Uptown holiday homes

We found 2,029 holiday rentals — enter your dates for availability

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May 2025

June 2025

Discover a selection of 7 homes 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:15 Aug - 22 Aug

Live the local life in your Kasa's living room

Exceptional

(37 reviews)

Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago

Chicago, Illinois

8% off

NZ$1,152 per night

includes taxes & fees

All of our units are one-of-a-kind; decor may vary from the photos shown

Exceptional

(10 reviews)

#1514 - Kasa Magnificent Mile Chicago

Chicago, Illinois

8% off

NZ$467 per night

includes taxes & fees

Arrive to a freshly made bed and nice fluffy pillows

Exceptional

(16 reviews)

#1613 - Kasa Magnificent Mile Chicago

Chicago, Illinois

8% off

NZ$569 per night

includes taxes & fees

Exceptional

(8 reviews)

3BR Luxury Modern Apartment

Chicago, Illinois

7% off

NZ$1,043 per night

includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(226 reviews)

Spectacular Corner 2BR Penthouse in the Loop | Roof Deck

Chicago, Illinois

7% off

NZ$954 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(33 reviews)

Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

NZ$859 per night

includes taxes & fees

Wake up to nice natural light though the large windows

Exceptional

(14 reviews)

Kasa | Family Friendly 3 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$1,494 per night

includes taxes & fees

Exceptional

(20 reviews)

Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago

Chicago, Illinois

8% off

NZ$1,494 per night

includes taxes & fees

Our apartments have a 4.87 rating across all booking channels for 180,000+ nights hosted, and counting

Exceptional

(9 reviews)

Kasa | Inviting 1 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$765 per night

includes taxes & fees

Your Kasa experience begins before arrival: we send check-in instructions via email

Exceptional

(12 reviews)

Kasa | Relaxing 1 BD + Near Local Eateries | Chicago

Chicago, Illinois

8% off

NZ$570 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Find properties near top attractions in Uptown

Lincoln Park

Montrose Beach

Montrose Harbor

Hutchinson Street Historic District

Find the best place to stay - Uptown

Showing deals for: 15 Aug - 18 Aug

Furniture,Indoors,Living Room,Home Decor,Couch

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

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 apartment

NZ$766 per night

includes taxes & fees

Living Area- Pullout Couch has a Queen Size Memory Foam Mattress

The Bright Retreat in Andersonville

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

NZ$619 per night

includes taxes & fees

Home Decor,Furniture,Indoors,Living Room,Table

Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

Sleeps 6 · 2 bedrooms · 1 bathroom

for 3 nights, 1 apartment

NZ$776 per night

includes taxes & fees

Living Room with a view, and balcony door

Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

NZ$1,009 per night

includes taxes & fees

3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 room

NZ$1,558 per night

includes taxes & fees

Luxurious 3 Bedroom Apartment in Chicago

Sleeps 5 · 3 bedrooms · 1 bathroom

for 3 nights, 1 apartment

NZ$624 per night

includes taxes & fees

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
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 home accommodation in Uptown?

Apartments are the most popular style of holiday home in Uptown, according to our data. Even if you’ve got something a little different in mind, Bookabach 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 home 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 Bookabach holiday homes 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 Bookabach and the number of guests to see your home 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 homes 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 homes and find the pawfect pad on Bookabach.

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 Bookabach. 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 home amenities in Uptown?

A garden, a nearby waterfront and a lake view top the list of most popular home amenities in Uptown. Whether you plan to travel solo, with your significant other or a group of family members, Bookabach will help you find a holiday home that suits your tastes with all the features you’re looking for.

Are there large group holiday homes 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, Bookabach can help you find a large group home that fits the occasion.

Are there holiday homes 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 homes in Uptown?

Uptown has nine one-bedroom homes on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom holiday home 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 homes 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 homes with WiFi in Uptown?

You’ll have a choice of 10 holiday homes 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 Bookabach.

How can I find holiday homes with air conditioning in Uptown?

Pick your travel dates and then make use of the filters to find holiday homes with air conditioning in Uptown on Bookabach. 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 home in Uptown?

The minimum required age is usually 16, 18 or 21. It can change across properties on Bookabach, so look at the rules of your chosen Uptown stay before making a booking.

How long can I rent a holiday home 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.