Uptown holiday lettings

We found 1,951 holiday rentals — enter your dates for availability
Discover a selection of 28 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:6 Nov - 13 Nov

Interior
Terrace/patio
Living area
Living area
Wonderful
(12 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
£8,395
for 7 nights, 1 apartment
£1,199 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
French Bistro and Wine Bar - right downstairs
River North Luxury Living
Outdoors at night
The building
Exceptional
(103 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
£2,468
for 7 nights, 1 apartment
£353 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Interior
Interior
Terrace/patio
Private kitchen
Exceptional
(6 reviews)

EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath

Evanston

7% off
£7,090
for 7 nights, 1 home
£1,013 per night
includes taxes & fees
EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath
Interior
Interior
Living area
Private kitchen
Exceptional
(54 reviews)

Modern Logan Square Luxury: 5 bedroom - sleeps 16!

Chicago

7% off
£4,832
for 7 nights, 1 home
£690 per night
includes taxes & fees
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Interior
Dining
Interior
Private kitchen
Exceptional
(5 reviews)

5BR/4BA Modern SFH Logan Square!

Chicago

7% off
£2,666
for 7 nights, 1 home
£381 per night
includes taxes & fees
5BR/4BA Modern SFH Logan Square!
Dining
Living area
Living area
Terrace/patio
Exceptional
(55 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
£2,232
for 7 nights, 1 apartment
£319 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Living room area opens into dining room & kitchen
3 bedroom unit is top floor of historic greystone
Dining room area
View of Robey Hotel from back deck
Exceptional
(95 reviews)

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

Chicago

7% off
£3,426
for 7 nights, 1 home
£489 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Dining
Interior
Living area
Interior
Exceptional
(37 reviews)

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

Chicago

7% off
£4,867
for 7 nights, 1 home
£695 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Interior
Interior
Private kitchen
Room
Exceptional
(10 reviews)

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

Chicago

7% off
£1,631
for 7 nights, 1 apartment
£233 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Interior
Interior
Room
Private kitchen
Exceptional
(12 reviews)

Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!

Chicago

11% off
£4,667
for 7 nights, 1 villa
£667 per night
includes taxes & fees
Spacious 8 BDR + 2 Kitchens + Garage! Sleeps 16!
Kitchen (upstairs)
Downstairs living area
Downstairs living room
Upstairs queen bedroom 2
Exceptional
(97 reviews)

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

Chicago

7% off
£6,890
for 7 nights, 1 apartment
£984 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Doorman building with grand lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Craft cocktail bar in lobby
Heritage Outpost cafe in lobby
Exceptional
(14 reviews)

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

Chicago

7% off
£1,499
for 7 nights, 1 apartment
£214 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Interior
Living area
Private kitchen
Living area
Exceptional
(12 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

25% off
£3,009
for 7 nights, 1 apartment
£430 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Interior
Private kitchen
Interior
Interior
Wonderful
(49 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

7% off
£3,673
for 7 nights, 1 home
£525 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Dining
Exterior detail
Living area
Private kitchen
Exceptional
(64 reviews)

Wicker Park by Downtown and the Salt Shed Last Minute Deal 155.00 August 9-14

Chicago

7% off
£1,481
for 7 nights, 1 apartment
£212 per night
includes taxes & fees
Wicker Park by Downtown and the Salt Shed Last Minute Deal 155.00 August 9-14
Private kitchen
Neighborhood Photo
Interior
Private Patio
Exceptional
(35 reviews)

Cozy 2-Bedroom Apartment | Close to Wrigley

Chicago

9% off
£1,716
for 7 nights, 1 apartment
£245 per night
includes taxes & fees
Cozy 2-Bedroom Apartment | Close to Wrigley
Exterior
Interior
Dining
Living area
Exceptional
(11 reviews)

Spacious Duplex - 4BD/3BA - Sleeps 12!

Chicago

7% off
£2,823
for 7 nights, 1 apartment
£403 per night
includes taxes & fees
Spacious Duplex - 4BD/3BA - Sleeps 12!
Property grounds
Living area
Room
Private kitchen
Exceptional
(36 reviews)

Great Evanston Home- great for traveling families! Parking Included

Evanston

16% off
£2,329
for 7 nights, 1 apartment
£333 per night
includes taxes & fees
Great Evanston Home- great for traveling families! Parking Included
Private kitchen
Exterior
Interior
Dining
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
£4,852
for 7 nights, 1 apartment
£693 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Interior
Room
Private kitchen
Living area
Exceptional
(63 reviews)

EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!

Chicago

10% off
£2,458
for 7 nights, 1 apartment
£351 per night
includes taxes & fees
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Private kitchen
Property grounds
Exterior
Living area
Exceptional
(91 reviews)

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Chicago

7% off
£1,493
for 7 nights, 1 apartment
£213 per night
includes taxes & fees
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Interior
Living area
Kitchen
Room
Exceptional
(21 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
£1,360
for 7 nights, 1 apartment
£194 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Outdoor dining
Exterior detail
Interior
Room
Exceptional
(37 reviews)

Stylish Two Bedroom - A block from Wrigley Field

Chicago

7% off
£1,459
for 7 nights, 1 apartment
£208 per night
includes taxes & fees
Stylish Two Bedroom - A block from Wrigley Field
Exterior
Living area
Private kitchen
Room
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
£2,424
for 7 nights, 1 apartment
£346 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
  • 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, pools, gardens and more
  • More for less

    More 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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