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Homes
Chicago Vacation Rentals
Arizona Vacation Rentals
Mexico Vacation Rentals
Experiences
Property Management
Book Now
Stay Somewhere That Feels Unforgettable in the Windy City.
From historic Printer’s Row lofts to multi-level Gold Coast retreats with private rooftops, discover design-led Chicago homes built for gathering, celebrating, and living like a local.
4.87 Rating
Airbnb Superhost
164 Reviews
6 Years Managing Properties
Chicago
$300/night
The Plymouth Building: 4-Bedroom Downtown Flat
8
Guest(s)
4
Bed(s)
3
Bath(s)
Chicago
$1000/night
Luxury 4BD Gold Coast Penthouse with Deck & Views
10
Guest(s)
4
Bed(s)
3.5
Bath(s)
Chicago
$250/night
River North 2BD 2BA Retreat with Balcony & Parking
5
Guest(s)
2
Bed(s)
2
Bath(s)
Chicago
$250/night
Plymouth Collection: 3BD 2BA High Floor with Gym
6
Guest(s)
3
Bed(s)
2
Bath(s)
Chicago
$200/night
Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking
4
Guest(s)
2
Bed(s)
2
Bath(s)
Chicago
$150/night
Spacious Chicago Getaway with Balcony and Parking
4
Guest(s)
2
Bed(s)
2
Bath(s)
Chicago
$100/night
Steps from Midway Airport, 2BR 1BA Garden Unit
5
Guest(s)
2
Bed(s)
1
Bath(s)
Chicago
$500/night
Family 7BD Home with Game Rm, Hot Tub, and Sauna
16
Guest(s)
7
Bed(s)
4.5
Bath(s)
Chicago
$300/night
The Plymouth Building: 4-Bedroom Historic Apartment
8
Guest(s)
4
Bed(s)
3
Bath(s)
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Where to Stay?
Arizona
- Phoenix
- Scottsdale
Baja California Sur
- Palmilla
- San José del Cabo
California
Emigrant
Florida
Illinois
- Chicago
- Forest Park
- Skokie
- Spring Grove
Indiana
- Jeffersonville
Largo
Lusby
Maryland
Minnesota
- Minneapolis
- Saint Paul
Missouri
- Kansas City
Montana
Nekoosa
Port Republic
Scotland
Solomons
South Dakota
Spearfish
Tarpon Springs
Texas
- Austin
- Houston
Arrive
Depart
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Clear
Done
Guests
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Adults
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Advanced
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Amenities
Accessible-height toilet
Air conditioning
Baby monitor
Baking sheet
Balcony
Barbeque utensils
Bathtub
BBQ grill
Beach
Beach access
Beach essentials
Beach Front
Beach View
Bed linens
Bikes
Blender
Board games
Boat slip
Body soap
Breakfast
Cable TV
Carbon monoxide detector
Casinos
Ceiling fan
Children’s books and toys
Children’s dinnerware
City View
Cleaning before checkout
Cleaning Disinfection
Cleaning products
Clothing storage
Coffee
Coffee maker
Coin Laundry
Communal pool
Conditioner
Cookware
Crib
Cycling
Desert View
Desk
Dining table
Disabled parking spot
Dishes and silverware
Dishwasher
Doorman
Downtown
Dryer
Dryer in common space
Dvd player
Elevator
Emergency exit
Enhanced cleaning practices
Essentials
EV charger
Extra pillows and blankets
Family/kid friendly
Fire extinguisher
Fire Pit
Fireplace guards
First aid kit
Fishing
Foosball table
Free parking on premises
Free parking on street
Freezer
Game console
Game room
Garage
Garden or backyard
Garden View
Golf - Optional
Golf course front
Golf view
Grab-rails for shower and toilet
Gym
Hair dryer
Hammock
Hangers
Heating
High chair
High touch surfaces disinfected
Horseback Riding
Hot tub
Hot water
Ice maker
Indoor fireplace
Internet
Iron
Kayak
Kettle
Kitchen
Lake
Lake access
Lake Front
Laptop friendly workspace
Laundromat nearby
Long term stays allowed
Luggage dropoff allowed
Microwave
Mini fridge
Mountain
Mountain Climbing
Mountain view
Museums
Near Ocean
Ocean Front
Outdoor kitchen
Outdoor pool
Outdoor seating (furniture)
Outlet covers
Oven
Pack ’n Play/travel crib
Paid parking
Paid parking off premises
Path to entrance lit at night
Patio or balcony
Pets allowed
Piano
Ping pong table
Pocket wifi
Pool table
Portable fans
Private entrance
Private pool
Refrigerator
Resort access
Rice maker
River
Rock Climbing
Rooftop pool
Room-darkening shades
Rural
Safe
Sauna
Sea view
Shampoo
Shopping
Shower gel
Single level home
Smoke detector
Smoking allowed
Sound system
Spa
Stair gates
Step-free access
Stereo system
Stove
Suitable for children (2-12 years)
Suitable for events
Suitable for infants (under 2 years)
Swimming pool
Tennis court
Theme Parks
Toaster
Towels provided
Town
Trash compactor
Tub with shower bench
TV
Village
Washer
Washer in common space
Water Parks
Water Sports
Water View
Waterfront
Wheelchair accessible
Wide clearance to bed
Wide clearance to shower and toilet
Wide doorway
Wide hallway clearance
Window guards
Wine glasses
Wireless Internet
Zoo
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Luxury Chicago Vacation Rentals & Group Stays
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