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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 Wicker Park Coach House
$150
FROM
2 BR • 2 BA • Sleeps 4Chicago, Illinois

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

#1406451
Lakeview 2BR w/ Private Patio
$130
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
Lincoln Park 2BR - Walk Everywhere!
$240
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 Modern Ukrainian Village Condo
$210
FROM
2 BR • 2.5 BA • Sleeps 6Chicago, Illinois

PROPERTY OVERVIEW Situated in a quintessential brick row house in the trendy Ukrainian Village sits this two-story 2BR/2.5BA condo.

#1316986

All Chicago Rentals
2BR Modern Ukrainian Village Condo
$210
FROM

2 BR • 2.5 BA • Sleeps 6Chicago, Illinois

PROPERTY OVERVIEW Situated in a quintessential brick row house in the trendy Ukrainian Village sits this two-story 2BR/2.5BA condo.

#1316986
Lakeview 2BR w/ Private Patio
$130
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
$150
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!
$240
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
TurnKey Popular Destinations
TurnKey Vacation Rental Markets
Arizona
Illinois
Massachusetts
New Mexico