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
Newly Updated Nashville Home
4 BR • 2 BA • Sleeps 12Nashville, Tennessee

This completely updated 4BD/2BA Nashville home (sleeps 12) is a short walk to dining in the hip Five Points neighborhood, and a quick dri...

Lavish Home w/ Amazing Rooftop Deck
3 BR • 3.5 BA • Sleeps 10Nashville, Tennessee

The excitement of Nashville beckons, and this brand-new 3BR, 3.5BA townhouse is the perfect home base.

Rooftop Deck with Downtown Views
3 BR • 3.5 BA • Sleeps 9Nashville, Tennessee

Live like a rock star in this 3BR/3.5BA Nashville townhouse just minutes from the music, culture, and fun of downtown and hip neighborhoo...

Character & Charm in East Nashville
4 BR • 3.5 BA • Sleeps 12Nashville, Tennessee

An elegant Nashville vacation rental in a picturesque, tree-lined neighborhood three miles from downtown!


All Chicago Rentals
2BR Modern Ukrainian Village Condo

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.

TurnKey Popular Destinations
TurnKey Vacation Rental Markets
New Mexico