Uptown (Chicago) Vacation Rentals - Uptown (Chicago), Illinois Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

-Lovely 5 BedRoom Unit in Uptown

-Lovely 5 BedRoom Unit in Uptown

5
3.0
12

Chicago Illinois Apartment From $500 per night (USD)

$Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground$

Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground

1
1.0
2

Chicago Illinois Apartment From $156 per night (USD)

$Barsala l Spacious, bright 1BD w\/ Fitness Center$

Barsala l Spacious, bright 1BD w\/ Fitness Center

1
1.0
2

Chicago Chicago Private vacation home Click For Pricing

$Dreamy Uptown 1BR w\/ Gym, Rooftop Pool, 2 blocks to L, by Blueground$

Dreamy Uptown 1BR w\/ Gym, Rooftop Pool, 2 blocks to L, by Blueground

1
1.0
2

Chicago Illinois Apartment From $111 per night (USD)

❤️ Spacious and Airy Apartment With Parking On Site!

❤️ Spacious and Airy Apartment With Parking On Site!

3
2.0
4

Chicago Illinois Apartment From $336 per night (USD)

The Bright Retreat in Andersonville

The Bright Retreat in Andersonville

1
1.0
4

Chicago Illinois Condo From $222 per night (USD)

Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!

Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!

3
2.0
6

chicago Illinois Condo From $200 per night (USD)

$3 Bedroom\/ 2 Bathroom Luxury Condo Andersonville$

3 Bedroom\/ 2 Bathroom Luxury Condo Andersonville

3
2.0
6

Chicago Illinois Apart-hotel From $537 per night (USD)

Great Location-Beautiful Friendly Andersonville Neighborhood

Great Location-Beautiful Friendly Andersonville Neighborhood

3
1.0
4

Chicago Illinois Apartment From $167 per night (USD)

$2BD\/2BA Near Wrigley, Lincoln Square. Family Friendly Boutique Hotel$

2BD\/2BA Near Wrigley, Lincoln Square. Family Friendly Boutique Hotel

2
2.0
4

Chicago Illinois Condo From $479 per night (USD)

Inviting Stylish Home with Covered Patio

Inviting Stylish Home with Covered Patio

1
1.0
4

Chicago Illinois Private vacation home From $291 per night (USD)

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

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

1
1.0
3

Chicago Illinois Apartment From $319 per night (USD)

2BR in Andersonville-Walk to train, beach, shops and restaurants!

2BR in Andersonville-Walk to train, beach, shops and restaurants!

2
1.0
4

Chicago Illinois Apartment From $148 per night (USD)

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

Beautiful 6BR mansion, 4 parking spots, sleeps 21! Walk to Wrigley & the lake!

6
4.0
21

Chicago Illinois Private vacation home From $1150 per night (USD)

$Amazing Uptown 1BR w\/ Roof & W\/D, 1 block to Red Line, by Blueground$

Amazing Uptown 1BR w\/ Roof & W\/D, 1 block to Red Line, by Blueground

1
1.0
2

Chicago Illinois Apartment From $140 per night (USD)

$Bright Uptown 1BR w\/ W\/D & Roof, near Aragon Ballroom, by Blueground$

Bright Uptown 1BR w\/ W\/D & Roof, near Aragon Ballroom, by Blueground

1
1.0
2

Chicago Illinois Apartment Click For Pricing

❤️ Lowest Rates! Spacious Duplex with Free Parking!

❤️ Lowest Rates! Spacious Duplex with Free Parking!

4
3.0
9

Chicago Illinois Apartment From $436 per night (USD)

$Airy Uptown 1BR w\/ Fire Pits & Indoor Pool, nr Beach, by Blueground$

Airy Uptown 1BR w\/ Fire Pits & Indoor Pool, nr Beach, by Blueground

1
1.0
2

Chicago Illinois Apartment From $118 per night (USD)

$Hip Uptown 1BR w\/ Rooftop & Grills, nr Hospital & Beach, by Blueground$

Hip Uptown 1BR w\/ Rooftop & Grills, nr Hospital & Beach, by Blueground

1
1.0
2

Chicago Illinois Apartment From $94 per night (USD)

$Charming Uptown 1BR w\/ Indoor Pool, nr Lakefront Trail, by Blueground$

Charming Uptown 1BR w\/ Indoor Pool, nr Lakefront Trail, by Blueground

1
1.0
2

Chicago Illinois Apartment From $144 per night (USD)

