Exceptional Chicago, IL Vacation Rentals | TurnKey

Exceptional Chicago Vacation Rentals

Every Home. Every Stay. Every Time.℠

Professionally cleaned before every stay
24/7 local in-market support
100% up-to-date booking calendars
Automated secure home access

Why Chicago guests love staying with TurnKey...

"We loved the Lakeview property. Every amenity was available and the house was spacious, gave us plenty of room to be comfortable. Plus a garage for our car. It was convenient as well, close to public transportation, loads of small restaurants and stores nearby. Easy to reach all Chicago’s attractions - downtown, Wrigley, Lake Michigan, etc."..."
Nancy M. 9 days ago
Family Friendly Lakeview 2BR w/ Private Patio
"Everything was clean,and was bigger than expected."..."
Shakera R. about 2 months ago
Cozy 5BR Near Jackson Park, Hyde Park & Metra Line
"Located a very short walk from the Blue line, this unit is in a quiet residential neighborhood. The beds are comfortable and the unit is well equipped. We would stay here again."..."
Chicago TurnKey Guest 2 months ago
Garden-Level Apartment w/ Yard, 4-minute Walk to Metro
"Cool rental. Clean and functional. Property managers were very professional."..."
Ricardo P. 3 months ago
Vertical Living w/ Rooftop Deck & Skyline Views!
Every Home. Every Stay. Every Time.
Professional Cleaning
Hotel quality linens
Starter set of toiletries
Complimentary Wi-Fi
Secure, keyless entry
24/7 local support

Local Chicago Support Team

With support from our local, Chicago team, you can relax and focus on creating one-of-a-kind vacation memories. We’re standing by 24/7 to make sure you experience the smarter way to vacation rental.

24/7 guest support

The TurnKey Promise

Every Home. Every Stay. Every Time.℠ That’s the TurnKey promise. With TurnKey Vacation Rentals, you’ll always find unique vacation rental properties with a consistent, fine-hotel experience.

We guarantee all listing information is accurate and up to date. Upon booking, you’ll be provided timely and helpful communications regarding your trip. If you need anything before, during, or after your stay, our 24/7 local team is ready to help!

At TurnKey properties, 90% of guest reviews are 4-5 stars, and we maintain a 93% guest satisfaction rating of cleanliness upon check in. And don’t worry … you’ll never have to clean up after your stay.

Selecting a TurnKey property, you can truly relax and know you’ve made the right vacation rental decision for your travel needs. TurnKey is truly the smarter way to vacation rental.℠

Why rent a vacation home in Chicago, IL

The City of Big Shoulders needs no introduction: towering skyscrapers, incredible architecture, world-famous shopping, dining, and entertainment, fantastic festivals, unparalleled museums, a sports culture envied the world-over -- you know why you’re here. If you are planning a trip to the Windy City, consider renting a vacation home. Vacation rentals offer numerous advantages over traditional hotel accommodation, particularly for those traveling as a group. Families and groups will appreciate the extra space you’ll have in more vacation rentals, whether they’re spending quality time together in the living room or preparing shared meals in the full kitchen. Renting a vacation home can also make for a more authentic experience, and allows you to get to know Chicago’s fantastic and varied neighborhoods: you might soon feel like you’re a resident of West Town or Lincoln Park too. And when you stay in a TurnKey Chicago rental, you don’t have to fret losing out on your favorite hotel perks: each and every one of our homes includes free WiFi, a starter set of toiletries, hotel-grade towels and linens, is professionally cleaned prior to your arrival, and 24/7 support from our local Chicago team. It’s the best of both worlds.

Here are some things you can look forward to during your stay in a Chicago vacation rental:

  • Navy PierNavy Pier is one of the most recognizable landmarks in Chicago, and has a rich history of playing an important role in the city. Originally built as a home for passenger and freight docks in 1916, the pier went on to serve as a location for housing soldiers during World War 1. Today, it’s an iconic landmark with a ferris wheel, an IMAX theatre, dining options, events spaces, and a convention center.
  • Architecture Boat ToursWhile most people will say the best architectural experience in Chicago is standing in the overhanging glass boxes at the top of Willis Tower, we suggest you consider hopping on an architecture boat tour. Most boat tours depart from the Michigan Avenue bridge in the heart of downtown, and take passengers on an engaging tour of the history and stories behind the city’s most iconic landmarks and buildings.
  • Music and ComedyFestivals like Lollapalooza and Pitchfork draw thousands of visitors to the city every summer. Typically taking place in the beautiful parks around Chicago, festivals are a great way to catch many of your favorite bands in one place. If you love music but not crowds, consider visiting world-class venues like Green Mill for jazz or The Chicago Theatre. For laughs, buy tickets to see one of the hilarious comedy troupes at The Second City, famous for training and showcasing some of today’s most prominent comedians.
  • Dining and ShoppingThe Chicago restaurant scene is a food lover’s dream. The ever evolving landscape offers every type of cuisine your heart could desire, from juicy steaks to class hot dogs (no ketchup allowed!). Whichever area you stay, be that downtown or a neighborhood, there’s bound to be an amazing restaurant near you. There’s also a plethora of shopping in Chicago. Window shop designer luxuries along Michigan Avenue (also known as the Mag Mile), or peruse designer and local boutiques in neighborhoods like Lincoln Park and Wicker Park.
  • MuseumsChicago is home to some of the most famous artwork and artifacts in the world. Spend hours getting lost in the art at The Art Institute, explore through history at The Field Museum of Natural History, or go underwater at the Shedd Aquarium.
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