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 $1187 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 $1187 per night (USD)
VRBO
From $173 per night (USD)
Expedia
Amazing Edgewater 2BR, nr Lake Michigan, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Edgewater Beach furnished two bedroom ...
From $173 per night (USD)
Expedia
From $1297 per night (USD)
VRBO
Eddy House, Roscoe Village Haven
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Steps away from Roscoe Village dining & shopping and a short train to the Mag Mile. Enjoy the best Chicago has to offer ...
From $1297 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This newly updated 2 bedroom, 1 bath condo has everything you need to make your Chicago stay perfect! The home was thou ...
From $378 per night (USD)
Expedia
From $811 per night (USD)
VRBO
Wrigley 2 bedroom 2 bath with free parking & yard!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: My home is a very large 2 bedroom 2 bath condo 3 blocks (6 minute stroll) from Wrigley Field. It's 20 minutes ...
From $811 per night (USD)
VRBO
$Classic Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$
From $88 per night (USD)
Expedia
Classic Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Edgewater Beach furnished one bedroom ...
From $88 per night (USD)
Expedia
From $485 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 $485 per night (USD)
VRBO
From $1307 per night (USD)
Expedia
Luxurious, custom built single family home near Wrigley
Bedrooms:
6
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 $1307 per night (USD)
Expedia
$Premium Lakeview 2BR w\/ W\/D, nr Wrigley Field & Lake, by Blueground$
From $142 per night (USD)
VRBO
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 $142 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy Studio in Bustling Ravenswood Neighborhood
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This small but cozy apartment is located in the heart of Ravenswood near amazing restaurants and bars, close to Wrigley ...
Click For Pricing
Expedia
$Wrigleyville Jungle House w\/ game room basement party room for large groups!$
From $1407 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 $1407 per night (USD)
VRBO
From $903 per night (USD)
Expedia
Spacious Wrigley Duplex | Large Entertainment Room
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to our spacious and stylish apartment, located just steps away from the iconic Wrigley Field in Chicago! This is ...
From $903 per night (USD)
Expedia
From $582 per night (USD)
VRBO
Fremont St. Guesthouse - Unit 1
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Classic Chicago Brownstone, updated 3 bedroom and 2 bathroom high end, 1st floor condo. Located on beautiful Fremont Str ...
From $582 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $421 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 $421 per night (USD)
VRBO
Click For Pricing
Expedia
Centrally Located Chicago Loft 2 blocks from the Lakeshore!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautifully updated 1 Bedroom, 1 Bathroom loft in Lakeview has all you'll need during your stay in Chicago! Conveni ...
Click For Pricing
Expedia
From $388 per night (USD)
VRBO
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 $388 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Cozy 2 bedroom apartment in Wrigleyville
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the heart of Wrigleyville, this 2 bedroom, 1.5 bathrooms in situated right on Clark St. This property comes w ...
From $481 per night (USD)
Expedia
$Luxe Lakeview 1BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground$
From $207 per night (USD)
VRBO
Luxe Lakeview 1BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Lake View East. . It’ll be easy to simply show up and s ...
From $207 per night (USD)
VRBO
$Modern Lakeview 2BR w\/ Roftop & Gym, nr Trail & Park, by Blueground$
From $257 per night (USD)
Expedia
Modern Lakeview 2BR w\/ Roftop & Gym, nr Trail & 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 s ...
From $257 per night (USD)
Expedia
$Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground$
Click For Pricing
VRBO
Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
Click For Pricing
VRBO
$Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground$
From $216 per night (USD)
Expedia
Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Discover the best of Chicago, with this two bedroom apartment in Lake View East. with balcony views over the city. It’ll ...
From $216 per night (USD)
Expedia
$The Irving Park Hideaway – Prime Location w\/ Patio & Parking!$
From $406 per night (USD)
VRBO
The Irving Park Hideaway – Prime Location w\/ Patio & Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
-1 Garage Spot INCLUDED!!!! - Fully furnished unit with everything you'll need for your stay. - Third-floor rear apar ...
From $406 per night (USD)
VRBO
$Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$
From $157 per night (USD)
Expedia
Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $157 per night (USD)
Expedia
From $416 per night (USD)
VRBO
Spacious, Clean and Steps from Wrigley Field!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Enjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking distance fr ...
From $416 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Lakeview Lux - Apt #2
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $140 per night (USD)
Expedia
From $154 per night (USD)
VRBO
Lakeview Lux - Apt #1
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $154 per night (USD)
VRBO
From $782 per night (USD)
Expedia
St.Bens, Jacuzzi, EV Parking! 4 beds, Walk to Wrigley Field & Brown Line!
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Looking for a spacious, stylish, and fully-equipped home in the heart of Chicago? Book your stay now and make this beau ...
