Uptown vacation rentals
We found 2,216 vacation rentals — enter your dates for availability
Discover a selection of 6 homes and other vacation rentals in Uptown that are perfect for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll have the amenities you expect and more, which might include parking and a hot tub. You'll be able to choose a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Uptown
Showing deals for:Nov 7 - Nov 14
Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
8.08.0 out of 10 rating
Very good
(14 reviews)
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
Chicago, IL
15% off
Price is CA $424
CA $424
CA $4,546 total
CA $4,546 total
includes taxes & fees
Image gallery for Luxury Downtown Penthouse with Private Rooftop!
9.09.0 out of 10 rating
Wonderful
(19 reviews)
Luxury Downtown Penthouse with Private Rooftop!
Chicago, IL
5% off
Price is CA $530
CA $530
CA $5,369 total
CA $5,369 total
includes taxes & fees
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
10% off
Price is CA $450
CA $450
CA $4,503 total
CA $4,503 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(15 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, Illinois
10% off
Price is CA $871
CA $871
CA $8,441 total
CA $8,441 total
includes taxes & fees
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(22 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
10% off
Price is CA $3,719
CA $3,719
CA $34,638 total
CA $34,638 total
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, Illinois
10% off
Price is CA $515
CA $515
CA $5,059 total
CA $5,059 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.89.8 out of 10 rating
Exceptional
(11 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
10% off
Price is CA $571
CA $571
CA $5,787 total
CA $5,787 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $530
CA $530
CA $5,341 total
CA $5,341 total
includes taxes & fees
Image gallery for #1801 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(41 reviews)
#1801 - Kasa Magnificent Mile Chicago
Chicago, Illinois
10% off
Price is CA $441
CA $441
CA $4,156 total
CA $4,156 total
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, Illinois
10% off
Price is CA $590
CA $590
CA $5,959 total
CA $5,959 total
includes taxes & fees
Image gallery for Breathtaking Downtown Penthouse B - Sleeps 11
9.09.0 out of 10 rating
Wonderful
(23 reviews)
Breathtaking Downtown Penthouse B - Sleeps 11
Chicago, IL
5% off
Price is CA $606
CA $606
CA $6,169 total
CA $6,169 total
includes taxes & fees
Image gallery for Modern 3BR Penthouse in the Loop | Roof Deck
9.49.4 out of 10 rating
Exceptional
(40 reviews)
Modern 3BR Penthouse in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $729
CA $729
CA $7,208 total
CA $7,208 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(56 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, Illinois
10% off
Price is CA $572
CA $572
CA $5,651 total
CA $5,651 total
includes taxes & fees
Image gallery for 2nd Floor Flat in River North - 2S
9.89.8 out of 10 rating
Exceptional
(21 reviews)
2nd Floor Flat in River North - 2S
Chicago, Illinois
5% off
Price is CA $530
CA $530
CA $5,369 total
CA $5,369 total
includes taxes & fees
Image gallery for Luxury Designer Penthouse North - Pool - Gold Coast
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Luxury Designer Penthouse North - Pool - Gold Coast
Chicago, Illinois
10% off
Price is CA $713
CA $713
CA $6,957 total
CA $6,957 total
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(15 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
10% off
Price is CA $941
CA $941
CA $9,261 total
CA $9,261 total
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
10% off
Price is CA $352
CA $352
CA $3,503 total
CA $3,503 total
includes taxes & fees
Image gallery for Corner 3BR in Streeterville | Views | Roof Deck
9.69.6 out of 10 rating
Exceptional
(32 reviews)
Corner 3BR in Streeterville | Views | Roof Deck
Chicago, Illinois
10% off
Price is CA $538
CA $538
CA $5,420 total
CA $5,420 total
includes taxes & fees
Image gallery for Luxury Loft Collection 01 - Terrace - River North
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Luxury Loft Collection 01 - Terrace - River North
Chicago, IL
10% off
Price is CA $962
CA $962
CA $9,255 total
CA $9,255 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(19 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $821
CA $821
CA $8,323 total
CA $8,323 total
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
10% off
Price is CA $231
CA $231
CA $2,683 total
CA $2,683 total
includes taxes & fees
Image gallery for Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
1010 out of 10 rating
Exceptional
(42 reviews)
Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square
Chicago, IL
19% off
Price is CA $301
CA $301
CA $3,069 total
CA $3,069 total
