Uptown (Chicago), Illinois Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Uptown (Chicago), Illinois on RentalSaver.com!

Uptown (Chicago) Rentals

From $135 per night (USD)
VRBO
Airy Lakeview Studio, w/ W/D, Gym, near Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this studio apartment in Lake View East with high floor views over the city. It’ll be ...
From $135 per night (USD)
VRBO
From $956 per night (USD)
Expedia
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
3 Bedroom, 2 Full Bathrooms Sleeps 7 people. Located in Garden Unit in a Wrigley Rooftop Building. Located directly ac ...
From $956 per night (USD)
Expedia
From $1361 per night (USD)
VRBO
Luxurious, custom built single family home near Wrigley
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to one of the best home rentals in Chicago! Built in 2015, this 5 bedroom, 6 bathroom also boasts has an office, ...
From $1361 per night (USD)
VRBO
From $111 per night (USD)
Expedia
Premium Lakeview 2BR w/ W/D, nr Wrigley Field & Lake, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Lake View East with views over the city. It’ll be easy ...
From $111 per night (USD)
Expedia
From $1153 per night (USD)
VRBO
Wrigleyville Jungle House w/ game room basement party room for large groups!
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Welcome to this jungle-themed home in Wrigleyville! With room for 15 guests, 6 bedrooms and a huge basement, this place ...
From $1153 per night (USD)
VRBO
From $631 per night (USD)
VRBO
Spacious Wrigley Duplex | Large Entertainment Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our spacious and stylish apartment, located just steps away from the iconic Wrigley Field in Chicago! This is ...
From $631 per night (USD)
VRBO
From $946 per night (USD)
VRBO
Lakeview Lux - 20min to Wrigley - Free Parking - Sleeps 17+
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $946 per night (USD)
VRBO
From $387 per night (USD)
Expedia
Spacious 3BR in Lakeview - Walk to Wrigley - Family Friendly, Newly Renovated!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to Chicago and Lakeview! From this apartment, you’re a 10-15 minute walk from Wrigley field, 15-20 minutes from ...
From $387 per night (USD)
Expedia
From $180 per night (USD)
VRBO
3Bed/2Bath Penthouse Steps from the Brown Line
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
This condo is a gorgeous, spacious and bright 3Bed/2Bath Penthouse in the heart of North Center. It includes a home offi ...
From $180 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Spacious 3BR in Andersonville - Just off Clark St
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy local living on the 1st floor of our classic Chicago 2-flat with modern touches and free street parking. Our locat ...
From $396 per night (USD)
Expedia
From $80 per night (USD)
VRBO
Stylish Edgewater 1BR w/ Gym, Deck & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach with views over the city. It’ll be easy ...
From $80 per night (USD)
VRBO
$The Chicago Hotel Collection - Wrigleyville\n$
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Expedia
The Chicago Hotel Collection - Wrigleyville\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Chicago Hotel Collection - Wrigleyville is located in Wrigleyville, a neighborhood in Chicago, and is in the enterta ...
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Expedia
From $957 per night (USD)
VRBO
LARGE LUX 6BD, 4BA HOME +garage & patio
Bedrooms:
4
Bathrooms:
6
Sleeps:
13
Escape into this Chicago Masterpiece! Guests love this home because: - Surrounded by top-notch restaurants/retail on ...
From $957 per night (USD)
VRBO
From $232 per night (USD)
VRBO
Modern Apartment on Quiet Street in Andersonville
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Remodeled, spacious private apartment in Andersonville, the coolest neighborhood in the US, according to TimeOut magazin ...
From $232 per night (USD)
VRBO
From $217 per night (USD)
VRBO
Charming Wrigleyville Home Close to the Cubs!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy Chicago while staying in our private guest suite in a fantastic Wrigleyville location! We are the main residents o ...
From $217 per night (USD)
VRBO
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Expedia
Lakeview/Wrigley Townhouse
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
About this space Make yourself at home in this cozy Wrigleyville townhouse that is a fun short walk to Chicago's legenda ...
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Expedia
From $430 per night (USD)
VRBO
Cozy Train Vibes + Rare Parking x3
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy a neighborhood feel in a big city. Welcome to our North Center 3 bedroom, 2 bathroom apartment on a quiet tree lin ...
From $430 per night (USD)
VRBO
From $210 per night (USD)
Expedia
MODERN COMPLETELY REMODELED Bright, Spacious Flat STEPS from Wrigley Field &Bars
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
LOCATION! LOCATION! LOCATION!!! You will absolutely love this NEWLY REMODELED 1100 sq ft apartment in the HEART OF WRIG ...