From $782 per night (USD)
Expedia
$Chicago Home w\/ Hot Tub < 2 Mi to Wrigley Field$
Click For Pricing
VRBO
Chicago Home w\/ Hot Tub < 2 Mi to Wrigley Field
Bedrooms:
3
Bathrooms:
6
Sleeps:
8
- R23000095595 - 3,000 Sq Ft - Projector - Spacious Backyard - 8 Mi to Downtown Chicago Explore the vibrant city of Chi ...
Click For Pricing
VRBO
$-Lovely 5BD\/3BR\/3Parking on premises\/Sleeps 14 guests\/Andersonville$
From $1109 per night (USD)
Expedia
-Lovely 5BD\/3BR\/3Parking on premises\/Sleeps 14 guests\/Andersonville
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $1109 per night (USD)
Expedia
From $160 per night (USD)
VRBO
MODERN COMPLETELY REMODELED Bright, Spacious Flat STEPS from Wrigley Field &Bars
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LOCATION! LOCATION! LOCATION!!! You will absolutely love this NEWLY REMODELED 1100 sq ft apartment in the HEART OF WRIG ...
From $160 per night (USD)
VRBO
From $153 per night (USD)
Expedia
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 $153 per night (USD)
Expedia
From $462 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 $462 per night (USD)
VRBO
$Stylish Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$
From $135 per night (USD)
Expedia
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 eas ...
From $135 per night (USD)
Expedia
$The Chicago Hotel Collection - Wrigleyville\n$
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $977 per night (USD)
Expedia
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 $977 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
$Lakeview\/Wrigley Townhouse$
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
$Stylish 3BD 2BA Apt Near Wrigley w\/ Parking x3$
From $707 per night (USD)
Expedia
Stylish 3BD 2BA Apt Near Wrigley w\/ 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 $707 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Artistic Loft Rooftop Uptown Montrose Beach GymWFH
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $408 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Regal Stylish Loft Rooftop Beachfront WFH Gym RARE
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $372 per night (USD)
Expedia
From $196 per night (USD)
VRBO
Elegant Style Loft Montrose Beach Rooftop WFH Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $196 per night (USD)
VRBO
From $969 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 $969 per night (USD)
Expedia
$Wrigley Penthouse w\/Private Roof Deck and Parking$
From $584 per night (USD)
VRBO
Wrigley Penthouse w\/Private Roof Deck and Parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Stunning 3BR, 2.5BA penthouse with chef's kitchen, Viking appliances, private rooftop deck, Weber grill, smoker, master ...
From $584 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Spacious Lakeview Hideway with Parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Fall in love with the Cubs fervor, Boystown, iconic eats, and local spots of Chicago from this 4-bedroom, 2-bath vacatio ...
From $442 per night (USD)
Expedia
From $518 per night (USD)
VRBO
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 $518 per night (USD)
VRBO
$3Bed\/2Bath Penthouse Steps from the Brown Line$
From $180 per night (USD)
Expedia
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)
Expedia
From $481 per night (USD)
VRBO
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 $481 per night (USD)
VRBO
$Wrigley\/Lakeview Gem- Walk to Wrigley Field\/ Parking available!$
From $279 per night (USD)
Expedia
Wrigley\/Lakeview Gem- Walk to Wrigley Field\/ Parking available!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
GO CUBS GO!! Just renovated and less than a block from iconic Wrigley Field is a cozy 1 BR garden unit. Home to the Cubs ...
From $279 per night (USD)
Expedia
From $681 per night (USD)
VRBO
SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Our home is located in the quiet, but centrally located Buena Park neighborhood in an updated antique building. The loca ...
From $681 per night (USD)
VRBO
From $163 per night (USD)
Expedia
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 $163 per night (USD)
Expedia
From $401 per night (USD)
VRBO
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 $401 per night (USD)
VRBO
$Chic Urban Retreat Near Wrigley Field w\/Parking$
From $447 per night (USD)
Expedia
Chic Urban Retreat Near Wrigley Field w\/Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to our stylish 2-bedroom, 2-bathroom condo nestled in the Lakeview/Southport neighborhood, the vibrant heart of ...
From $447 per night (USD)
Expedia
$Peaceful Cozy Loft Beach\/City Views Rooftop GymWFH$
From $340 per night (USD)
VRBO
Peaceful Cozy Loft Beach\/City Views Rooftop GymWFH
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $340 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Elegant Duplex with Chef's Kitchen Near Wrigley Field by AllSet Turnover
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**HOSTING 32+ NIGHTS** Make yourself at home in this elegant Wrigleyville duplex down, just steps from Chicago's ...
From $249 per night (USD)
Expedia
From $407 per night (USD)
VRBO
Beautiful and Relaxing Wrigleyville Apartment
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Located across the street from Wrigley Field, this recently remodeled and thoughtfully decorated apartment provides a pe ...