includes taxes & fees
Image gallery for 2-bedroom apartment just 2 minutes drive to Wrigley Field
9.49.4 out of 10 rating
Exceptional
(32 reviews)
2-bedroom apartment just 2 minutes drive to Wrigley Field
Chicago, IL
10% off
Price is CA $279
CA $279
CA $2,820 total
CA $2,820 total
includes taxes & fees
Image gallery for #1901 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(59 reviews)
#1901 - Kasa Magnificent Mile Chicago
Chicago, Illinois
10% off
Price is CA $441
CA $441
CA $4,156 total
CA $4,156 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Uptown
Map Attractions
4
Hutchinson Street Historic District
Find the best place to stay - Uptown
Stunning, Spacious, & Sun-soaked 2BR Uptown Condo by AllSet Turnover
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Serene 3-bedroom apartment in Chicago
Sleeps 7 · 3 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Luxurious 3 Bedroom Apartment in Chicago
Sleeps 5 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
16 reviews(16 reviews)
Relaxing Chicago Studio
Sleeps 4 · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Uptown Studio Gem Sum
Sleeps 2 · 1 bathroom
8.08.0 out of 10
Very goodvery good
1 review(1 review)
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Sleeps 2 · 1 bedroom · 1 bathroom
8.68.6 out of 10
Excellentexcellent
15 reviews(15 reviews)
Top rated rentals - Uptown
Chicago vacation
1010 out of 10
Exceptionalexceptional
188 reviews(188 reviews)
Paul's place was perfect for the four of us and came as advertised!! Close to all forms of public transit so it was easy to get to downtown, or just about anywhere else. If you don't want to go far, Andersonville has many dining options a close walk away.
Stephen Y.
Stayed Aug 2024
Attractive place
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Roomy and light. We really liked the extra touches, such as the bookshelves of Chicago and urban-themed books. Quite well equipped and comfortable, with thoughtful extras such as a bag of good coffee.
A step stool in the kitchen would help, since some of the shelves are out of reach for those of us on the short side. And the the pullout bed was a bit awkward to manage.
Also note that you need to climb three flights of stairs to get there.
Margaret W.
Stayed Oct 2023
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
It was a great place to stay!!
Gordon S.
Stayed Mar 2020
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, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental accommodation in Uptown?
Apartments are the most popular style of vacation rental in Uptown, according to our data. Even if you've got something a little different in mind, Vrbo has vacation homes in all sizes and shapes. Browse our options to find your perfect pad.
How much does it cost to rent a vacation rental in Uptown?
Length of stay, property type and season are among the factors that can determine the price of a vacation home. Simply add your dates of travel to find your perfect match. From comfy cabins to expansive luxury villas, all Vrbo vacation 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 traveling. 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 vacation 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 vacation 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 vacation 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 vacation rental that suits your tastes with all the features you're looking for.
Are there large group vacation 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 vacations to special events like weddings and birthday parties, Vrbo can help you find a large group rental that fits the occasion.
Are there vacation rentals in Uptown that welcome kids?
Bring the entire family together for an adventure in Uptown at one of our 26 family-friendly vacation 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 favorite.
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 vacation rentals in Uptown?
Uptown has nine one-bedroom rentals on offer. Usually situated in desirable areas thanks to their smaller size, a one-bedroom vacation rental is ideal if you're traveling 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 vacation rentals in Uptown?
Pick from five two-bedroom vacation 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 vacation rentals with WiFi in Uptown?
You'll have a choice of 10 vacation 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 vacation rentals with air conditioning in Uptown?
Pick your travel dates and then make use of the filters to find vacation 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 vacation 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 vacation rental in Uptown for?
The amount of time you can rent an Uptown vacation 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.