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Chicago Sky
Chicago, Illinois

Wander Chicago Sky

Wander Chicago Sky

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16 guests
7 beds
4 bathrooms
1/79
PropertyFull kitchenLarge TV
16 guests
5 bedrooms
7 beds
4 bathrooms
4500 sq. ft.
Wander Chicago Sky is an opulent urban escape offering unparalleled luxury and recreation.
Flexible check-in & out
Check-in after 4:00pm • Check-out before 10:00amNo pets allowed
Easy cancellation
Cancel within 24 hours for a full refund.
Pristine homes, no to-do lists
Arrive to five star cleaning • No chores at checkout • Just lock up and go

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

Hotel-grade amenities

Wander is the best of both worlds. The quality of a luxury hotel with the comfort of a private vacation home just for you and your guests.

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

  • Ceiling fan
  • TV
  • Closet
  • Hangers
  • 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

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

Where you’ll be

Located in the vibrant Logan Square neighborhood, this property is nested in the heart of Chicago’s creative and cultural scene. Guests can pend the day exploring nearby boutique shops, art galleries, and street murals, or unwind at one of the area’s trendy cafés and breweries.
Chicago, Illinois, United States
41.91555779999999-87.69618249999999
Timezone: America/Chicago

Getting there

Clybourn

Clybourn Station is a key transportation hub in Chicago, serving Metra's Union Pacific North and Northwest Lines. It offers convenient access to nearby neighborhoods like Bucktown and DePaul.

Chicago O'Hare International Airport

Chicago O'Hare International Airport offers a comprehensive travel experience with unlimited Wi-Fi, spa services, and a yoga room, alongside accessible facilities for disabled passengers. It connects to over 228 destinations worldwide, making it a major global hub.

Healy

Healy serves as a key transportation point, notably connecting visitors to Denali National Park via the Parks Highway. It offers convenient access to surrounding communities and natural attractions.

Chicago Midway International Airport

Chicago Midway International Airport offers convenient access to downtown Chicago via the Orange Line, a single terminal with quick gate connections, free Wi-Fi, diverse dining and shopping, and comprehensive accessibility services, making travel smooth and comfortable for all passengers.

Irving Park

Irving Park is a well-connected Chicago transit hub offering easy transfers between the CTA Brown and Blue Lines, Metra commuter rail, and multiple bus routes, making it a convenient gateway to key city destinations.

Addison Blue Line Station

Addison Blue Line Station offers quick, convenient access to downtown Chicago and O'Hare Airport, with frequent trains running every few minutes and connections to local bus routes. Located in the Kennedy Expressway median, it serves the Avondale and Irving Park neighborhoods and nearby key destinations like the Villa District.

Gary/Chicago International Airport

Gary/Chicago International Airport offers convenient access near Chicago with full-service facilities including corporate hangars, US Customs, and efficient passenger and cargo services, all supported by a nearly 9,000-foot runway and modern amenities for a smooth travel experience.

Ohare Airport Taxi LLC

O'Hare Airport Taxi LLC offers reliable, 24/7 flat-rate transportation services with a focus on comfort and punctuality. Their fleet includes various vehicles, accommodating groups of all sizes with options like car seats for families.

A2 Global Shipping

A2 Global Shipping offers reliable air, ocean, and trucking freight services worldwide, specializing in commercial cargo, personal effects, and international relocations with expert handling of hazardous and high-value goods. Their extensive network ensures efficient, cost-effective shipping solutions across multiple continents.

RideCar Limousine

RideCar Limousine offers reliable, comfortable group transportation with a modern fleet—including limos, SUVs, and shuttles—for airport transfers, events, and corporate travel across Illinois and beyond. Enjoy seamless booking, professional drivers, and amenities designed to make every journey smooth and stress-free.

Kedzie

Kedzie serves as a vital transportation hub in Chicago, offering convenient connections to various parts of the city via the Blue Line and multiple bus routes. It provides easy access to key destinations across the urban landscape.

Grayland

Grayland’s transportation hub offers convenient connections through Grays Harbor Transit, linking local cities with key destinations like Olympia and Centralia, making regional travel easy and accessible. The nearby Westport-Grayland Park & Ride enhances commuter options for seamless transit.

A2 Global Shipping

A2 Global Shipping offers reliable air, ocean, and trucking freight services for commercial cargo and personal effects worldwide, with specialized handling for hazardous and high-value goods. They provide seamless international relocations and import/export solutions through a broad global network.

