The Theatre District in Chicago is a vibrant cultural hub that beckons both enthusiasts and newcomers alike. Nestled in the heart of the city, it boasts a rich history and a plethora of entertainment options. If you are seeking an immersive experience, you can join some of the tours in Chicago offering a fascinating glimpse into the district’s storied past, highlighting iconic venues and legendary performances. Beyond the stage, the Theatre District is abuzz with a calendar brimming with events and festivals, promising an electrifying atmosphere year-round. From Broadway blockbusters to avant-garde productions, this district pulsates with creativity, ensuring every visitor a theatrical experience they won’t soon forget. So keep reading to explore some of the best Vrbo vacation rentals in Chicago’s Theater District, Illinois!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 08, 2024.
1. Stylish home with a rooftop deck (from USD 375)
Discover a stunning home at this condo in the Theatre District that features huge windows bringing in ample natural light making the space bright. The home offers stunning views of the city skyline. The living room features comfortable loungers and dining space, as well as a television for entertainment.
The well-appointed bedrooms and bathrooms are stocked with basic essentials such as bath products, towels, bed linens and more. The kitchen is equipped with modern appliances and the rooftop deck is the ideal place to relax after a day of exploration.
2. Stunning penthouse with lake views (from USD 525)
Experience a luxurious getaway at this stylish and thoughtfully decorated penthouse with a cosy living room that features an indoor fireplace. Unwind in its warmth while admiring the beautiful city views from the huge window adjacent to the lounger. The kitchen is spacious with a huge island and modern appliances which encourage culinary exploration.
The bedrooms are spacious with plush mattresses and the bathrooms feature a shower and premium cleaning products to ensure a comfortable retreat. Guests can access the rooftop deck to enjoy the beautiful Chicago sunsets.
Top guest reviews
Cleanliness:
the apartment was very nice and cleanfirst time i go to chicago the penthouse is beautiful clean i liked it a lot and my familyHost:
host was extremely easy to communicate with and accommodatingthe communication with the owner was excellent highly recommendedRead more reviewsLocation:
great location in the middle of downtown chicagoamazing location couldn’t beat itthis property was in a great locationgreat location but you really need to fix the plumbinggreat location close to lots of shopping the theater great food and all the museums and parks
3. Pet-friendly apartment with a pool (from USD 500)
This downtown Chicago home offers essential amenities including wireless internet, plush linens, and a fully equipped kitchen. The cosy living room is the ideal spot to relax and unwind at the end of an adventurous day around the city. It boasts a prime location with a stunning lake view and easy access to an outdoor pool.
The building is equipped with an elevator, making it convenient for all guests. Whether you’re here for business or leisure, this home provides a comfortable and centrally located retreat in the heart of the city. It is also within walking distance of some of the best restaurants in Chicago’s Theatre District.
4. Charming and modern three-bedroom stay with incredible pier views (from USD 785)
You can always tell when a home has been professionally decorated! With modern yet charming furniture and decor, luxury bedding and elegant upholstery, and exquisite features that will make you never want to leave, this place to stay in downtown Chicago is one of the best that you can get.
Spoil yourself with a myriad of decadent amenities at your disposal, including a fully equipped kitchen to experiment with meals in, a flat-screen television, spacious walk-in closets so you need not live out of your suitcase, luxurious bathrooms with complimentary toiletries and beauty gadgets, and more.
Step out into the complex to find another set of amenities waiting to be used, such as an indoor pool with skylights, a sundeck that includes firepits, grilling stations, private cabanas with flat-screen televisions, a fitness centre, a cyber cafe, and a hot tub. You are sure to extend your stay here just to take advantage of everything this home has to offer!
