Exceptional Chicago, IL Vacation Rentals | TurnKey

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In partnership with our homeowners, TurnKey is offering thousands of homes for COVID-19 responders at heavily discounted rates for housing needs through May 31, 2020. We thank you for your service and look forward to helping you during this unprecedented time.

Exceptional Chicago Vacation Rentals

Every Home. Every Stay. Every Time.℠

Why TurnKey is the smarter way to vacation rental

Distinctive Homes

Discover our collection of luxury and premium properties in top destinations across the U.S.

Professionally Cleaned

Enjoy a spotless home with fresh, hotel-grade linens and a starter set of toiletries.

Full Kitchens

Prepare meals for family and friends in fully equipped kitchens.

24/7 Guest Support

Contact our team at any time to help make your stay more enjoyable.

Complimentary Wi-Fi

Entertain or work with reliable high-speed Wi-Fi in every TurnKey home.

Seamless Check-In

Access each home with clear arrival instructions and easy-to-use digital locks.

Why Chicago guests love staying with TurnKey...

"We loved this townhouse! It was close to public transportation but also great to have a garage for our car. The house had all the amenities we needed and loads of room, space for us to spread out and be comfortable. We could get to anywhere we wanted to go quickly - downtown, the lake, Lincoln Park, Wrigley field, shopping! The mgmt company was very responsive and available to us. I would recommend this rental to anyone."..."
Chicago TurnKey Guest 6 months ago
Family Friendly Lakeview 2BR w/ Private Patio
"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. 7 months ago
Family Friendly Lakeview 2BR w/ Private Patio
"Everything was clean,and was bigger than expected."..."
Shakera R. 8 months ago
"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 9 months ago
Garden-Level Apartment w/ Yard, 4-minute Walk to Metro

Top Chicago vacation rentals for large groups

Stylish Downtown High-Rise: City Views, Pool & Gym
1 BR 1 BA Sleeps 2
New#1614155
Enjoy breathtaking views of downtown Chicago from this stylish, 23rd-floor condo.
From $80/night
Top Chicago vacation rentals for large groups

Top Chicago vacation rentals for large groups

Guest-favorite Chicago vacation homes

Stylish Downtown High-Rise: City Views, Pool & Gym
1 BR 1 BA Sleeps 2
New#1614155
Enjoy breathtaking views of downtown Chicago from this stylish, 23rd-floor condo.
From $80/night
View all top-rated Chicago homes

View all top-rated Chicago homes

New TurnKey homes in Chicago

Stylish Downtown High-Rise: City Views, Pool & Gym
1 BR 1 BA Sleeps 2
New#1614155
Enjoy breathtaking views of downtown Chicago from this stylish, 23rd-floor condo.
From $80/night
View the newest Chicago TurnKey homes

View the newest Chicago TurnKey homes

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.

Chicago Vacation Rentals Frequently Asked Questions

Companies like Airbnb and Vrbo operate listing websites that enable guests to research and book a vacation rental anywhere in the world. However, once a guest books the property, they need to work directly with either the homeowner, host or property manager any time they have questions or need assistance with booking or during their stay. This can be a challenge for some homeowners, particularly those who live far away from their vacation rental. TurnKey offers a consistent and reliable high-end experience, resulting in strong reviews, repeat bookings and more. TurnKey also has a local Chicago team, 24/7 support and in-home technology to ensure an amazing vacation experience in every home, every stay, every time.

Yes! TurnKey has established the best network of professional house cleaners in Chicago to ensure that our guests always arrive at an exceptionally clean home. Expect to find beds made with hotel-grade linens and bathrooms stocked with fresh towels and a complimentary starter set of toiletries.

Unlike many vacation rentals in the area, our local team and network of Chicago house cleaners guarantee that you’ll never need to clean up at the end of your stay. Sometimes, especially during busy seasons, starting a load of towels or linens can help our house cleaners finish their clean more quickly. We certainly appreciate it when guests do this, but we do not require it.

TurnKey offers 24/7 guest support that you can contact at any time to make your stay more enjoyable. Paired with our local Chicago team, we can respond quickly to any in-home help you might need.

All of TurnKey’s Chicago vacation rentals are equipped with complimentary, reliable, high-speed WiFi so you can always stay connected.

Every TurnKey Chicago vacation rental includes a fully-equipped kitchen where you can cook and prepare meals with your friends and family.

We’ve installed our proprietary digital locks on all Chicago vacation rentals to offer our guests secure, keyless entry. Each code is time-sensitive, so you don’t have to worry about anyone else having access to the home while you’re there. Prior to check-in, you’ll receive arrival instructions with your custom code for easy, seamless access.

TurnKey carefully vets all of our homes, so you can be sure you’ll always stay in a premium vacation rental. We offer some of the most distinctive, unique vacation homes in all of Chicago, backed by our exceptional home care and 24/7 guest service.

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