DATES
SEARCH ALL CHICAGO RENTALS
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.
Top Chicago vacation rentals for large groups
Top Chicago vacation rentals for large groups
Guest-favorite Chicago vacation homes
View all top-rated Chicago homes
New TurnKey homes in Chicago
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
What makes the TurnKey experience different from listing sites like Airbnb, Vrbo and HomeAway?
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.
How is TurnKey responding to COVID-19?
In response to the COVID-19 outbreak, TurnKey has enhanced its already extensive home cleaning standards and processes to further sanitize homes between each stay for our guests and owners. All TurnKey properties are equipped with our patented GuestWorks® cleaning system and verification technology, requiring professional housekeepers to follow a stringent set of cleaning standards, customized for each home, and confirm their use of COVID-19 fighting products, as identified by the Center for Biocide Chemistries. We have also emphasized effective hygiene practices and safety recommendations for our employees and housekeeping network in line with CDC guidelines. In addition, we have initiated the TurnKey Cares Relief Housing Program, offering thousands of homes for medical personnel and first-responders at complimentary or significantly discounted rates while they perform critical services to fight COVID-19.
Do you offer special rates and availability for long-term stays?
Yes. Many TurnKey homes allow for special rates for monthly or long-term stays. In addition, while booking calendars may appear blocked due to local orders, many of our properties have exclusive availability for medical personnel and first-responders who need a place to stay while performing critical services to fight COVID-19. To inquire about the special monthly rates or exclusive availability, please call us at 888-512-0498.
Will the home be clean when I arrive?
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.
Do I have to clean up before I leave?
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.
Who do I contact if I need support?
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.
Do the homes have WiFi?
All of TurnKey’s Chicago vacation rentals are equipped with complimentary, reliable, high-speed WiFi so you can always stay connected.
Is there a kitchen where I can prepare meals?
Every TurnKey Chicago vacation rental includes a fully-equipped kitchen where you can cook and prepare meals with your friends and family.
How do I check in?
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.
What makes TurnKey’s Chicago homes different?
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.