Uptown holiday rentals

We found 1,944 holiday rentals — enter your dates for availability
Discover a selection of 28 apartments and other holiday rentals in Uptown that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Uptown

Showing deals for:20 Nov - 27 Nov

Interior
Terrace/patio
Living area
Private kitchen
Wonderful
(12 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
S$14,808
for 7 nights, 1 apartment
S$2,115 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Private kitchen
Interior
Living area
Interior
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

7% off
S$9,870
for 7 nights, 1 home
S$1,410 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Interior
Dining
Exterior
Interior
Exceptional
(7 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
S$5,482
for 7 nights, 1 home
S$783 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Interior
Interior
Living area
Dining
Exceptional
(5 reviews)

Massive Queen Anne Mansion for your whole family to stay!

Chicago

7% off
S$13,408
for 7 nights, 1 home
S$1,915 per night
includes taxes & fees
Massive Queen Anne Mansion for your whole family to stay!
Living area
Living area
Private kitchen
Dining
Exceptional
(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
S$3,783
for 7 nights, 1 apartment
S$540 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Living area
Interior
Dining
Room
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
S$11,726
for 7 nights, 1 home
S$1,675 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Dining room area
Living room area
Exceptional
(96 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
S$5,932
for 7 nights, 1 home
S$847 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Interior
Interior
Private kitchen
Room
Exceptional
(11 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
S$2,801
for 7 nights, 1 apartment
S$400 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior
Private kitchen
Room
Exterior
Exceptional
(34 reviews)

Soft Suede and Warm Bricks at a Stylish Rogers Park Home

Chicago

6% off
S$3,908
for 7 nights, 1 apartment
S$558 per night
includes taxes & fees
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
Kitchen (upstairs)
Downstairs living area
Fun Mirror Wall Upstairs
Downstairs living room
Exceptional
(97 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
S$12,695
for 7 nights, 1 apartment
S$1,814 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Craft cocktail bar in lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Heritage Outpost cafe in lobby
Doorman building with grand lobby
Exceptional
(14 reviews)

Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking

Chicago

7% off
S$2,763
for 7 nights, 1 apartment
S$395 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Interior
Private kitchen
Dining
Interior
Wonderful
(49 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
S$7,451
for 7 nights, 1 home
S$1,064 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Interior
Neighborhood Photo
Private Patio
Private kitchen
Exceptional
(35 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

9% off
S$4,205
for 7 nights, 1 apartment
S$601 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Dining
Exterior detail
Private kitchen
Living area
Exceptional
(69 reviews)

Wicker Park by Downtown and the Salt Shed Last Minute Deal 125.00 August 17-20

Chicago

7% off
S$2,863
for 7 nights, 1 apartment
S$409 per night
includes taxes & fees
Wicker Park by Downtown and the Salt Shed Last Minute Deal 125.00 August 17-20
Interior
Exterior
Dining
Room
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
S$8,116
for 7 nights, 1 apartment
S$1,159 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Private kitchen
Room
Living area
Interior
Exceptional
(63 reviews)

EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!

Chicago

10% off
S$4,718
for 7 nights, 1 apartment
S$674 per night
includes taxes & fees
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Living area
Property grounds
Private kitchen
Exterior
Exceptional
(95 reviews)

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Chicago

7% off
S$2,888
for 7 nights, 1 apartment
S$413 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Interior
Living area
Dining
Kitchen
Exceptional
(23 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
S$2,526
for 7 nights, 1 apartment
S$361 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Room
Kitchen
Kitchen
Living area
Exceptional
(10 reviews)

Large 2-Bedroom w/ Huge Roofdeck view of Skyline

Chicago

8% off
S$2,882
for 7 nights, 1 apartment
S$412 per night
includes taxes & fees
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Exterior
Living area
Living area
Room
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
S$4,108
for 7 nights, 1 apartment
S$587 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
Dining
Outdoor dining
Exterior detail
Room
Exceptional
(47 reviews)

Lincoln Square Oasis - Bright, Clean and in Great Location

Chicago

7% off
S$1,865
for 7 nights, 1 apartment
S$266 per night
includes taxes & fees
Lincoln Square Oasis - Bright, Clean and in Great Location
Living area
Interior
Bathroom
Room
Exceptional
(20 reviews)

Chicago Bear Den

Chicago

7% off
S$2,255
for 7 nights, 1 apartment
S$322 per night
includes taxes & fees
Chicago Bear Den
Exterior
Private kitchen
Children’s area
Room
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
S$3,927
for 7 nights, 1 apartment
S$561 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
Living area
Interior
Room
Interior
Very good
(21 reviews)

Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

Chicago

7% off
S$2,115
for 7 nights, 1 apartment
S$302 per night
includes taxes & fees
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental accommodation in Uptown?
Apartments are the most popular style of holiday rental in Uptown, according to our data. Even if you've got something a little different in mind, Vrbo has holiday homes in all sizes and shapes. Browse our options to find your perfect pad.
How much does it cost to rent a holiday rental in Uptown?
Length of stay, property type and season are among the factors that can determine the price of a holiday home. Simply add your dates of travel to find your perfect match. From comfy cabins to expansive luxury villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Uptown?
Prices for beach houses in Uptown will vary depending on the size and style of the property and when you're travelling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to refine your search by ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Uptown?
With 26 properties that welcome pets, your furry little friend can join in the fun on your Uptown getaway. Use our filter tool to search our pet-friendly holiday rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Uptown?
Tick the "pool" box in our filter tool and take your pick of two houses with private pools in Uptown on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday property comes with its own pool.
What are popular rental amenities in Uptown?
A garden, a nearby waterfront and a lake view top the list of most popular rental amenities in Uptown. Whether you plan to travel solo, with your significant other or a group of family members, Vrbo will help you find a holiday rental that suits your tastes with all the features you're looking for.
Are there large group holiday rentals in Uptown?
With three properties that can sleep 10 or more people in Uptown, there's no need to cross anyone off the invite list. From family holidays to special events like weddings and birthday parties, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals in Uptown that welcome kids?
Bring the entire family together for an adventure in Uptown at one of our 26 family-friendly holiday properties. Lots of these stays provide amenities that are perfect for getaways with youngsters, like kitchens, extra bedrooms and outdoor spaces. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Uptown?
There are lots of exciting things to see and do with the family in Uptown, such as:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday rentals in Uptown?
Uptown has nine one-bedroom rentals on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom holiday rental is ideal if you're travelling with a friend or your partner. And with home comforts like air conditioning and more privacy than a standard hotel, you'll be able to relax while enjoying this amazing destination.
Can I find two-bedroom holiday rentals in Uptown?
Pick from five two-bedroom holiday homes in Uptown. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's space for whoever's fortunate enough to be joining in on the fun.
Are there holiday rentals with WiFi in Uptown?
You'll have a choice of 10 holiday rentals with WiFi in Uptown. If you want to disconnect from daily life during your trip, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Uptown?
Pick your travel dates and then make use of the filters to find holiday rentals with air conditioning in Uptown on Vrbo. With 26 air-conditioned properties on offer here, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Uptown?
The minimum required age is usually 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Uptown stay before making a booking.
How long can I rent a holiday rental in Uptown for?
The amount of time you can rent an Uptown holiday home for depends on the property. Just put in your preferred travel dates to view available options that offer long-term stays. They come with all the things you need to make your extended trip more convenient and enjoyable, such as kitchens and yards. Some properties might also offer discounted weekly or monthly prices, so you can stay longer for less money.

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