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Chicago, IL Vacation Rentals

Welcome to TurnKey Chicago!

The windy city is famed for its bold architecture, prestigious dining scene, the variety of museums, and festive events that take place year round. Stay in a high rise downtown or cozy up in a quaint brownstone in one of the Chicago’s many unique neighborhoods. Regardless of where you stay, you can easily curate your trip to align with your interests.

Every Stay Includes
Complimentary Wi-Fi
Secure keyless entry
Professional cleaning
24/7 local support
Hotel-grade linens
Starter set of toiletries
Local recommendations
Local Chicago Manager
John Janco is a hospitality leader with over 30 years experience in sales and operations for many prestigious brands including Hilton and IHG. John was born and raised in Chicago and lives a few blocks from Wrigley Field in his hometown.



Featured Chicago Rentals
2BR Near Hyde Park, Walk to Lake
$120
FROM
2 BR • 2 BA • Sleeps 6Chicago, Illinois

Located on the outskirts of Hyde Park, this 2BR/2BA condo is perfect for a cultural weekend in Chicago.

#1459463
Lincoln Park 2BR - Walk Everywhere!
$120
FROM
2 BR • 2 BA • Sleeps 6Chicago, Illinois

Just a 5-minute walk from the North/Clybourn Red Line station, this beautifully decorated 2BR/2BA Lincoln Park condo is the perfect home...

#1408484
4827NRAB
$190
FROM
4 BR • 3.5 BA • Sleeps 8Chicago, Illinois

THE TURNKEY ADVANTAGE Our property is TurnKey Rental Certified. All photos, amenities, calendar, and rates are 100% accurate.

#1466097
Lakeview 2BR w/ Private Patio
$120
FROM
2 BR • 2.5 BA • Sleeps 6Chicago, Illinois

PROPERTY OVERVIEW This 2BR/2.5BA townhouse affords a great Lakeview location with quick access to public transportation and a plethora o...

#1369377

All Chicago Rentals
Lakeview 2BR w/ Private Patio
$120
FROM

2 BR • 2.5 BA • Sleeps 6Chicago, Illinois

PROPERTY OVERVIEW This 2BR/2.5BA townhouse affords a great Lakeview location with quick access to public transportation and a plethora o...

#1369377
2BR Wicker Park Coach House
$130
FROM

2 BR • 2 BA • Sleeps 4Chicago, Illinois

Enjoy the historic charm of coach-house living at this completely renovated 2BR/2BA condo.

#1406451
Lincoln Park 2BR - Walk Everywhere!
$120
FROM

2 BR • 2 BA • Sleeps 6Chicago, Illinois

Just a 5-minute walk from the North/Clybourn Red Line station, this beautifully decorated 2BR/2BA Lincoln Park condo is the perfect home...

#1408484
2BR Near Hyde Park, Walk to Lake
$120
FROM

2 BR • 2 BA • Sleeps 6Chicago, Illinois

Located on the outskirts of Hyde Park, this 2BR/2BA condo is perfect for a cultural weekend in Chicago.

#1459463
4827NRAB
$190
FROM

4 BR • 3.5 BA • Sleeps 8Chicago, Illinois

THE TURNKEY ADVANTAGE Our property is TurnKey Rental Certified. All photos, amenities, calendar, and rates are 100% accurate.

#1466097
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