A frozen river with a city skyline in the background.

Uptown holiday rentals

We found 1,926 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:27 Nov - 4 Dec

Exceptional

(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off

S$11,198

for 7 nights, 1 apartment

S$1,600 per night

includes taxes & fees

Exceptional

(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

8% off

S$8,566

for 7 nights, 1 home

S$1,224 per night

includes taxes & fees

Exceptional

(5 reviews)

Massive Queen Anne Mansion for your whole family to stay!

Chicago

7% off

S$12,900

for 7 nights, 1 home

S$1,843 per night

includes taxes & fees

Exceptional

(7 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off

S$4,312

for 7 nights, 1 home

S$616 per night

includes taxes & fees

Exceptional

(56 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off

S$3,808

for 7 nights, 1 apartment

S$544 per night

includes taxes & fees

Living room area opens into dining room & kitchen

3 bedroom unit is top floor of historic greystone

Exceptional

(97 reviews)

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

Chicago

7% off

S$5,906

for 7 nights, 1 home

S$844 per night

includes taxes & fees

Wonderful

(49 reviews)

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

Chicago

7% off

S$5,723

for 7 nights, 1 home

S$818 per night

includes taxes & fees

Exceptional

(38 reviews)

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

Chicago

7% off

S$6,674

for 7 nights, 1 home

S$953 per night

includes taxes & fees

Exceptional

(63 reviews)

Steps from the “L” train to Wrigley & Downtown

Chicago

7% off

S$4,292

for 7 nights, 1 apartment

S$613 per night

includes taxes & fees

Exceptional

(98 reviews)

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

Chicago

7% off

S$11,864

for 7 nights, 1 apartment

S$1,695 per night

includes taxes & fees

Exceptional

(69 reviews)

Wicker Park near Downtown and the Salt Shed Labor Day Special 229.00 Sept 5-7

Chicago

7% off

S$2,070

for 7 nights, 1 apartment

S$296 per night

includes taxes & fees

Exceptional

(36 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

8% off

S$2,455

for 7 nights, 1 apartment

S$351 per night

includes taxes & fees

Exceptional

(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off

S$7,465

for 7 nights, 1 apartment

S$1,066 per night

includes taxes & fees

Exceptional

(26 reviews)

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

Chicago

7% off

S$2,262

for 7 nights, 1 apartment

S$323 per night

includes taxes & fees

Exceptional

(14 reviews)

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

Chicago

7% off

S$4,045

for 7 nights, 1 apartment

S$578 per night

includes taxes & fees

Exceptional

(20 reviews)

Chicago Bear Den

Chicago

7% off

S$2,243

for 7 nights, 1 apartment

S$320 per night

includes taxes & fees

Very good

(21 reviews)

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

Chicago

7% off

S$2,054

for 7 nights, 1 apartment

S$293 per night

includes taxes & fees

Exceptional

(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off

S$2,800

for 7 nights, 1 apartment

S$400 per night

includes taxes & fees

Wonderful

(147 reviews)

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

Chicago

7% off

S$2,810

for 7 nights, 1 apartment

S$401 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find properties near top attractions in Uptown

A historic theater with ornate architecture and a prominent marquee.

Aragon Ballroom

Montrose Beach

A marina with various sailboats and yachts docked.

Montrose Harbor

A city street with a bus stop, trees, and buildings.

Hutchinson Street Historic District

A pyramid-shaped monument with a green door, a statue of a woman, and a lion statue.

Graceland Cemetery

Find the best place to stay - Uptown

Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover

Sleeps 4 · 2 bedrooms · 1 bathroom

Wrigleyville Suites

Sleeps 10 · 3 bedrooms

Premier Host

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

Relaxing Chicago Studio

Sleeps 4 · 1 bathroom

Premier Host

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Sleeps 2 · 1 bedroom · 1 bathroom

Walk to Wrigley! Spacious 3BR in the Heart of Chicago

Sleeps 6 · 3 bedrooms · 1 bathroom

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.

More holiday ideas

Holiday homes