Western Avenue

Western Avenue is a convenient transit hub offering seamless connections between Metra trains and multiple bus routes, providing easy access to key destinations across Chicago and surrounding areas. Its accessible platforms and central location make commuting straightforward and efficient.

Addison Red Line Station

Addison Red Line Station offers direct, convenient access to Wrigley Field and connects riders to Chicago’s North and South Sides via 24-hour service on the Red Line, making it a key hub for sports fans and city commuters alike.

Irving Park Brown Line Station

Irving Park Brown Line Station offers convenient access to Chicago’s North Side with seamless connections to multiple bus routes and rapid transit, making it easy to reach downtown, local neighborhoods, and key destinations across the city. The station is fully accessible and supports efficient transfers for a smooth commute.

Black Kard Transportation

Black Kard Transportation offers reliable, 24/7 ground transportation with luxury SUVs, limos, and buses, serving local, regional, and international airports including Chicago’s O'Hare and Midway. Their professional chauffeurs provide meet-and-greet service, live flight tracking, and seamless airport transfers for business or leisure travelers.

Addison Brown Line Station

Addison Brown Line Station connects Chicago’s North Side with seamless access to the Loop, local bus routes, and vibrant neighborhoods—offering a convenient, elevated stop steps from shops, cafes, and easy transfers for commuters and explorers alike.

Restaurants

Walmart Supercenter

Walmart Supercenter offers a wide range of specialty items, including gourmet meats and seafood, unique deli options, and a variety of international flavors. It also features a convenient grab-and-go section for quick snacks and meals.

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.

Whole Foods Market

Whole Foods Market offers a curated selection of globally inspired snacks, unique fusion foods, and fresh, high-quality produce, making it a destination for adventurous eaters seeking innovative flavors and wholesome ingredients. Discover international dumplings, crunchy textures, and trend-forward treats all in one place.

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.

Jewel-Osco

Jewel-Osco offers a wide selection of fresh, quality foods including unique deli specialties like stuffed grape leaves, marinated mushrooms, and spicy honey, alongside options for specialty diets such as vegan, keto, and gluten-free. Their in-store bakery, deli, and local favorites make every meal feel special.

Trader Joe's

Trader Joe's is known for its unique seasonal snacks, specialty produce, and a wide range of artisanal cheeses and ready-made meals that make grocery shopping both fun and flavorful. Their exclusive items like pumpkin spice mini cheesecake and unexpected dips keep customers coming back year-round.

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.

Walmart Supercenter

Walmart Supercenter offers a wide variety of affordable groceries, from fresh meats and seafood to specialty snacks and ready-to-eat deli items, making it easy to find everything you need under one roof. Their selection includes unique pre-made meals and global flavors for convenient, delicious options.

Trader Joe's

Trader Joe's is renowned for its unique offerings, including artisanal cheeses, seasonal snacks, and specialty produce. The store's creative products, like chili lime cashews and mandarin orange chicken, set it apart from other grocery stores.

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.

Whole Foods Market

Whole Foods Market offers a curated selection of organic produce, artisan breads, exclusive desserts like the Berry Chantilly Cake, and a wide range of local craft beers and specialty cheeses, all with a focus on quality, sustainability, and unique culinary experiences.

Joong Boo Market

Joong Boo Market offers a wide range of authentic Korean and Pan-Asian products, including fresh produce, traditional groceries, and specialty items like kimchi and bulgogi. It also features a snack bar serving dishes like bibimbap and dduk gook.

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.

Trader Joe's

Trader Joe's offers a unique selection of specialty produce, artisanal cheeses, and seasonal snacks that keep shoppers excited year-round. Their creative frozen meals, distinctive chips, and flavorful sauces make everyday groceries feel special and fun.

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.

Bungalow by Middle Brow

Bungalow by Middle Brow offers a unique all-day experience featuring naturally fermented sourdough pizzas, house-brewed beers, and artisanal pastries, all served in a cozy, communal setting that feels like home. Their specialty lies in combining craft brewery, bakery, and pizzeria under one roof.

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.

