Uptown holiday lettings
We found 1,950 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

Wonderful
(12 reviews)
6BD/5BTH + Roofdeck - Downtown Chicago!
Chicago
£8,311
for 7 nights, 1 apartment
£1,187 per night
includes taxes & fees

Exceptional
(54 reviews)
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Chicago
£5,663
for 7 nights, 1 home
£809 per night
includes taxes & fees

Exceptional
(7 reviews)
5BR/4BA Modern SFH Logan Square!
Chicago
£3,115
for 7 nights, 1 home
£445 per night
includes taxes & fees

Exceptional
(5 reviews)
Massive Queen Anne Mansion for your whole family to stay!
Chicago
£7,974
for 7 nights, 1 home
£1,139 per night
includes taxes & fees

Exceptional
(56 reviews)
Cozy two bedroom close to Wrigley Field
Chicago
£2,237
for 7 nights, 1 apartment
£320 per night
includes taxes & fees

Exceptional
(63 reviews)
Steps from the “L” train to Wrigley & Downtown
Chicago
£2,428
for 7 nights, 1 apartment
£347 per night
includes taxes & fees

Exceptional
(38 reviews)
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Chicago
£6,837
for 7 nights, 1 home
£977 per night
includes taxes & fees

Exceptional
(96 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
£3,391
for 7 nights, 1 home
£484 per night
includes taxes & fees

Exceptional
(11 reviews)
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Chicago
£1,613
for 7 nights, 1 apartment
£230 per night
includes taxes & fees

Exceptional
(98 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
£7,318
for 7 nights, 1 apartment
£1,045 per night
includes taxes & fees

Exceptional
(14 reviews)
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Chicago
£1,592
for 7 nights, 1 apartment
£227 per night
includes taxes & fees

Wonderful
(49 reviews)
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Chicago
£4,288
for 7 nights, 1 home
£613 per night
includes taxes & fees

Exceptional
(35 reviews)
Cozy 2-Bedroom Apartment | Close to Wrigley
Chicago
£2,433
for 7 nights, 1 apartment
£348 per night
includes taxes & fees

Exceptional
(69 reviews)
Wicker Park near Downtown and the Salt Shed August Special 129.00 per night
Chicago
£1,625
for 7 nights, 1 apartment
£232 per night
includes taxes & fees

Exceptional
(34 reviews)
Lincoln Park Charm Near Everything + On site Parking Spot Included
Chicago
£4,800
for 7 nights, 1 apartment
£686 per night
includes taxes & fees

Exceptional
(63 reviews)
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Chicago
£2,683
for 7 nights, 1 apartment
£383 per night
includes taxes & fees

Exceptional
(95 reviews)
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Chicago
£1,682
for 7 nights, 1 apartment
£240 per night
includes taxes & fees

Exceptional
(25 reviews)
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Chicago
£1,463
for 7 nights, 1 apartment
£209 per night
includes taxes & fees

Exceptional
(12 reviews)
Large 2-Bedroom w/ Huge Roofdeck view of Skyline
Chicago
£1,677
for 7 nights, 1 apartment
£240 per night
includes taxes & fees

Exceptional
(20 reviews)
Chicago Bear Den
Chicago
£1,310
for 7 nights, 1 apartment
£187 per night
includes taxes & fees

Exceptional
(6 reviews)
Peaceful Zen Flat | 2BR Oasis with Free Parking
Chicago
£2,201
for 7 nights, 1 apartment
£314 per night
includes taxes & fees

Very good
(21 reviews)
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
Chicago
£1,239
for 7 nights, 1 apartment
£177 per night
includes taxes & fees
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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 6 · 3 bedrooms

Relaxing Chicago Studio
Sleeps 4 · 1 bathroom

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

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

Massive Queen Anne Mansion for your whole family to stay!
Sleeps 15 · 6 bedrooms · 3+ bathrooms
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to rent a holiday home in Uptown?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Uptown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Uptown holiday house rentals?
You can find great discounts on house rentals in Uptown on Vrbo, 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.
Are there any Uptown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in Uptown?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a Uptown holiday rental?
Book your Uptown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Uptown home rental booking on Vrbo?
To find Uptown holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.
Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Uptown holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.
Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.
More holiday ideas
- West Ridge Holiday Rentals
- Ravenswood Holiday Rentals
- Lakeview Holiday Rentals
- Andersonville Holiday Rentals
- Old Town Triangle Holiday Rentals
- Logan Square Holiday Rentals
- Wrigley Field Holiday Rentals
- Wrigley View Rooftop Holiday Rentals
- Sheridan Park Holiday Rentals
- Loyola University Chicago Holiday Rentals
- Irving Park East Holiday Rentals
- Wicker Park Holiday Rentals
- Rogers Park Holiday Rentals
- Lincoln Square Holiday Rentals
- Edgewater Holiday Rentals
- Lake View East Holiday Rentals
- Sheffield and DePaul Holiday Rentals
- Montrose Beach Holiday Rentals
- Avondale Holiday Rentals
- Downtown Chicago Holiday Rentals
- Bucktown Holiday Rentals
- North Side Holiday Rentals
- Vic Theatre Holiday Rentals
- Lincoln Park Holiday Rentals
- Hutchinson Street Historic District Holiday Rentals
- Wrightwood Neighbors Holiday Rentals
- Lincoln Park Holiday Rentals
- Chicago Holiday Rentals
- Old Town Chicago Holiday Rentals
- Wrigleyville Holiday Rentals
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