Uptown holiday lettings
We found 1,974 holiday rentals — enter your dates for availability
Discover a selection of 35 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:1 Jan - 8 Jan
Exceptional
(92 reviews)
Historic luxury townhouse on Chicago's Gold Coast
Chicago
£5,399
for 7 nights, 1 home
£771 per night
includes taxes & fees
Exceptional
(6 reviews)
EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath
Evanston
£7,097
for 7 nights, 1 home
£1,014 per night
includes taxes & fees
Exceptional
(106 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago
£2,914
for 7 nights, 1 apartment
£416 per night
includes taxes & fees
Exceptional
(100 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
£7,842
for 7 nights, 1 apartment
£1,120 per night
includes taxes & fees
Exceptional
(54 reviews)
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Chicago
£3,991
for 7 nights, 1 home
£570 per night
includes taxes & fees
Exceptional
(315 reviews)
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Chicago
£1,506
for 7 nights, 1 apartment
£215 per night
includes taxes & fees
Exceptional
(92 reviews)
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Chicago
£5,268
for 7 nights, 1 home
£753 per night
includes taxes & fees
Exceptional
(69 reviews)
Steps from the “L” train to Wrigley & Downtown
Chicago
£2,539
for 7 nights, 1 apartment
£363 per night
includes taxes & fees
Exceptional
(14 reviews)
Wicker Park: Cozy Fireplace, Grand Piano
Chicago
£3,022
for 7 nights, 1 apartment
£432 per night
includes taxes & fees
Wonderful
(50 reviews)
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Chicago
£2,974
for 7 nights, 1 home
£425 per night
includes taxes & fees
Exceptional
(7 reviews)
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Chicago
£5,959
for 7 nights, 1 apartment
£851 per night
includes taxes & fees
Exceptional
(10 reviews)
Elite 4BR Art Deco suite. Garage included.
Chicago
£5,085
for 7 nights, 1 apartment
£726 per night
includes taxes & fees
Exceptional
(75 reviews)
Private Historic Coach House Wicker Park
Chicago
£1,832
for 7 nights, 1 home
£262 per night
includes taxes & fees
Exceptional
(193 reviews)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago
£3,062
for 7 nights, 1 home
£437 per night
includes taxes & fees
Exceptional
(37 reviews)
Lincoln Park Charm Near Everything + On site Parking Spot Included
Chicago
£4,259
for 7 nights, 1 apartment
£608 per night
includes taxes & fees
Exceptional
(109 reviews)
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Chicago
£1,366
for 7 nights, 1 apartment
£195 per night
includes taxes & fees
Exceptional
(101 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
£4,652
for 7 nights, 1 home
£665 per night
includes taxes & fees
Exceptional
(114 reviews)
Wrigley Field/Lakeview -Entire Home- Large Groups!
Chicago
£4,220
for 7 nights, 1 home
£603 per night
includes taxes & fees
Exceptional
(373 reviews)
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Chicago
£1,124
for 7 nights, 1 apartment
£161 per night
includes taxes & fees
Exceptional
(38 reviews)
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Chicago
£4,480
for 7 nights, 1 home
£640 per night
includes taxes & fees
Exceptional
(63 reviews)
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Chicago
£2,500
for 7 nights, 1 apartment
£357 per night
includes taxes & fees
Exceptional
(32 reviews)
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Chicago
£1,215
for 7 nights, 1 apartment
£174 per night
includes taxes & fees
Exceptional
(22 reviews)
Chicago Bear Den
Chicago
£1,237
for 7 nights, 1 apartment
£177 per night
includes taxes & fees
Exceptional
(30 reviews)
2BD/1 BA with summer patio in quiet Roscoe Village
Chicago
£1,118
for 7 nights, 1 apartment
£160 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
Wrigleyville Suites
Sleeps 10 · 3 bedrooms
Relaxing Chicago Studio
Sleeps 4 · 1 bathroom
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Sleeps 4 · 2 bedrooms · 1 bathroom
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Sleeps 2 · 1 bedroom · 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
Top rated rentals - Uptown
Great option!!!!
We had a lovely stay! Amenities were next level! Lots in area to access as well! Perfect in every regard!
Kara
Stayed Aug 2024
An amazing place from which to explore Chicago
Had an amazing stay, the Sentral staff, all the staff, were so friendly and welcoming. For example, Augustine sorted out an issue with a missing fob so very quickly and easily.
The property itself is amazing. We went for one of the upgraded apartments and were lucky enough to get one on the 18th floor with views covering the city and the park (so we could look one way and see the Willis Tower in one direction and the lake and Museum district in the other. The sunrises over the lake were particularly spectacular. The apartment was fitted out exactly as the online walk though tour shows it and it was a pleasure to come back to after exploring the city each day. The shared facilities on the 7th floor were great - we only really used the Winter garden and the out door hot tub - from which you can also watch the sunrise.
Being in the South loop and right on the edge of the park district it is really well positioned to act as a base to explore Chicago - there was a Divvy bike rack (where you can rent bikes to explore the area - with many more dotted around so you can stop / start easily) within a couple hundred meters of the apartment block. With it being within walking distance of all the CityPass attractions (which lets you visit Chicago places of interest at a significant saving) it was perfect.
Richard
Stayed Nov 2022
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.
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