From $407 per night (USD)
VRBO
From $420 per night (USD)
VRBO
Wrigleyville Condo 2 Blks from Lake & Train
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red lin ...
From $420 per night (USD)
VRBO
From $287 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 $287 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Majestic Modern Style Beach Views Rooftop WFH Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $391 per night (USD)
Expedia
From $230 per night (USD)
VRBO
Bright Modern 4Bd 2Ba in the Heart of Wrigleyville by AllSet Turnover
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
**Hosting Long-Term Stays of 32+ Nights** Immerse yourself in the heartbeat of Wrigleyville for your next Chicago ex ...
From $230 per night (USD)
VRBO
From $388 per night (USD)
Expedia
The Lincoln Square Hideaway
Bedrooms:
1
Bathrooms:
4
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 $388 per night (USD)
Expedia
$New home w\/view & party deck - 2nd Floor$
From $1231 per night (USD)
VRBO
New home w\/view & party deck - 2nd Floor
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...
From $1231 per night (USD)
VRBO
$3Bed\/2Bath Wrigley home w\/view & party deck 443 ft from Wrigley Field - 3rd Fl$
From $1238 per night (USD)
Expedia
3Bed\/2Bath Wrigley home w\/view & party deck 443 ft from Wrigley Field - 3rd Fl
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...
From $1238 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
$Sunny Apartment Just 2 Blocks from Wrigley and Boystown\n\n$
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
$Wonderful Edgewater 1BR w\/ Patio Deck & Gym, near lake, by Blueground$
From $135 per night (USD)
VRBO
Wonderful Edgewater 1BR w\/ Patio Deck & Gym, near lake, by Blueground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the best of Chicago, with this one bedroom apartment in Edgewater Beach. . It’ll be easy to simply show up and ...
From $135 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Designer Apartment 10 Min Walk to Wrigley!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Stunning 2 bedroom apartment with 1 King bed and 1 Queen bed. You are a 5 min walk to Wrigley Field, Home of t ...
From $367 per night (USD)
Expedia
From $245 per night (USD)
VRBO
2-bedroom apartment just 2 minutes drive to Wrigley Field
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape to the heart of Chicago's vibrant North Center neighborhood in this charming 2-bedroom apartment. Situated just a ...
From $245 per night (USD)
VRBO
From $599 per night (USD)
Expedia
Wrigleyville Suites Room 2
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $599 per night (USD)
Expedia
$Hip Edgewater 2BR w\/ Patio Deck, near Beach & Red Line, by Blueground$
From $154 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 ...
From $154 per night (USD)
VRBO
From $1210 per night (USD)
Expedia
2-Story 4-Bedroom Condo: 3-minute walk to Wrigley Field. King Bed
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Just one block from Wrigley Field! Includes air hockey, ping-pong, foosball, and oversized Connect 4 in the basement ga ...
From $1210 per night (USD)
Expedia
From $518 per night (USD)
VRBO
Duplex 3 Bed 2 Bath Apt Steps from Lincoln Square
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Summary: Welcome to your perfect Chicago getaway! This spacious 3-bedroom, 2-bathroom multi-level apartment offers every ...
From $518 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Updated 3 Bedroom Chicago Historic Andersonville
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $386 per night (USD)
Expedia
From $332 per night (USD)
VRBO
2BR Apartment in Andersonville Neighborhood.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 bedroom apartment in a prime location, 2 minutes from the center of Andersonville shopping and dining. Easy access to ...
From $332 per night (USD)
VRBO
Click For Pricing
Expedia
The Lytle House Loft
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Lytle House Loft is a one of a kind residence located in the heart of the Edgewater neighborhood in Chicago, just bl ...
Click For Pricing
Expedia
From $854 per night (USD)
VRBO
The Broasis at Wrigley
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
I took a perfectly nice flat on a beautiful street and filled it with great things...I want my guests to feel less like ...
From $854 per night (USD)
VRBO
From $3246 per night (USD)
Expedia
Six-Bedrooms in Wrigleyville
Bedrooms:
2
Bathrooms:
6
Sleeps:
16
Enjoy the combination of your own 2 apartments in Wrigleyville - the city's center of nightlife, restaurants, and baseba ...
From $3246 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Wrigleyville Suites Room 3
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $249 per night (USD)
VRBO
From $1591 per night (USD)
Expedia
Wrigleyville 3BD Condo
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1591 per night (USD)
Expedia
$Wrigleyville Garden 3BR\/9beds Pod$
From $1499 per night (USD)
VRBO
Wrigleyville Garden 3BR\/9beds Pod
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $1499 per night (USD)
VRBO
From $775 per night (USD)
VRBO
Wrigleyville Garden 1BR
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
We just finished renovating this history solid brick building to create a magical home for your getaway in Chicago. Ste ...
