Uptown holiday rentals
We found 1,950 holiday rentals — enter your dates for availability
Discover a selection of 32 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

Exceptional
(39 reviews)
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Chicago
AU$35,540
for 7 nights, 1 home
AU$5,077 per night
includes taxes & fees

Exceptional
(91 reviews)
Historic luxury townhouse on Chicago's Gold Coast
Chicago
AU$10,632
for 7 nights, 1 home
AU$1,519 per night
includes taxes & fees

Exceptional
(34 reviews)
The Exclusive- 7 Bed, 6 Bath Retreat
Chicago
AU$10,154
for 7 nights, 1 apartment
AU$1,451 per night
includes taxes & fees

Exceptional
(8 reviews)
5BR/4BA Modern SFH Logan Square!
Chicago
AU$4,949
for 7 nights, 1 home
AU$707 per night
includes taxes & fees

Exceptional
(92 reviews)
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Chicago
AU$10,991
for 7 nights, 1 home
AU$1,570 per night
includes taxes & fees

Exceptional
(111 reviews)
Wrigley Field/Lakeview -Entire Home- Large Groups!
Chicago
AU$7,568
for 7 nights, 1 home
AU$1,081 per night
includes taxes & fees

Exceptional
(99 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
AU$6,320
for 7 nights, 1 home
AU$903 per night
includes taxes & fees

Exceptional
(38 reviews)
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Chicago
AU$10,823
for 7 nights, 1 home
AU$1,546 per night
includes taxes & fees

Exceptional
(12 reviews)
Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!
Chicago
AU$8,270
for 7 nights, 1 villa
AU$1,181 per night
includes taxes & fees

Exceptional
(57 reviews)
Cozy two bedroom close to Wrigley Field
Chicago
AU$4,204
for 7 nights, 1 apartment
AU$601 per night
includes taxes & fees

Exceptional
(99 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
AU$12,314
for 7 nights, 1 apartment
AU$1,759 per night
includes taxes & fees

Exceptional
(12 reviews)
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Chicago
AU$2,973
for 7 nights, 1 apartment
AU$425 per night
includes taxes & fees

Exceptional
(7 reviews)
Elite 4BR Art Deco suite. Garage included.
Chicago
AU$10,511
for 7 nights, 1 apartment
AU$1,502 per night
includes taxes & fees

Exceptional
(35 reviews)
Lincoln Park Charm Near Everything + On site Parking Spot Included
Chicago
AU$8,646
for 7 nights, 1 apartment
AU$1,235 per night
includes taxes & fees

Exceptional
(15 reviews)
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Chicago
AU$2,320
for 7 nights, 1 apartment
AU$331 per night
includes taxes & fees

Exceptional
(19 reviews)
Lovely 3 Bedroom condo near Wrigley!
Chicago
AU$5,706
for 7 nights, 1 apartment
AU$815 per night
includes taxes & fees

Exceptional
(71 reviews)
Wicker Park near Downtown and the Salt Shed Special 115.00 Sept 8-11
Chicago
AU$2,619
for 7 nights, 1 apartment
AU$374 per night
includes taxes & fees

Exceptional
(192 reviews)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago
AU$6,662
for 7 nights, 1 home
AU$952 per night
includes taxes & fees

Exceptional
(37 reviews)
Cozy 2-Bedroom Apartment | Close to Wrigley
Chicago
AU$3,723
for 7 nights, 1 apartment
AU$532 per night
includes taxes & fees

Exceptional
(6 reviews)
Peaceful Zen Flat | 2BR Oasis with Free Parking
Chicago
AU$3,507
for 7 nights, 1 apartment
AU$501 per night
includes taxes & fees

Exceptional
(21 reviews)
Chicago Bear Den
Chicago
AU$2,431
for 7 nights, 1 apartment
AU$347 per night
includes taxes & fees

Very good
(21 reviews)
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Chicago
AU$2,138
for 7 nights, 1 apartment
AU$305 per night
includes taxes & fees

Exceptional
(262 reviews)
Remodeled, spacious and bright apartment — near Loyola, beach & subway
Chicago
AU$3,606
for 7 nights, 1 apartment
AU$515 per night
includes taxes & fees

Exceptional
(9 reviews)
3BR Art Deco retreat with garage.
Chicago
AU$9,891
for 7 nights, 1 apartment
AU$1,413 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Uptown

Hutchinson Street Historic District
More information about Hutchinson Street Historic District. Opens in a new window.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

Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Sleeps 2 · 1 bedroom · 1 bathroom

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Sleeps 2 · 1 bedroom · 1 bathroom

Relaxing Chicago Studio
Sleeps 4 · 1 bathroom

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Sleeps 2 · 1 bedroom · 1 bathroom
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore 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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