From $210 per night (USD)
Expedia
From $193 per night (USD)
VRBO
A laid-back studio few minutes from Wrigley Field
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your stay in Chicago, Lakeview in this cozy, newly remodeled studio! This studio is located in a walking distance ...
From $193 per night (USD)
VRBO
From $564 per night (USD)
Expedia
Wrigley Field Views & Cubs Vibes – Stay Across the Street!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay Steps from Wrigley Field – Book Your Dream Chicago Getaway Fast!Now Accepting 2025 Cubs Season Bookings! -1 parkin ...
From $564 per night (USD)
Expedia
From $169 per night (USD)
VRBO
Root! Root! Root! For the Home Team in this Modern Studio
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Cozy and quiet studio apartment just 2 blocks from Wrigley Field and less than a 5-minute walk to the center of Wrigleyv ...
From $169 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Charming 2-bedroom 1 block to Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The whole group will enjoy easy access to everything from this centrally located place, less than a 5-minute walk to the ...
From $377 per night (USD)
Expedia
From $204 per night (USD)
VRBO
Elegant Duplex with Chef's Kitchen Near Wrigley Field by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You won't want to leave this stunning Wrigleyville duplex, located just steps from Chicago's legendary Wrigley Field! T ...
From $204 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Private Gem, quiet street in Andersonville -1 bedroom + sofa bed + easy parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This newly renovated, private 1-bedroom garden apartment is located on a quiet residential block in Andersonville's Lake ...
From $333 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Hip Edgewater 2BR w/ Patio Deck, near Beach & Red Line, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Edgewater Beach. It’ll be easy to simply show up and st ...
From $312 per night (USD)
VRBO
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Expedia
Private Coach house near Lincoln Square!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville ...
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Expedia
$Sunny Apartment Just 2 Blocks from Wrigley and Boystown\n\n$
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VRBO
Sunny Apartment Just 2 Blocks from Wrigley and Boystown\n\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Located on a quiet, tree-lined street, the apartment sits on the second storey of a classic Chicago house in Lakeview—a ...
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VRBO
From $276 per night (USD)
Expedia
The Lincoln Square Hideaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
As you walk into your private 1st floor apartment from Western Ave, you’ll be greeted by a stunning wide-open great room ...
From $276 per night (USD)
Expedia
From $1109 per night (USD)
VRBO
Walk to Bars/Restaurants/Cubs Games! Sleeps 16 in a HUGE house!
Bedrooms:
3
Bathrooms:
6
Sleeps:
16
Welcome to the ultimate Disco Cowboy getaway! This huge house is perfect for bach parties and friends/family trips! Loc ...
From $1109 per night (USD)
VRBO
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Expedia
Beautiful corporate housing 4 bed; full utilities; charming&quaint!
Bedrooms:
2
Bathrooms:
4
Sleeps:
4
Beautifully furnished and equipped for easy living. Weekly or bi-weekly house cleaning can be arranged for a fee. It w ...
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Expedia
From $991 per night (USD)
VRBO
wriglelyville 4BR Retreat New Build + Parking + 1min walk cta
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This brand-new 4-bedroom 3-bath luxury home is located in the heart of Wrigleyville just 1 minute from the Red Line Addi ...
From $991 per night (USD)
VRBO
From $455 per night (USD)
VRBO
Wrigleyville Private Guesthouse
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
New Guesthouse ideal for 6+guests 1 block from Southport brown line station, 1/2 mile from Wrigley Field & red line stat ...
From $455 per night (USD)
VRBO
From $750 per night (USD)
VRBO
The Wrigleyville Penthouse with Private Rooftop!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Steps from Wrigley Field, my 2 bed/2 bath + Den penthouse with a private rooftop is the perfect “home base” for your gro ...
From $750 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Relaxing in Ravenswood - This Neighborhood is Great for Any Group and Close to Everything! by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Our 2 bed garden apartment in Ravenswood will be the ideal home base for your stay! Located in one of Chicago's vibrant ...
From $248 per night (USD)
Expedia
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VRBO
Charming House in Lakeview - 1895. Walk to Wrigley
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
About this space Great city living in this bright, comfy, farmhouse style home. Perfect for entertaining with the whole ...
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VRBO
From $185 per night (USD)
VRBO
Fully restored 1900's 2-Flat on Chicago’s family friendly quiet North Side.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
When I renovated this building my dream was to maintain the look and feel of a 1911 city farmhouse building's charm but ...
