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Home in Chicago, Illinois

Chicago Sky

5 bedrooms

7 beds

4 bathrooms

16 guests

4500 sq. ft.

About the property

Wander Chicago Sky is an opulent urban escape offering unparalleled luxury and recreation. This exquisite residence features a lively game room perfect for entertainment, a rejuvenating hot tub for ultimate relaxation, and a serene sauna to melt away the day's stresses. Experience sophisticated comfort and indulgence in a prime Chicago setting, promising an unforgettable retreat.
Property License: R25000126997

Where you’ll sleep

Bedroom 1

1 king bed

Bedroom 2

1 king bed

Bedroom 3

1 king bed

Bedroom 4

2 full bunk beds

Bedroom 5

2 full bunk beds

Bedroom 1

1 king bed

Bedroom 2

1 king bed

Bedroom 3

1 king bed

Bedroom 4

2 full bunk beds

Bedroom 5

2 full bunk beds

Amenities

Common Amenities

  • Game Room
  • Ping pong table
  • City view
  • Wifi
  • Free parking
  • Hot water
  • Carbon monoxide detector
  • Air conditioning
  • Patio
  • Smoke detector
  • First aid kit
  • Fire extinguisher
  • Balcony

Rooftop

  • BBQ Area
  • BBQ Utensils
  • Outdoor seating
  • Sauna
  • Hot tub
  • Outdoor dining area

Common Area

  • TV
  • Desk

Living Room

  • TV

Dining Room

  • Dining table

Kitchen

  • Oven
  • Cooking basics
  • Stove
  • Microwave
  • Freezer
  • Fridge
  • Dishwasher
  • Dishes
  • Coffee maker
  • Coffee
  • Kettle
  • Tea
  • Spices
  • Silverware
  • Cleaning supplies
  • Wine glasses

Bedroom 1

  • TV
  • Closet
  • Hangers
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 1

  • Ensuite bathroom
  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap
  • Bathtub

Bedroom 2

  • TV
  • Closet
  • Hangers
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 2

  • Ensuite bathroom
  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap
  • Bathtub

Bedroom 3

  • TV
  • Closet
  • Hangers
  • Ceiling fan
  • Bed linens

Ensuite Bathroom 3

  • Ensuite bathroom
  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap

Bedroom 4

  • Hammock
  • Bed linens

Bedroom 5

  • Desk
  • Bed linens

Bathroom 1

  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Shampoo
  • Conditioner
  • Body soap

Laundry Room

  • Washer
  • Dryer
  • Cleaning supplies

Gym

  • Mini golf
  • Gym
  • Exercise equipment

Theater

  • Movie Theater
  • TV

Game Room

  • Pool table
  • Poker Table
  • Arcade machine
  • Air hockey
  • Shuffleboard

4.8 · 80 reviews

Where you’ll be

Chicago, Illinois 60647, United States

Chicago, Illinois, United States
41.91555779999999-87.69618249999999
Timezone: America/Chicago

Restaurants

Eataly

Eataly is a vibrant Italian food hall where you can enjoy authentic regional dishes, shop for high-quality Italian ingredients, and learn cooking techniques in an energetic, market-style setting. Its open kitchens and diverse eateries create a lively, immersive Italian culinary experience.

Giordano's

Giordano’s is a Chicago institution famous for its legendary deep-dish, double-crust stuffed pizza, crafted with fresh ingredients and served in a lively, family-friendly atmosphere—perfect for sharing hearty Italian classics with friends or savoring a slice of authentic Windy City tradition.

Kasama

Kasama is Chicago’s first Michelin-starred Filipino restaurant, offering a warm, inviting atmosphere where traditional flavors meet modern fine dining through a creative tasting menu and casual daytime bakery fare. It’s a celebration of Filipino culture and cuisine in a cozy, café-style setting.

Wildberry Pancakes & Cafe

Wildberry Pancakes & Cafe offers a warm, welcoming atmosphere where you can enjoy perfectly fluffy pancakes, flavorful omelets, and classic breakfast favorites made with fresh, seasonal ingredients. It's a beloved spot for a memorable breakfast or brunch in Chicago.

Cindy's Rooftop

Cindy's Rooftop offers stunning views of Millennium Park and Lake Michigan, serving seasonal comfort food and inventive cocktails in a vibrant, stylish setting. Its open-air terrace and glass atrium create a memorable dining experience.

Pequod's Pizza

Pequod's Pizza offers a unique Chicago pan-style deep-dish experience with its signature caramelized crust, rich cheese pull, and flavorful tomato sauce, all served in a cozy, lively atmosphere perfect for savoring hearty, award-winning pies.

Lou Malnati's Pizzeria

Lou Malnati's Pizzeria serves authentic Chicago-style deep dish pizza with a flaky, buttery crust, fresh Wisconsin mozzarella, and a signature sausage blend, all crafted from a family recipe dating back to 1943. Its warm, family-friendly atmosphere celebrates Chicago’s pizza heritage.

Swissotel Chicago

The Palm at Swissotel Chicago offers a vibrant blend of prime aged steaks, fresh seafood, and Italian classics in an elegant setting with stunning views of the Chicago River and city skyline. Guests enjoy a refined yet inviting atmosphere perfect for any occasion.

Au Cheval

Au Cheval in Chicago’s Fulton Market is renowned for its legendary double cheeseburger topped with thick-cut bacon and a fried egg, served in a lively, bustling diner setting that offers a true comfort food experience. Its vibrant atmosphere and open kitchen make every visit memorable.

The Dearborn

The Dearborn is a vibrant urban American tavern in the heart of Chicago’s Loop, where classic comfort food meets creative twists and a welcoming, lively atmosphere—think tufted leather booths, vintage-inspired decor, and heartfelt service rooted in decades of Irish hospitality.

