Uptown holiday rentals

We found 1,938 holiday rentals — enter your dates for availability
Discover a selection of 29 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

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

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
S$13,827
for 7 nights, 1 apartment
S$1,975 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

8% off
S$8,903
for 7 nights, 1 home
S$1,272 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$5,071
for 7 nights, 1 home
S$724 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Dining
Interior
Interior
Living area
Exceptional
(5 reviews)

Massive Queen Anne Mansion for your whole family to stay!

Chicago

7% off
S$13,312
for 7 nights, 1 home
S$1,902 per night
includes taxes & fees
Massive Queen Anne Mansion for your whole family to stay!
Living area
Living area
Dining
Terrace/patio
Exceptional
(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
S$3,756
for 7 nights, 1 apartment
S$537 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Exterior detail
Private kitchen
Dining
Living area
Exceptional
(63 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off
S$4,285
for 7 nights, 1 apartment
S$612 per night
includes taxes & fees
Steps from the “L” train to Wrigley & Downtown
Living area
Interior
Dining
Room
Exceptional
(38 reviews)

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

Chicago

7% off
S$11,457
for 7 nights, 1 home
S$1,637 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Dining room area
3 bedroom unit is top floor of historic greystone
View of Robey Hotel from back deck
Living room area
Exceptional
(96 reviews)

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

Chicago

7% off
S$5,896
for 7 nights, 1 home
S$842 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Interior
Interior
Room
Living area
Exceptional
(12 reviews)

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

Chicago

7% off
S$2,759
for 7 nights, 1 apartment
S$394 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Kitchen (upstairs)
Downstairs living area
Upstairs queen bedroom 2
Downstairs living room
Exceptional
(98 reviews)

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

Chicago

7% off
S$12,246
for 7 nights, 1 apartment
S$1,749 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Doorman building with grand lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Heritage Outpost cafe in lobby
Rooftop lounge leads to roof deck with 360 degree skyline views
Exceptional
(14 reviews)

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

Chicago

7% off
S$2,743
for 7 nights, 1 apartment
S$392 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Dining
Private kitchen
Interior
Interior
Wonderful
(49 reviews)

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

Chicago

8% off
S$6,780
for 7 nights, 1 home
S$969 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Interior
Neighborhood Photo
Room
Private Patio
Exceptional
(35 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

9% off
S$4,128
for 7 nights, 1 apartment
S$590 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Room
Exterior detail
Dining
Private kitchen
Exceptional
(69 reviews)

Wicker Park near Downtown and the Salt Shed August Special 129.00 per night

Chicago

7% off
S$2,797
for 7 nights, 1 apartment
S$400 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed August Special 129.00 per night
Interior
Exterior
Private kitchen
Dining
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
S$7,882
for 7 nights, 1 apartment
S$1,126 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Interior
Room
Living area
Living area
Exceptional
(63 reviews)

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

Chicago

10% off
S$4,684
for 7 nights, 1 apartment
S$669 per night
includes taxes & fees
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Room
Living area
Interior
Kitchen
Exceptional
(25 reviews)

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

Chicago

7% off
S$2,489
for 7 nights, 1 apartment
S$356 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Living area
Kitchen
Kitchen
Room
Exceptional
(12 reviews)

Large 2-Bedroom w/ Huge Roofdeck view of Skyline

Chicago

8% off
S$2,672
for 7 nights, 1 apartment
S$382 per night
includes taxes & fees
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Private kitchen
Interior
Bathroom
Room
Exceptional
(20 reviews)

Chicago Bear Den

Chicago

7% off
S$2,239
for 7 nights, 1 apartment
S$320 per night
includes taxes & fees
Chicago Bear Den
Living area
Private kitchen
Room
Children’s area
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
S$3,808
for 7 nights, 1 apartment
S$544 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
Exterior
Interior
Living area
Room
Very good
(21 reviews)

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

Chicago

7% off
S$2,119
for 7 nights, 1 apartment
S$303 per night
includes taxes & fees
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Private kitchen
Living area
Interior
Dining
Wonderful
(147 reviews)

Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

Chicago

7% off
S$2,805
for 7 nights, 1 apartment
S$401 per night
includes taxes & fees
Walk to Wrigley/ Boystown -Chicago 3BR/2Ba Duplex-paid parking available!

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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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