From $185 per night (USD)
VRBO
From $510 per night (USD)
VRBO
Lovely 3 Bedroom condo near Wrigley!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
My charming 3-bedroom apartment has everything you need for your Chicago trip. The unit comes with washer/dryer in build ...
From $510 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover Chicago's charm in this newly designed 2-bedroom condo! Located a few blocks away from the heart of Lincoln Sq ...
From $233 per night (USD)
Expedia
From $333 per night (USD)
VRBO
The Irving Park Hideaway – Prime Location w/ Patio & Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
-Third floor rear apartment with outdoor patio and one garage spot. -1 Garage Spot INCLUDED!!!! - Fully furnished unit ...
From $333 per night (USD)
VRBO
From $78 per night (USD)
Expedia
Luxe Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach with views over the city. It’ll be easy ...
From $78 per night (USD)
Expedia
From $77 per night (USD)
VRBO
Ideal Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Edgewater Beach furnished one b ...
From $77 per night (USD)
VRBO
From $1651 per night (USD)
VRBO
Luxury Wrigleyville condo steps from Wrigley
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
New construction property that has 4 bedrooms, one with king, two with queen beds, and one with a queen bed and bunk bed ...
From $1651 per night (USD)
VRBO
From $162 per night (USD)
VRBO
Cute and Cozy 2 Bedroom
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Enjoy Classic decor in a spacious two bedroom one bathroom. Large eat-in kitchen and laundry in the basement! Tony's gro ...
From $162 per night (USD)
VRBO
From $98 per night (USD)
Expedia
Modern Edgewater 1BR w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach with views over the city. It’ll be easy ...
From $98 per night (USD)
Expedia
From $113 per night (USD)
VRBO
Hip Edgewater Studio w/ Gym, Deck & Lounge, 5 blocks to L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach with views over the city. It’ll be easy ...
From $113 per night (USD)
VRBO
From $177 per night (USD)
Expedia
Trendy Lakeview 1BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Lake View East with views over the city. It’ll be easy ...
From $177 per night (USD)
Expedia
From $397 per night (USD)
VRBO
Stylish Two Bedroom - A block from Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Come stay at this gorgeous, clean, renovated apartment in beautiful Lakeview/Wrigleyville. The unit is located on a beau ...
From $397 per night (USD)
VRBO
From $323 per night (USD)
Expedia
Light Filled with Tasteful Pops of Color - You Will Love This Mid-Century Modern Gem by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
If you love Mid-Century Modern decor you will love this apartment. The light- filled main family room and sun porch is ...
From $323 per night (USD)
Expedia
From $384 per night (USD)
VRBO
Perfect for Groups! Steps to the Beach and Room for All! Enjoy All Andersonville Has to Offer! by AllSet Turnover
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our charming three-bedroom duplex in trendy Andersonville is steps to Foster beach, antique shopping and so many food o ...
From $384 per night (USD)
VRBO
From $1228 per night (USD)
Expedia
The Wrigleyville Deluxe -Steps from Wrigley Sleeps 10
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Welcome to The Wrigleyville Deluxe. Perfect for large groups. 2 full Kitchens. 3 full baths. Sleeps 10. 1 King bed. 4 ...
From $1228 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Upscale Lakeview 2BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $207 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Modern Lakeview 2BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Lake View East. It’ll be easy to simply show up and sta ...
From $221 per night (USD)
Expedia
From $116 per night (USD)
VRBO
Ideal Lakeview 1BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
From $116 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Warm|Cozy|Lovely|1BR|Lincoln Sq.|
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $350 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Comfy Lincoln Square guest apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit, recently remodeled, is in the basement of our 127 year old Victorian home. It has its own separate entry thr ...
From $241 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Large and quiet 1 bedroom 1 bathroom Garden unit located in a typical Chicago 2 flat building type. We are exactly betw ...
From $252 per night (USD)
VRBO
From $197 per night (USD)
VRBO
Comfy Garden Suite in Andersonville
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A comfortable garden unit in a well cared for 3-flat, in a wonderful and safe neighborhood. Easy access to the lake fro ...
From $197 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Cute, Cozy, Elegant Budlong Woods
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Book with us and enjoy classic charm and elegant décor located in the Budlong woods neighborhood. Experience a great nig ...
From $132 per night (USD)
Expedia

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Uptown (Chicago) Rentals

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Results: 258 Rentals