$Bright Uptown 1BR w\/ Gym w\/ Boxing Ring, nr Red Line, by Blueground$

Bright Uptown 1BR w\/ Gym w\/ Boxing Ring, nr Red Line, by Blueground

1
1.0
2

Chicago Illinois Apartment From $139 per night (USD)

$Amazing Uptown 1BR w\/ Gym & Indoor Pool, nr L Red Line, by Blueground$

Amazing Uptown 1BR w\/ Gym & Indoor Pool, nr L Red Line, by Blueground

1
1.0
2

Chicago Illinois Apartment From $80 per night (USD)

Free Parking Luxury Loft Getaway Uptown Montrose Beach WFH Gym Pet Friendly

Free Parking Luxury Loft Getaway Uptown Montrose Beach WFH Gym Pet Friendly

1
1.0
2

Chicago Illinois Apartment From $147 per night (USD)

Majestic Modern Style Loft Montrose Beach WFH Gym RARE. Pet Friendly

Majestic Modern Style Loft Montrose Beach WFH Gym RARE. Pet Friendly

1
1.0
2

Chicago Illinois Apartment From $155 per night (USD)

Barsala l Modern studio, fitness center & kitchen

Barsala l Modern studio, fitness center & kitchen

1.0
2

Chicago Chicago Private vacation home Click For Pricing

Full of Charm Studio Apartment Nearby Shops

Full of Charm Studio Apartment Nearby Shops

1.0
2

Chicago Illinois Apartment From $192 per night (USD)

$Luxe 2BR Apartment w\/ In-Unit Laundry$

Luxe 2BR Apartment w\/ In-Unit Laundry

2
2.0
4

Chicago Illinois Apartment From $256 per night (USD)

PRIVATE Boho vintage condo with sunrooms and plants in Historic Andersonville

PRIVATE Boho vintage condo with sunrooms and plants in Historic Andersonville

3
1.0
6

Chicago Illinois Condo Click For Pricing

Pet Friendly! Can You Smell the Popcorn and Peanuts? One Mile from Wrigley Field and Room for All the Super Fans! by RedAwning

Pet Friendly! Can You Smell the Popcorn and Peanuts? One Mile from Wrigley Field and Room for All the Super Fans! by RedAwning

6
4.0
12

Chicago Illinois Private vacation home From $860 per night (USD)

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by RedAwning

Sheridan Park Stunner! No Matter if You Are in Town for Business or Fun This Property Has You Covered by RedAwning

3
2.0
6

Chicago Illinois Apartment From $469 per night (USD)

$Beautiful Uptown 1BR w\/ Gym, Rooftop Pool, 2 blocks to L, by Blueground$

Beautiful Uptown 1BR w\/ Gym, Rooftop Pool, 2 blocks to L, by Blueground

1
1.0
2

Chicago Illinois Apartment From $118 per night (USD)

$Dreamy Uptown Studio w\/ Roof & W\/D, near Aragon Ballroom, by Blueground$

Dreamy Uptown Studio w\/ Roof & W\/D, near Aragon Ballroom, by Blueground

1.0
2

Chicago Illinois Apartment Click For Pricing

1BR Delightful Apt in Ravenswood | Shops & Dining

1BR Delightful Apt in Ravenswood | Shops & Dining

1
1.0
2

Chicago Illinois Apartment From $187 per night (USD)

Elite Studio Apartment in Uptown near Shops

Elite Studio Apartment in Uptown near Shops

1.0
2

Chicago Illinois Apartment From $179 per night (USD)

Elegant Hideaway in the Heart of Andersonville

Elegant Hideaway in the Heart of Andersonville

2
1.0
4

Chicago Illinois Condo From $324 per night (USD)

Cozy Uptown Studio with In-unit laundry & Wi-Fi!

Cozy Uptown Studio with In-unit laundry & Wi-Fi!

1.0
2

Chicago Illinois Apartment From $168 per night (USD)

$Studio Apartment w\/ In-Unit Laundry, Near Shops!$

Studio Apartment w\/ In-Unit Laundry, Near Shops!

