Wander Chicago Sky
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16 guests
7 beds
4 bathrooms
Game Room•Hot tub•Sauna
16 guests
5 bedrooms
7 beds
4 bathrooms
4500 sq. ft.
Wander Chicago Sky is an opulent urban escape offering unparalleled luxury and recreation.
The Wander Guarantee
Book with confidence. Read more.
Flexible check-in & out
Check-in after 4:00pm • Check-out before 10:00am • No 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
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
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.
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.
Select dates in Wander Chicago Sky
Choose your check-in & check-out dates
4.7
based on 52 reviews
Guests love the rooftop, hot tub and game room with ping pong and arcade machines. They praise the great location near transit and restaurants, the spotless spacious layout for large groups, and the host's responsiveness that quickly fixes any issues.
Have a question?
24/7 Concierge
Chat with Concierge
Talk with the concierge to ask any question you might have
Things to know
Here are some things which you should know before booking Wander Chicago Sky
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
Cancel within 24 hours for a full refund.
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
Before you book
Availability & Pricing
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Dec 14, 2025 | $432 | Not Available |
| Dec 15, 2025 | $305 | Not Available |
| Dec 16, 2025 | $305 | Not Available |
| Dec 17, 2025 | $267 | Available |
| Dec 18, 2025 | $390 | Available |
| Dec 19, 2025 | $897 | Available |
| Dec 20, 2025 | $948 | Not Available |
| Dec 21, 2025 | $571 | Not Available |
| Dec 22, 2025 | $755 | Not Available |
| Dec 23, 2025 | $827 | Not Available |
| Dec 24, 2025 | $998 | Not Available |
| Dec 25, 2025 | $968 | Not Available |
| Dec 26, 2025 | $1280 | Not Available |
| Dec 27, 2025 | $1234 | Not Available |
| Dec 28, 2025 | $781 | Not Available |
| Dec 29, 2025 | $861 | Not Available |
| Dec 30, 2025 | $836 | Not Available |
| Dec 31, 2025 | $1031 | Not Available |
| Jan 1, 2026 | $556 | Not Available |
| Jan 2, 2026 | $758 | Not Available |
| Jan 3, 2026 | $610 | Not Available |
| Jan 4, 2026 | $252 | Not Available |
| Jan 5, 2026 | $234 | Not Available |
| Jan 6, 2026 | $234 | Not Available |
| Jan 7, 2026 | $233 | Not Available |
| Jan 8, 2026 | $256 | Not Available |
| Jan 9, 2026 | $508 | Not Available |
| Jan 10, 2026 | $472 | Not Available |
| Jan 11, 2026 | $166 | Available |
| Jan 12, 2026 | $163 | Available |
| Jan 13, 2026 | $157 | Available |
| Jan 14, 2026 | $239 | Available |
| Jan 15, 2026 | $276 | Not Available |
| Jan 16, 2026 | $571 | Not Available |
| Jan 17, 2026 | $564 | Not Available |
| Jan 18, 2026 | $329 | Not Available |
| Jan 19, 2026 | $184 | Available |
| Jan 20, 2026 | $185 | Available |
| Jan 21, 2026 | $216 | Available |
| Jan 22, 2026 | $246 | Available |
| Jan 23, 2026 | $571 | Available |
| Jan 24, 2026 | $559 | Not Available |
| Jan 25, 2026 | $240 | Available |
| Jan 26, 2026 | $213 | Available |
| Jan 27, 2026 | $217 | Available |
| Jan 28, 2026 | $244 | Available |
| Jan 29, 2026 | $271 | Available |
| Jan 30, 2026 | $526 | Available |
| Jan 31, 2026 | $537 | Not Available |
| Feb 1, 2026 | $238 | Not Available |
| Feb 2, 2026 | $152 | Available |
| Feb 3, 2026 | $152 | Available |
| Feb 4, 2026 | $258 | Available |
| Feb 5, 2026 | $291 | Not Available |
| Feb 6, 2026 | $557 | Available |
| Feb 7, 2026 | $610 | Available |
| Feb 8, 2026 | $274 | Available |
| Feb 9, 2026 | $214 | Available |
| Feb 10, 2026 | $215 | Available |
| Feb 11, 2026 | $248 | Available |
| Feb 12, 2026 | $254 | Available |
| Feb 13, 2026 | $573 | Available |
| Feb 14, 2026 | $570 | Not Available |
| Feb 15, 2026 | $262 | Available |
| Feb 16, 2026 | $227 | Available |
| Feb 17, 2026 | $180 | Available |
| Feb 18, 2026 | $253 | Available |
| Feb 19, 2026 | $314 | Available |
| Feb 20, 2026 | $636 | Not Available |
| Feb 21, 2026 | $644 | Not Available |
| Feb 22, 2026 | $270 | Available |
| Feb 23, 2026 | $268 | Available |
| Feb 24, 2026 | $261 | Available |
| Feb 25, 2026 | $287 | Available |
| Feb 26, 2026 | $300 | Available |
| Feb 27, 2026 | $641 | Available |
| Feb 28, 2026 | $646 | Not Available |
| Mar 1, 2026 | $362 | Available |
| Mar 2, 2026 | $350 | Available |
| Mar 3, 2026 | $335 | Available |
| Mar 4, 2026 | $378 | Available |
| Mar 5, 2026 | $505 | Available |
| Mar 6, 2026 | $1121 | Available |
| Mar 7, 2026 | $1134 | Available |
| Mar 8, 2026 | $407 | Available |
| Mar 9, 2026 | $355 | Available |
| Mar 10, 2026 | $351 | Available |
| Mar 11, 2026 | $496 | Available |
| Mar 12, 2026 | $695 | Available |
| Mar 13, 2026 | $1825 | Available |
| Mar 14, 2026 | $1814 | Available |