo - Chicago
Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway condo
0.1 mi from Uptown, Chicago, United States
Apartment
Free Wi-Fi
$192+
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 December, with average rates of $183. In comparison, November is the most expensive month, with prices at $1,051.

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 $159. The highest prices are found on Wednesday, with average rates at $788.

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)

December
November
$446
$208
Cheapest month to stay with an average 53% drop in price.
Most expensive month to stay with an average 171% 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 December 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 $422, 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