Uptown holiday rentals
We found 1,909 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:8 Jan - 15 Jan
Exceptional
(92 reviews)
Historic luxury townhouse on Chicago's Gold Coast
Chicago
S$6,551
for 7 nights, 1 home
S$936 per night
includes taxes & fees
Exceptional
(107 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago
S$4,259
for 7 nights, 1 apartment
S$608 per night
includes taxes & fees
Exceptional
(101 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago
S$13,115
for 7 nights, 1 apartment
S$1,874 per night
includes taxes & fees
Exceptional
(54 reviews)
Modern Logan Square Luxury: 5 bedroom - sleeps 16!
Chicago
S$5,553
for 7 nights, 1 home
S$793 per night
includes taxes & fees
Exceptional
(93 reviews)
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Chicago
S$6,700
for 7 nights, 1 home
S$957 per night
includes taxes & fees
Exceptional
(69 reviews)
Steps from the “L” train to Wrigley & Downtown
Chicago
S$4,207
for 7 nights, 1 apartment
S$601 per night
includes taxes & fees
Wonderful
(50 reviews)
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Chicago
S$4,299
for 7 nights, 1 home
S$614 per night
includes taxes & fees
Exceptional
(14 reviews)
Wicker Park: Cozy Fireplace, Grand Piano
Chicago
S$3,288
for 7 nights, 1 apartment
S$470 per night
includes taxes & fees
Exceptional
(9 reviews)
The Dakin Estate: 4BR Art Deco speakeasy duplex in Wrigleyville, 5 min from Wrigley Field. Designed for groups, it blends curated interiors, elevated finishes, and entertainment-focused spaces for Cubs games, concerts, and Chicago nightlife.
Chicago
S$6,287
for 7 nights, 1 apartment
S$898 per night
includes taxes & fees
Exceptional
(76 reviews)
Private Historic Coach House Wicker Park
Chicago
S$3,168
for 7 nights, 1 home
S$453 per night
includes taxes & fees
Exceptional
(10 reviews)
Elite 4BR Art Deco suite. Garage included.
Chicago
S$4,908
for 7 nights, 1 apartment
S$701 per night
includes taxes & fees
Exceptional
(38 reviews)
Lincoln Park Charm Near Everything + On site Parking Spot Included
Chicago
S$6,917
for 7 nights, 1 apartment
S$988 per night
includes taxes & fees
Exceptional
(193 reviews)
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Chicago
S$4,668
for 7 nights, 1 home
S$667 per night
includes taxes & fees
Exceptional
(113 reviews)
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Chicago
S$2,116
for 7 nights, 1 apartment
S$302 per night
includes taxes & fees
Exceptional
(101 reviews)
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Chicago
S$7,560
for 7 nights, 1 home
S$1,080 per night
includes taxes & fees
Exceptional
(114 reviews)
Wrigley Field/Lakeview -Entire Home- Large Groups!
Chicago
S$7,199
for 7 nights, 1 home
S$1,028 per night
includes taxes & fees
Exceptional
(32 reviews)
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Chicago
S$2,090
for 7 nights, 1 apartment
S$299 per night
includes taxes & fees
Exceptional
(63 reviews)
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
Chicago
S$4,124
for 7 nights, 1 apartment
S$589 per night
includes taxes & fees
Exceptional
(375 reviews)
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Chicago
S$1,874
for 7 nights, 1 apartment
S$268 per night
includes taxes & fees
Exceptional
(204 reviews)
1F Chicago's Little italy Graystone nearDowntown
Chicago
S$2,106
for 7 nights, 1 apartment
S$301 per night
includes taxes & fees
Exceptional
(22 reviews)
Chicago Bear Den
Chicago
S$2,096
for 7 nights, 1 apartment
S$299 per night
includes taxes & fees
Exceptional
(12 reviews)
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Chicago
S$2,669
for 7 nights, 1 apartment
S$381 per night
includes taxes & fees
Exceptional
(60 reviews)
Cozy two bedroom close to Wrigley Field
Chicago
S$3,331
for 7 nights, 1 apartment
S$476 per night
includes taxes & fees
Exceptional
(41 reviews)
Stylish Two Bedroom - A block from Wrigley Field
Chicago
S$2,793
for 7 nights, 1 apartment
S$399 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
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Sleeps 4 · 2 bedrooms · 1 bathroom
Relaxing Chicago Studio
Sleeps 4 · 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
Spacious 4-bedroom apartment with WiFi, AC in brilliant Chicago
Sleeps 9 · 4 bedrooms · 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
What is the most popular type of holiday rental accommodation in Uptown?
