Uptown holiday rentals

We found 1,946 holiday rentals — enter your dates for availability
Discover a selection of 31 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:18 Dec - 25 Dec

Terrace/patio
Interior
Living area
Exterior
Exceptional
(39 reviews)

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Chicago

8% off
AU$34,954
for 7 nights, 1 home
AU$4,993 per night
includes taxes & fees
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Interior
Our downtown Townhouse is in an amazing location
Room
It is huge! With lots of areas for relaxing and entertaining
Exceptional
(91 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
AU$10,918
for 7 nights, 1 home
AU$1,560 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
Private kitchen
Dining
Exterior
Interior
Exceptional
(8 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
AU$5,146
for 7 nights, 1 home
AU$735 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Dining Area
Top floor kitchen and dining area
2 spots come with the unit- occupied by the van and SUV in this photo.
Bedroom 3 w/ Queen Bed
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
AU$10,066
for 7 nights, 1 apartment
AU$1,438 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Living Room with 60 in Smart TV
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
AU$10,725
for 7 nights, 1 home
AU$1,532 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Exterior
Living area
Dining
Private kitchen
Exceptional
(112 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
AU$7,619
for 7 nights, 1 home
AU$1,088 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
View of Robey Hotel from back deck
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
Dining room area
Exceptional
(100 reviews)

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

Chicago

7% off
AU$6,363
for 7 nights, 1 home
AU$909 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Room
Interior
Interior
Living area
Exceptional
(38 reviews)

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

Chicago

7% off
AU$10,525
for 7 nights, 1 home
AU$1,504 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Terrace/patio
Living area
Living area
Private kitchen
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$4,232
for 7 nights, 1 apartment
AU$605 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Kitchen (upstairs)
Downstairs living area
Downstairs living room
Upstairs queen bedroom 2
Exceptional
(99 reviews)

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

Chicago

7% off
AU$12,397
for 7 nights, 1 apartment
AU$1,771 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Room
Interior
Private kitchen
Interior
Exceptional
(12 reviews)

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

Chicago

7% off
AU$2,994
for 7 nights, 1 apartment
AU$428 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Games room
Living area
Room
Lobby
Exceptional
(9 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

7% off
AU$10,317
for 7 nights, 1 apartment
AU$1,474 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Dining
Exterior
Interior
Room
Exceptional
(35 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,704
for 7 nights, 1 apartment
AU$1,243 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Doorman building with grand lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Craft cocktail bar in lobby
Rooftop lounge leads to roof deck with 360 degree skyline views
Exceptional
(15 reviews)

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

Chicago

7% off
AU$2,336
for 7 nights, 1 apartment
AU$334 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Living area
Belmont Harbor
Exterior
Private kitchen
Exceptional
(192 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

15% off
AU$6,707
for 7 nights, 1 home
AU$958 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Room
Dining
Private kitchen
Interior
Exceptional
(19 reviews)

Lovely 3 Bedroom condo near Wrigley!

Chicago

11% off
AU$5,745
for 7 nights, 1 apartment
AU$821 per night
includes taxes & fees
Lovely 3 Bedroom condo near Wrigley!
Living area
Exterior detail
Dining
Private kitchen
Exceptional
(71 reviews)

Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 21-23

Chicago

7% off
AU$2,601
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
Wicker Park near Downtown and the Salt Shed Special 125.00 Sept 21-23
Interior
Neighborhood Photo
Room
Private kitchen
Exceptional
(38 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

8% off
AU$3,282
for 7 nights, 1 apartment
AU$469 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Room
Interior
Interior
Private kitchen
Exceptional
(22 reviews)

Modern 2BR Near Loyola & Lake Michigan

Chicago

7% off
AU$2,446
for 7 nights, 1 apartment
AU$349 per night
includes taxes & fees
Modern 2BR Near Loyola & Lake Michigan
Living area
Room
Exterior
Interior
Exceptional
(6 reviews)

Peaceful Zen Flat | 2BR Oasis with Free Parking

Chicago

8% off
AU$3,518
for 7 nights, 1 apartment
AU$503 per night
includes taxes & fees
Peaceful Zen Flat | 2BR Oasis with Free Parking
Room
Interior
Private kitchen
Living area
Exceptional
(21 reviews)

Chicago Bear Den

Chicago

7% off
AU$2,447
for 7 nights, 1 apartment
AU$350 per night
includes taxes & fees
Chicago Bear Den
Living area
Interior
Interior
Room
Very good
(21 reviews)

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

Chicago

7% off
AU$2,153
for 7 nights, 1 apartment
AU$308 per night
includes taxes & fees
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Relax on the spacious balcony overlooking our quiet residential street.
Your home away from home in a beautiful garden setting
Kitchen with expandable eat-in dining
Loyola University 2 blocks
Exceptional
(263 reviews)

Remodeled, spacious and bright apartment — near Loyola, beach & subway

Chicago

7% off
AU$3,760
for 7 nights, 1 apartment
AU$537 per night
includes taxes & fees
Remodeled, spacious and bright apartment — near Loyola, beach & subway
Dining
Living area
Interior
Room
Exceptional
(10 reviews)

3BR Art Deco retreat with garage.

Chicago

7% off
AU$9,625
for 7 nights, 1 apartment
AU$1,375 per night
includes taxes & fees
3BR Art Deco retreat with garage.
  • 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

When is the best time to visit Uptown for a holiday rental?
The peak season for holiday rentals in Uptown typically spans from July to September, when visitors flock to the area to enjoy warm summer days and a vibrant local scene. This is an excellent time for those eager to explore the parks, indulge in outdoor dining, and participate in various local festivals that celebrate the community's cultural richness.July stands out as the most popular month, offering a lively option filled with events and activities. With average temperatures ranging from 20 to 30 degrees Celsius, it's great for leisurely strolls along the waterfront or enjoying a picnic in one of Uptown's picturesque parks.If you're looking for a more budget-friendly option, consider visiting in December. During this time, this month offers a unique charm with festive decorations and a chance to experience the local holiday spirit. Plus, you'll enjoy the beauty of Uptown without the bustling crowds.Ultimately, the best time to visit Uptown for a holiday rental depends on whether you're drawn to the energetic summer vibe or the more relaxed winter atmosphere.
What are the top attractions in Uptown, Illinois, United States of America?
Uptown, Illinois, offers a variety of attractions that reflect its rich cultural and historical significance. One of the standout features of the neighbourhood is the historic Uptown Theatre, an iconic venue that has played host to countless performances and films since its opening in 1925. Nearby, the beautiful Montrose Beach provides a scenic spot for relaxation and recreation, great for enjoying lake views and outdoor activities.The area is also known for its vibrant music scene, with venues like the Aragon Ballroom showcasing everything from concerts to dance events. For a taste of local culture, the nearby Green Mill Cocktail Lounge, a historic jazz club, offers live music and a glimpse into the city's jazz history.Additionally, the neighbourhood is home to several parks, including the expansive Montrose Point Bird Sanctuary, which attracts birdwatchers and nature lovers alike.
Are all fees included in the Uptown holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Uptown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Uptown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Uptown holiday homes?
You can find great discounts on holiday homes in Uptown on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Uptown holiday home booking on Stayz?
To find Uptown holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Uptown?
A long-stay holiday home in Uptown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Uptown holiday home?
Book your Uptown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Uptown?
Prices for holiday homes in Uptown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Uptown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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