1.0
2

Chicago Illinois Apartment From $178 per night (USD)

$Hidden Andersonville \/ Wrigleyville Gem!!!$

Hidden Andersonville \/ Wrigleyville Gem!!!

1
1.0
3

Chicago Illinois Private vacation home From $123 per night (USD)

Cozy Studio in Bustling Ravenswood Neighborhood

Cozy Studio in Bustling Ravenswood Neighborhood

1
1.0
2

Chicago Illinois Apartment Click For Pricing

Large 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen

Large 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen

2
2.0
6

Chicago Illinois Condo Click For Pricing

$Eclectic Home w\/ Hot Tub < 2 Mi to Wrigley Field$

Eclectic Home w\/ Hot Tub < 2 Mi to Wrigley Field

4
3.0
8

Chicago Illinois Private vacation home From $450 per night (USD)

$Artistic Stylish Modern Loft Uptown Getaway RARE\n\n$

Artistic Stylish Modern Loft Uptown Getaway RARE\n\n

1
1.0
2

Chicago Illinois Apartment From $138 per night (USD)

$Maisons de Promettre\nModern Elegance Suite in the Heart of Uptown Chicago$

Maisons de Promettre\nModern Elegance Suite in the Heart of Uptown Chicago

1
1.0
2

Chicago Illinois Apartment From $148 per night (USD)

$Regal Stylish Loft Uptown Montrose Beach - Serene Getaway WFH Gym Pets Allowed\n\n$

Regal Stylish Loft Uptown Montrose Beach - Serene Getaway WFH Gym Pets Allowed\n\n

1
1.0
2

Chicago Illinois Apartment From $146 per night (USD)

$Luxury Modern Uptown Studio Loft Serene Montrose Beach WFH Gym Pet Friendly\n\n$

Luxury Modern Uptown Studio Loft Serene Montrose Beach WFH Gym Pet Friendly\n\n

1
1.0
2

Chicago Illinois Apartment From $147 per night (USD)

$Elegant Modern Stylish Loft Mountain Vibe Montrose Beach WFH Gym Pet Friendly\n\n$

Elegant Modern Stylish Loft Mountain Vibe Montrose Beach WFH Gym Pet Friendly\n\n

1
1.0
2

Chicago Illinois Apartment From $157 per night (USD)

$Deluxe Uptown 1BR w\/ Gym, Pool & Rooftop, nr Red Line, by Blueground$

Deluxe Uptown 1BR w\/ Gym, Pool & Rooftop, nr Red Line, by Blueground

1
1.0
2

Chicago Illinois Apartment From $107 per night (USD)

$Chic Uptown 1BR w\/ Rooftop & Gym, nr Hospital & Beach, by Blueground$

Chic Uptown 1BR w\/ Rooftop & Gym, nr Hospital & Beach, by Blueground

1
1.0
2

Chicago Illinois Apartment From $117 per night (USD)

$Delightful Uptown 1BR w\/ Indoor Pool, 2 Blocks to Beach, by Blueground$

Delightful Uptown 1BR w\/ Indoor Pool, 2 Blocks to Beach, by Blueground

1
1.0
2

Chicago Illinois Apartment From $160 per night (USD)

$Classic Uptown 1BR w\/ Fire Pits & Rooftop, nr L Red Line, by Blueground$

Classic Uptown 1BR w\/ Fire Pits & Rooftop, nr L Red Line, by Blueground

1
1.0
2

Chicago Illinois Apartment From $120 per night (USD)

Barsala l Bright Studio with full kitchen

Barsala l Bright Studio with full kitchen

1.0
2

Chicago Chicago Private vacation home From $202 per night (USD)

PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by RedAwning

PET FRIENDLY! Desirable Sheridan Park is a Safe, Vibrant, and Welcoming Area you are Sure to Love by RedAwning

3
2.0
6

Chicago Illinois Apartment From $563 per night (USD)

Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway by RedAwning

Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway by RedAwning

1
1.0
4

Chicago Illinois Condo From $310 per night (USD)

Uptown studio apartment with breathing views

Uptown studio apartment with breathing views

1
1.0
4

Chicago Illinois Apartment From $150 per night (USD)

Nice & Comfy Uptown Studio Apt near Shops & Dining

Nice & Comfy Uptown Studio Apt near Shops & Dining

1.0
2

Chicago Illinois Apartment From $165 per night (USD)

Convenient studio located in Buena Park (pet- friendly)

Convenient studio located in Buena Park (pet- friendly)

1
1.0
2

Chicago Illinois Apartment From $122 per night (USD)

Homey|Vintage|2BR Uptown

Homey|Vintage|2BR Uptown

2
1.0
4

Chicago Illinois Apartment From $210 per night (USD)

Elegant modern apartment

Elegant modern apartment

2
2.0
4

Chicago Illinois Apartment From $431 per night (USD)

Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!

Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!

4
2.0
9

Chicago Illinois Condo From $879 per night (USD)

Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9

Gorgeous 4 Bedroom with Pool Table steps from Wrigley Field Sleeps 9

4
2.0
9

Chicago Illinois Condo From $1019 per night (USD)

Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building

Featured on the Travel Channel, 4 Bedroom 2 Bath in Wrigley Rooftop Building

4
2.0
9

CHICAGO Illinois Condo From $954 per night (USD)

Contemporary 2BR Flat Right Next to Wrigley Field & Transit ❤️ Cubs!

Contemporary 2BR Flat Right Next to Wrigley Field & Transit ❤️ Cubs!

2
1.0
5

Chicago Illinois Apartment From $306 per night (USD)

Cozy Lakeview apartment near Train Station

Cozy Lakeview apartment near Train Station

1
1.0
2

Chicago Illinois Apartment From $153 per night (USD)

Lakeview Lux - Apt #2

Lakeview Lux - Apt #2

3
1.0
9

Chicago Illinois Apartment Click For Pricing

Lakeview Lux - Apt #1

Lakeview Lux - Apt #1

3
1.0
8

Chicago Illinois Apartment Click For Pricing

Large Apt with 2 Car Garage and EV Charger! Walk to Wrigley Field & Brown Line!

Large Apt with 2 Car Garage and EV Charger! Walk to Wrigley Field & Brown Line!

4
3.0
6

Chicago Illinois Apartment From $839 per night (USD)

Spacious, Clean and Steps from Wrigley Field!

Spacious, Clean and Steps from Wrigley Field!

2
2.0
5

Chicago Illinois Condo From $269 per night (USD)

$Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground$

Sunny Lakeview 1BR w\/ Rooftop & Gym, nr Lincoln Park, by Blueground

1
1.0
2

Chicago Illinois Apartment From $116 per night (USD)

$Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground$

Open Lakeview 2BR w\/ Gym & Grills, nr Lakefront Trail, by Blueground

2
2.0
4

Chicago Illinois Apartment From $267 per night (USD)

$Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$

Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground

1
1.0
2

Chicago Illinois Apartment From $119 per night (USD)

Cozy Garden Unit Located in North Center

Cozy Garden Unit Located in North Center

1
1.0
2

Chicago Illinois Apartment From $273 per night (USD)

Custom 5 Bedrooms, Family Friendly, Centrally Located, WITH YARD and Parking!

Custom 5 Bedrooms, Family Friendly, Centrally Located, WITH YARD and Parking!

5
4.0
8

Chicago Illinois Private vacation home From $299 per night (USD)

Beautiful town house

Beautiful town house

3
2.0
5

Chicago Illinois Private vacation home From $150 per night (USD)

Fremont St. Guesthouse - Unit 1

Fremont St. Guesthouse - Unit 1

3
2.0
6

Chicago Illinois Condo From $339 per night (USD)

Quiet Spacious 2BR Apt walk to Train, near Shops

Quiet Spacious 2BR Apt walk to Train, near Shops

2
1.0
4

Chicago Illinois Apartment From $185 per night (USD)

$Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$

Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground

1
1.0
2

Chicago Illinois Apartment From $86 per night (USD)

$Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground$

Sleek Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground

1
1.0
2

Chicago Illinois Apartment From $122 per night (USD)

$Classic Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground$

Classic Lakeview 2BR w\/ Deck, Pool & Gym, nr Lincoln Park, by Blueground

2
2.0
4

Chicago Illinois Apartment Click For Pricing

Sophisticated 2BR Apt 5 mins Walk to Wrigley

Sophisticated 2BR Apt 5 mins Walk to Wrigley

2
1.0
6

Chicago Illinois Apartment From $242 per night (USD)

Modern 1BR Oasis in the Heart of the City

Modern 1BR Oasis in the Heart of the City

1
1.0
2

Chicago Illinois Apartment From $192 per night (USD)

2-Bedroom Indulging Condo Apt in Festive Boystown

2-Bedroom Indulging Condo Apt in Festive Boystown

2
1.0
4

Chicago Illinois Apartment From $329 per night (USD)

Charming 1BR Apt in North Center Near Shops

Charming 1BR Apt in North Center Near Shops

1
1.0
2

Chicago Illinois Apartment From $218 per night (USD)

Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.

Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.

1
1.0
3

Chicago Illinois Apartment From $135 per night (USD)

$Amazing Lakeview 1BR w\/ Rooftop Pool, near Wrigley Field, by Blueground$

Amazing Lakeview 1BR w\/ Rooftop Pool, near Wrigley Field, by Blueground

1
1.0
2

Chicago Illinois Apartment From $97 per night (USD)

$Stunning Lakeview 1BR w\/ Rooftop Pool, near Wrigley Field, by Blueground$

Stunning Lakeview 1BR w\/ Rooftop Pool, near Wrigley Field, by Blueground

1
1.0
2

Chicago Illinois Apartment From $131 per night (USD)

$Wrigleyville Condo, 1\/2 block from Wrigley Field. Sleeps 10$

Wrigleyville Condo, 1\/2 block from Wrigley Field. Sleeps 10

3
3.0
6

Chicago Illinois Condo From $359 per night (USD)

Spacious & Modern Family Friendly North Center Apt - Solar-Powered

Spacious & Modern Family Friendly North Center Apt - Solar-Powered

2
1.0
6

Chicago Illinois Apartment From $153 per night (USD)

5 Bedroom Wrigleyville experience right by stadium

5 Bedroom Wrigleyville experience right by stadium

5
2.0
11

Chicago Illinois Apartment From $575 per night (USD)

Real Comfort in a 2BR APT close to Wrigley Field

Real Comfort in a 2BR APT close to Wrigley Field

2
1.0
4

Chicago Illinois Apartment From $239 per night (USD)

Your 1BR Homey Haven in Vibrant Chicago

Your 1BR Homey Haven in Vibrant Chicago

1
1.0
2

Chicago Illinois Apartment From $239 per night (USD)

❤️ Modern 2BR Apt Right next to Wrigley Field & Transit

❤️ Modern 2BR Apt Right next to Wrigley Field & Transit

2
1.0
5

Chicago Illinois Apartment From $341 per night (USD)

$Vintage Wrigley 1Br\/1Ba with parking$

Vintage Wrigley 1Br\/1Ba with parking

1
1.0
4

Chicago Illinois Apartment From $333 per night (USD)

$Roomy Lakeview 1BR w\/ W\/D, Gym, near Lakefront Trail, by Blueground$

Roomy Lakeview 1BR w\/ W\/D, Gym, near Lakefront Trail, by Blueground

1
1.0
2

Chicago Illinois Apartment From $174 per night (USD)

Best Lincoln Square Location - Spacious 2 bedroom

Best Lincoln Square Location - Spacious 2 bedroom

2
1.0
4

Chicago Illinois Condo From $189 per night (USD)

Wrigleyville Inn, Beautiful Modern 1 Bedroom, Steps from Wrigley Field

Wrigleyville Inn, Beautiful Modern 1 Bedroom, Steps from Wrigley Field

1
1.0
4

Chicago Illinois Condo From $379 per night (USD)

$Wrigleyville\/Boystown Basement Gem$

Wrigleyville\/Boystown Basement Gem

3
1.0
5

Chicago Illinois Apartment From $595 per night (USD)

Penthouse Level, Stunning Wrigley Stay

Penthouse Level, Stunning Wrigley Stay

2
1.0
6

Chicago Illinois Condo From $900 per night (USD)

Lakeview Greystone One Block From Wrigleyfield

Lakeview Greystone One Block From Wrigleyfield

3
1.0
6

Chicago Illinois Apartment Click For Pricing

Retro Apartment in Andersonville

Retro Apartment in Andersonville

2
1.0
4

Chicago Illinois Apartment From $168 per night (USD)

Modern Wrigley Oasis with Parking!

Modern Wrigley Oasis with Parking!

2
2.0
6

Chicago Illinois Condo From $266 per night (USD)

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