From $775 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Chicago Bear Den
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
New renovation, 2.5 blocks from iconic Wrigley field, quiet safe street, and a comfortable spacious layout. Steps from ...
From $234 per night (USD)
VRBO
From $599 per night (USD)
Expedia
Wrigleyville Suites Room 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $599 per night (USD)
Expedia
From $417 per night (USD)
VRBO
The Burrow at Wrigley
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Expect to find a relatively dark and moody interior filled with interesting things. The location is exceptional, with th ...
From $417 per night (USD)
VRBO
From $1579 per night (USD)
Expedia
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!
Bedrooms:
5
Bathrooms:
10
Sleeps:
26
Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more ...
From $1579 per night (USD)
Expedia
From $76 per night (USD)
VRBO
Wrigleyville- Corporate, Business, Travel Nurse
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Stay comfortably in Chicago at this 1-bedroom condo. The bedroom features a nice queen bed, and the 1 and half bathrooms ...
From $76 per night (USD)
VRBO
Click For Pricing
Expedia
Relaxing City Haven
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Your cozy getaway awaits in Chicago at this fabulous house. With 3 bedrooms including 2 queen beds and 1 sofa bed, this ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Luxurious Andersonville Oasis
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to our stunning retreat, perfect for families or friends seeking a stylish getaway. This beautifully designed un ...
Click For Pricing
VRBO
From $2491 per night (USD)
Expedia
Wrigley 4BR Home, Sleeps 10, Firepit
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Experience Wrigley Ville in this spacious 4-bedroom, 2-bath home, perfect for groups. The house combines two units, offe ...
From $2491 per night (USD)
Expedia
$Wrigleyville 2BR w\/Parking, Firepit & Workspace for Remote Work$
From $758 per night (USD)
VRBO
Wrigleyville 2BR w\/Parking, Firepit & Workspace for Remote Work
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Discover the charm of Chicago’s North Side in this cozy 2-bedroom, 1-bathroom apartment, just steps from iconic Wrigley ...
From $758 per night (USD)
VRBO
$Terrific Edgewater 1BR w\/ Fitness Center, Lounge & W\/D, by Bluedground$
From $124 per night (USD)
Expedia
Terrific Edgewater 1BR w\/ Fitness Center, Lounge & W\/D, by Bluedground
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Edgewater Beach furnished one bedro ...
From $124 per night (USD)
Expedia
$The Grand Vic: Large 5BD\/3BA Home +Garage\n$
From $1063 per night (USD)
VRBO
The Grand Vic: Large 5BD\/3BA Home +Garage\n
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to the Grand Vic, an extraordinary home nestled in the heart of the city’s historic North Center neighborhood. T ...
From $1063 per night (USD)
VRBO
$Bright 2BR Apt w\/ Private Entrance & Laundry$
From $326 per night (USD)
Expedia
Bright 2BR Apt w\/ Private Entrance & Laundry
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This central location can't be beat! Situated near Wrigley Field, you'll be on the border of Lakeview and Wrigleyville, ...
From $326 per night (USD)
Expedia
From $2393 per night (USD)
VRBO
Vacation home just 2 minutes drive to Wrigley Field
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
This brand new Greystone is in the heart of North Center Lakeview, Chicago. Walking distance to Wrigley, Andersonville, ...
From $2393 per night (USD)
VRBO
From $815 per night (USD)
Expedia
NEW! Charming 3bd Bungalow in Vibrant Andersonville ~ RA498886
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our vintage Andersonville bungalow! Built in the 1920s, our home exudes character with original floors, wind ...
From $815 per night (USD)
Expedia
From $804 per night (USD)
VRBO
Spacious 4-bedroom condo in wonderful Chicago with WiFi, AC
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Chicago is waiting for you at this 4-bedroom condo. Step into this enchanting space with 3 queen beds and 1 king bed, pe ...
From $804 per night (USD)
VRBO
From $693 per night (USD)
Expedia
2BR Wrigleyville Apt Free Parking, Office, Fire Pit & Outdoor Space
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to your perfect Chicago retreat! This cozy 2-bedroom, 1-bathroom apartment in vibrant Wrigleyville offers everyt ...
From $693 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Entire Apt in Heart of Chicago
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This Chicago apartment boasts 2 inviting bedrooms with 2 queen beds. The cozy living room features a sofa bed for extra ...
From $225 per night (USD)
VRBO
$Walk to Bars\/Restaurants\/Cubs Games! Sleeps 16 in a HUGE house!$
From $1703 per night (USD)
Expedia
Walk to Bars\/Restaurants\/Cubs Games! Sleeps 16 in a HUGE house!
Bedrooms:
2
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 $1703 per night (USD)
Expedia

Search Your Destination Now!

Uptown (Chicago) Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 236 Rentals