Attractions

Millennium Park

Millennium Park offers a unique blend of art, architecture, and entertainment, featuring iconic landmarks like "The Bean" and the Jay Pritzker Pavilion. It's perfect for anyone interested in culture, photography, and scenic city views.

Wrigley Field

Wrigley Field offers an unforgettable baseball experience with its historic charm, iconic ivy-covered outfield walls, and lively Wrigleyville atmosphere, perfect for sports fans and anyone who loves classic American culture and vibrant game-day traditions.

Field Museum

Explore the Field Museum, home to over 30 million artifacts, including Sue the T. Rex, and discover a world of natural history and culture. This iconic museum is perfect for families and anyone curious about the wonders of the past.

Lincoln Park Zoo

Discover the wonders of wildlife right in the heart of Chicago at Lincoln Park Zoo, where you can meet nearly 200 species, explore lush gardens, and enjoy free daily animal encounters—perfect for families, animal lovers, and anyone seeking a fun, accessible escape into nature.

Starbucks Reserve Roastery

Step inside the world’s largest Starbucks, where every floor brings a new coffee adventure—from rare brews and artisan Italian bites to rooftop city views. Coffee lovers and curious explorers alike will find something to savor in this immersive, multi-sensory destination on Chicago’s Magnificent Mile.

Navy Pier

Soaring above Lake Michigan on the Centennial Wheel, Navy Pier offers breathtaking skyline views, lively entertainment, and a vibrant mix of dining and shopping—perfect for families, thrill-seekers, and anyone looking to experience Chicago’s iconic waterfront charm.

Willis Tower

Experience breathtaking views from the Skydeck atop Willis Tower, the highest observation deck in the U.S., where thrill-seekers can step onto The Ledge—a glass balcony extending 4.3 feet over Chicago’s skyline. Perfect for anyone who loves spectacular cityscapes and unforgettable photo moments.

Shedd Aquarium

Discover a mesmerizing underwater world at Shedd Aquarium, where you can marvel at beluga whales, vibrant coral reefs, and Amazonian creatures—all under one roof. Perfect for families, animal lovers, and curious explorers of all ages who want to get up close with aquatic life in the heart of Chicago.

The Art Institute of Chicago

The Art Institute of Chicago offers an extraordinary journey through centuries of art, featuring iconic masterpieces like American Gothic and The Old Guitarist, perfect for art lovers and curious explorers alike seeking inspiration and cultural discovery.

Cloud Gate

Cloud Gate, or "The Bean," is a stunning, mirror-like sculpture in Chicago’s Millennium Park that reflects and distorts the city skyline, offering a unique interactive experience perfect for art lovers, photographers, and visitors seeking a memorable urban landmark.

Things to know

Cancellation policy

Cancel within 24 hours for a full refund.

Property rules

Pets not allowed

No smoking - fees will apply

Events require approval

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

16 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Apr 30, 2026$418Available
May 1, 2026$991Not Available
May 2, 2026$1001Not Available
May 3, 2026$340Not Available
May 4, 2026$316Not Available
May 5, 2026$323Not Available
May 6, 2026$504Not Available
May 7, 2026$450Available
May 8, 2026$796Not Available
May 9, 2026$749Not Available
May 10, 2026$295Not Available
May 11, 2026$272Not Available
May 12, 2026$235Available
May 13, 2026$275Available
May 14, 2026$464Available
May 15, 2026$1303Not Available
May 16, 2026$1327Not Available
May 17, 2026$641Available
May 18, 2026$592Available
May 19, 2026$582Available
May 20, 2026$397Available
May 21, 2026$605Available
May 22, 2026$1614Not Available
May 23, 2026$1612Not Available
May 24, 2026$884Available
May 25, 2026$435Available
May 26, 2026$380Available
May 27, 2026$472Available
May 28, 2026$1038Available
May 29, 2026$1667Available
May 30, 2026$1736Not Available
May 31, 2026$702Not Available
Jun 1, 2026$712Not Available
Jun 2, 2026$386Not Available
Jun 3, 2026$824Not Available
Jun 4, 2026$1067Not Available
Jun 5, 2026$1898Available
Jun 6, 2026$1921Not Available
Jun 7, 2026$627Not Available
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Jun 10, 2026$560Not Available
Jun 11, 2026$1063Not Available
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Jun 19, 2026$2424Available
Jun 20, 2026$2422Available
Jun 21, 2026$760Available
Jun 22, 2026$570Available
Jun 23, 2026$572Available
Jun 24, 2026$789Available
Jun 25, 2026$1168Available
Jun 26, 2026$2134Not Available
Jun 27, 2026$2064Not Available
Jun 28, 2026$690Not Available
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Jun 30, 2026$563Not Available
Jul 1, 2026$648Not Available
Jul 2, 2026$1046Available
Jul 3, 2026$1755Available
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Jul 5, 2026$585Available
Jul 6, 2026$532Available
Jul 7, 2026$523Available
Jul 8, 2026$1025Available
Jul 9, 2026$1092Available
Jul 10, 2026$2032Not Available
Jul 11, 2026$2050Not Available
Jul 12, 2026$511Available
Jul 13, 2026$495Available
Jul 14, 2026$598Available
Jul 15, 2026$664Available
Jul 16, 2026$1092Not Available
Jul 17, 2026$2276Not Available
Jul 18, 2026$2365Not Available
Jul 19, 2026$647Available
Jul 20, 2026$789Available
Jul 21, 2026$744Available
Jul 22, 2026$631Available
Jul 23, 2026$1134Not Available
Jul 24, 2026$2184Not Available
Jul 25, 2026$2179Available
Jul 26, 2026$646Not Available
Jul 27, 2026$593Not Available
Jul 28, 2026$1003Not Available
Jul 29, 2026$1151Available