Apartments are the most popular style of holiday rental in Uptown, according to our data. Even if you've got something a little different in mind, Vrbo has holiday homes in all sizes and shapes. Browse our options to find your perfect pad.
How much does it cost to rent a holiday rental in Uptown?
Length of stay, property type and season are among the factors that can determine the price of a holiday home. Simply add your dates of travel to find your perfect match. From comfy cabins to expansive luxury villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Uptown?
Prices for beach houses in Uptown will vary depending on the size and style of the property and when you're travelling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your rental options and prices. From there you can use our filters to refine your search by ratings, nearby activities and more.
Are there pet-friendly holiday rentals in Uptown?
With 26 properties that welcome pets, your furry little friend can join in the fun on your Uptown getaway. Use our filter tool to search our pet-friendly holiday rentals and find the pawfect pad on Vrbo.
Can I rent a house with a pool in Uptown?
Tick the "pool" box in our filter tool and take your pick of two houses with private pools in Uptown on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your holiday property comes with its own pool.
What are popular rental amenities in Uptown?
A garden, a nearby waterfront and a lake view top the list of most popular rental amenities in Uptown. Whether you plan to travel solo, with your significant other or a group of family members, Vrbo will help you find a holiday rental that suits your tastes with all the features you're looking for.
Are there large group holiday rentals in Uptown?
With three properties that can sleep 10 or more people in Uptown, there's no need to cross anyone off the invite list. From family holidays to special events like weddings and birthday parties, Vrbo can help you find a large group rental that fits the occasion.
Are there holiday rentals in Uptown that welcome kids?
Bring the entire family together for an adventure in Uptown at one of our 26 family-friendly holiday properties. Lots of these stays provide amenities that are perfect for getaways with youngsters, like kitchens, extra bedrooms and outdoor spaces. Simply click on the "Properties good for families" filter and pick out your favourite.
What are the top attractions for families in Uptown?
There are lots of exciting things to see and do with the family in Uptown, such as:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there one-bedroom holiday rentals in Uptown?
Uptown has nine one-bedroom rentals on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom holiday rental is ideal if you're travelling with a friend or your partner. And with home comforts like air conditioning and more privacy than a standard hotel, you'll be able to relax while enjoying this amazing destination.
Can I find two-bedroom holiday rentals in Uptown?
Pick from five two-bedroom holiday homes in Uptown. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's space for whoever's fortunate enough to be joining in on the fun.
Are there holiday rentals with WiFi in Uptown?
You'll have a choice of 10 holiday rentals with WiFi in Uptown. If you want to disconnect from daily life during your trip, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Uptown?
Pick your travel dates and then make use of the filters to find holiday rentals with air conditioning in Uptown on Vrbo. With 26 air-conditioned properties on offer here, you can enjoy a comfortable and cool stay.
How old do you have to be to rent a holiday rental in Uptown?
The minimum required age is usually 16, 18 or 21. It can change across properties on Vrbo, so look at the rules of your chosen Uptown stay before making a booking.
How long can I rent a holiday rental in Uptown for?
The amount of time you can rent an Uptown holiday home for depends on the property. Just put in your preferred travel dates to view available options that offer long-term stays. They come with all the things you need to make your extended trip more convenient and enjoyable, such as kitchens and yards. Some properties might also offer discounted weekly or monthly prices, so you can stay longer for less money.
More holiday ideas
- Near North Side Holiday Rentals
- Hermosa Holiday Rentals
- Magnolia Glen Holiday Rentals
- Sauganash Holiday Rentals
- Ravenswood Holiday Rentals
- Arcadia Terrace Holiday Rentals
- Athenaeum Theatre Holiday Rentals
- Anshe Emet Synagogue Holiday Rentals
- Leather Archives & Museum Holiday Rentals
- Irving Park Holiday Rentals
- Humboldt Park Beach Holiday Rentals
- Advocate Illinois Masonic Medical Center Holiday Rentals
- St. Basil Greek Orthodox Church Holiday Rentals
- Broadway Playhouse Holiday Rentals
- Dave & Buster's Holiday Rentals
- Grace Abbott Homes Holiday Rentals
- Armour Square Holiday Rentals
- Millennium Park Holiday Rentals
- Fulton Market Holiday Rentals
- Park View Apartments Holiday Rentals
- Hamlin Park Holiday Rentals
- Streeterville Holiday Rentals
- North Side Holiday Rentals
- Apollo Theater Chicago Holiday Rentals
- Logan Square Holiday Rentals
- St. John Cantius Church Holiday Rentals
- Irving Park East Holiday Rentals
- Avondale Holiday Rentals
- Louis A. Weiss Memorial Hospital Holiday Rentals
- Thorek Memorial Hospital Holiday Rentals
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