Hotels in Uptown, Chicago

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Recommended by KAYAK

Best hotels in Uptown (Chicago)

Most recommended Uptown hotels

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The Guesthouse Hotel - Chicago - Balcony
The Guesthouse Hotel
Uptown
9.5Wonderful(217)
Free Wi-Fi
Pet friendly
$408+
Check availability
Spacious and Airy Apartment for Big Groups! - Chicago - Living room
Spacious and Airy Apartment for Big Groups!
Uptown
Free Wi-Fi
Pet friendly
$339+
Check availability
Great Location-Beautiful Friendly Andersonville Neighborhood - Chicago - Living room
Great Location-Beautiful Friendly Andersonville Neighborhood
Uptown
Free Wi-Fi
$272+
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Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-383 - Chicago - Lounge
Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-383
Uptown
Free Wi-Fi
Pet friendly
$175+
Check availability
Elegant Stylish Loft Oasis Uptown Rooftop Wfh Gym - Chicago - Balcony
Elegant Stylish Loft Oasis Uptown Rooftop Wfh Gym
Uptown
Free Wi-Fi
Pet friendly
$205+
Check availability
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking - Chicago - Patio
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Uptown
Free Wi-Fi
Pool
Spa
$247+
Check availability
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover - Chicago - Living room
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Uptown
$166+
Check availability
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym - Chicago - Balcony
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym
Uptown
Free Wi-Fi
Pet friendly
$200+
Check availability
Cheerful & Bright Sheridan Park Studio - Chicago
Cheerful & Bright Sheridan Park Studio
Uptown
$191+
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Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-380 - Chicago
Uptown 1BR w Gym Rooftop Pool 2 blocks to L CHI-380
Uptown
Free Wi-Fi
Pet friendly
$127+
Check availability
Andersonville / Spacious 3b / 3b / 2 decks. Cozy Bohemian Vibe. 99 Walk Score - Chicago
Andersonville / Spacious 3b / 3b / 2 decks. Cozy Bohemian Vibe. 99 Walk Score
Uptown
Free Wi-Fi
Pet friendly
$624+
Check availability
Loftium | Chic & Spacious 2 Bedroom Suite In Wrigleyville! - Chicago
Loftium | Chic & Spacious 2 Bedroom Suite In Wrigleyville!
Uptown
Free Wi-Fi
$236+
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2BR in Andersonville-Walk to train, beach, shops and restaurants! - Chicago
2BR in Andersonville-Walk to train, beach, shops and restaurants!
Uptown
Free Wi-Fi
$289+
Check availability
️Sleeps 18/Sanitized/Fast WiFi/93 Walk Score/Comfy beds/Getaway/Free Parking️ - Chicago
️Sleeps 18/Sanitized/Fast WiFi/93 Walk Score/Comfy beds/Getaway/Free Parking️
Uptown
Free Wi-Fi
$615+
Check availability
Modern Uptown 1 Br - Clean & Close To Train! Special Long Term Reservation Disc - Chicago
Modern Uptown 1 Br - Clean & Close To Train! Special Long Term Reservation Disc
Uptown
$147+
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Studio Apt with Laundry, Near Shops! - Montrose 316 & 318 - Chicago
Studio Apt with Laundry, Near Shops! - Montrose 316 & 318
Uptown
7.9Good(6)
Free Wi-Fi
Pet friendly
$128+
Check availability
3BR w/ Elevator, Patio & Laundry near the Red Line by AllSet Turnover - Chicago
3BR w/ Elevator, Patio & Laundry near the Red Line by AllSet Turnover
Uptown
$502+
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Sunny Modern Loft Montrose Beach Rooftop Wfh Gym - Chicago
Sunny Modern Loft Montrose Beach Rooftop Wfh Gym
Uptown
Free Wi-Fi
Pet friendly
$204+
Check availability
Pristine & Comfy 1br Apartment - Chicago
Pristine & Comfy 1br Apartment
Uptown
Pet friendly
$641+
Check availability
Lowest Rates! Spacious Duplex with Free Parking! - Chicago
Lowest Rates! Spacious Duplex with Free Parking!
Uptown
Pet friendly
$329+
Check availability
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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 April, with average rates of $205. In comparison, July is the most expensive month, with prices at $718.

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

Tuesday offers the lowest rates in Uptown, with an average nightly price of $152. The highest prices are found on Friday, with average rates at $575.
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How much is a Uptown hotel?

Here are our most popular & best value hotels

Good to know

Low season

April

High season

July

Average price (weeknight)

$246

Average price (weekend night)

$438
Cheapest month to stay with an average 49% drop in price.
Most expensive month to stay with an average 77% 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 April and January.
  • 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 Tuesday. On the other hand, the most expensive day for hotel bookings is Friday.
  • 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 Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover 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

Uptown hotel deals. Search for hotels in Uptown. Find cheap hotel rooms in Uptown. KAYAK searches hundreds of travel sites to help you find cheap hotels and book the room that suits you best.

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