Select dates in Wander Chicago Sky

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Guests love this place

Guests love the Property, Full kitchen, Large TV and more.
Our stay was above & beyond our expectations from the moment of booking. The attention to detail, gorgeous decor, views , amenities was outstanding. The house feels like home. We are people that appreciate the details of a build and interior design & this house is nothing short of amazing. Highly recommend!
Callie from Cleveland, OH
Callie from Cleveland, OH
Stayed in Oct 2025
Absolutely loved our time here. Felt right at home. Quick and responsive to take care of anything we needed. So helpful with recommendations and accommodations. We will definitely be back many times!
Kate from Houston, TX
Kate from Houston, TX
Stayed in Oct 2025
From the moment I booked, Wander took care of everything. Their recommendations were spot-on, and the location was perfect for my needs. It truly felt like a luxurious escape, stress-free from start to finish.
Emily from Houston, TX
Emily from Houston, TX
Stayed in Oct 2025

Have a question?

24/7 Concierge
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Things to know

Here are some things which you should know before booking Wander Chicago Sky
HOUSE RULES
Check-in: after 4:00 pm
Check-out: before 10:00 am
16 guests maximum
No pets allowed
No smoking - fees will apply
Events require approval
CANCELLATION POLICY
Cancel within 24 hours for a full refund.

Before you book

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Oct 30, 2025$331Available
Oct 31, 2025$720Available
Nov 1, 2025$647Not Available
Nov 2, 2025$240Not Available
Nov 3, 2025$247Not Available
Nov 4, 2025$215Not Available
Nov 5, 2025$216Not Available
Nov 6, 2025$281Not Available
Nov 7, 2025$646Not Available
Nov 8, 2025$652Not Available
Nov 9, 2025$318Not Available
Nov 10, 2025$194Not Available
Nov 11, 2025$182Not Available
Nov 12, 2025$182Available
Nov 13, 2025$214Available
Nov 14, 2025$667Available
Nov 15, 2025$692Not Available
Nov 16, 2025$229Available
Nov 17, 2025$196Available
Nov 18, 2025$199Available
Nov 19, 2025$253Available
Nov 20, 2025$325Available
Nov 21, 2025$805Available
Nov 22, 2025$832Available
Nov 23, 2025$453Available
Nov 24, 2025$386Available
Nov 25, 2025$444Not Available
Nov 26, 2025$681Not Available
Nov 27, 2025$700Not Available
Nov 28, 2025$1032Not Available
Nov 29, 2025$869Available
Nov 30, 2025$251Available
Dec 1, 2025$224Available
Dec 2, 2025$224Available
Dec 3, 2025$353Available
Dec 4, 2025$338Available
Dec 5, 2025$617Available
Dec 6, 2025$599Available
Dec 7, 2025$215Available
Dec 8, 2025$185Available
Dec 9, 2025$182Available
Dec 10, 2025$216Available
Dec 11, 2025$249Available
Dec 12, 2025$733Available
Dec 13, 2025$734Not Available
Dec 14, 2025$446Available
Dec 15, 2025$281Available
Dec 16, 2025$282Available
Dec 17, 2025$327Available
Dec 18, 2025$634Available
Dec 19, 2025$957Available
Dec 20, 2025$986Available
Dec 21, 2025$712Available
Dec 22, 2025$968Available
Dec 23, 2025$1024Available
Dec 24, 2025$1140Available
Dec 25, 2025$1038Available
Dec 26, 2025$1511Available
Dec 27, 2025$1491Available
Dec 28, 2025$1014Available
Dec 29, 2025$1032Available
Dec 30, 2025$1072Available
Dec 31, 2025$1203Available
Jan 1, 2026$673Available
Jan 2, 2026$741Available
Jan 3, 2026$645Available
Jan 4, 2026$227Not Available
Jan 5, 2026$193Not Available
Jan 6, 2026$195Not Available
Jan 7, 2026$200Not Available
Jan 8, 2026$201Available
Jan 9, 2026$420Available
Jan 10, 2026$391Available
Jan 11, 2026$181Available
Jan 12, 2026$167Available
Jan 13, 2026$216Available
Jan 14, 2026$192Available
Jan 15, 2026$226Available
Jan 16, 2026$511Available
Jan 17, 2026$497Available
Jan 18, 2026$299Available
Jan 19, 2026$220Available
Jan 20, 2026$197Available
Jan 21, 2026$215Available
Jan 22, 2026$261Available
Jan 23, 2026$516Available
Jan 24, 2026$505Available
Jan 25, 2026$226Available
Jan 26, 2026$194Available
Jan 27, 2026$200Available
Jan 28, 2026$243Available
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