Top guest reviews
Amenities & Room:
The bedrooms are spacious with comfortable beddingThe apartment was as describedHad an amazing experience in Chicago over the weekend doing Christmas shopping and fine diningyou wonder if it REALLY will be anything like thatThe rental was extremely clean and the pictures do not do the rental justice on just how spacious it is more then enough room for my group of 5Host:
Great family weekend with my wife and 3 kids Didn't even consider driving anywhere once we arrivedAnd most of all the host was very Nice Thoughtful and GenerousGreat views Easy to work with CleanGreat property with fantastic customer serviceOverall our family enjoyed the rentalRead more reviewsLocation:
Me and my group loved our stay from the easy parking right around the corner to all the restaurants in walking distanceThere is so much to do and see from this great central location and every type of restaurant imaginable nearbyIt went above and beyond what was advertised A perfect place to stay in Chicago Walking distance to everywhere we wanted to goconvenient on-site parking with in/out access (need to pay extra $60 per day)Great location clean and easy to come and go
5. Beautiful views from this three-bedroom gorgeous accommodation (from USD 775)
This Vrbo accommodation in downtown Chicago is perfect for those who want to vacation in style. From the moment you step into this three-bedroom unit, you are taken into another world altogether. With all the luxuries of a hotel room, this home offers elegant furnishings and linen, wood floors, indoor and outdoor pool open year-round, cabanas, a fire pit, and grills if you wish to have a meal outdoors while watching the stars, and an outdoor lounge to relax in.
In addition to the above, this home does not compromise on the comforts and amenities you can get in your own home, with a fully equipped gourmet kitchen with all the necessary cookware and gadgets you need to make your own delicious homemade meals, three cosy bedrooms with a king-sized and two queen-sized beds, high-speed internet, washer and dryer facility so you can pack light and more! Lastly, don’t miss the breathtaking skyscraper views!
Top guest reviews
Amenities & Room:
needed more living room seating and a tv in every bedroomthe pool was large and warmcozy and comfortable home away from homethe only challenge we had was with the air in one of the rooms not workingdisappointed that there was very little toilet paper, a few paper towels and one partial box of kleenexCleanliness:
very clean andcan't beat the locationwe didn't cook but did use the coffee pot and washer and dryerthe condo and building are full of amenitiesalso expected luxurious bathrooms and they were very basicHost:
anthony and his concierge team are incredibly helpful and super responsive! we cannot wait to stay again!!all worked greatwe stayed here for a girls weekend and could not have been happier!! anthony and his concierge were very responsive and everything about the stay was simple, including the arrival and departure pro...came in handy for people who didn't want to sleep in the same bedawesome viewsRead more reviewsLocation:
it was too late to select another locationit's in a nice neighborhood with markets and restaurants easily in walking distancewe enjoyed the nearby restaurantsvery convient locationresidents have to go through the pool area to take their dogs out to the condo's dog area
6. Grand three-bedroom apartment with stunning views (from USD 675)
Centrally located in downtown/West Loop Chicago, this beautiful luxury home offers stunning skyscraper views from every room and floor-to-ceiling French windows. The home is about 1500 square foot (139 square meters) and can comfortably accommodate up to six people. It includes a master bedroom with an attached large bath and double sinks and a shower, and two other private bedrooms. All the bedrooms have queen-sized beds with down comforters and pillows for your comfort. There is also an attached garage, a living room with LCD television, a dining room with a four-person table, and an eat-in gourmet chef’s kitchen with all the cookware and gadgets you need. This home promises a luxurious time whether you are alone or with family.
Top guest reviews
Amenities & Room:
The clean modern apartment was well equipped and provided excellent views of the cityThe space worked fine for ushave our own bedroom and bathroom but still be able to hang out togetherThe only quibble we had was there were no tea towels to dry dishes withdecor beds are so comfyCleanliness:
The place was very clean with terrific viewsHost:
Michelle was a fantastic hostess happy to respond to texts of any sort--The owner was very accommodating and made our arrival and departure easy and convenientwhere to find more garbage bags even met us when we arrived to show keysThe apartment is very well stocked and Michelle our hostess was very gracious Definitely would stay againso we could hang out in the television areaRead more reviewsLocation:
Great location and great property Only a 20 minute walk to downtown and many great restaurants within a 5 minute walkThe local area is populated by restaurantsThe neighborhood here was very safe and jam-packed with restaurants/bars even just across the street on every corner A short walk to the Metra stationThe property was located in a great neighborhood with many excellent cafes and restaurantsUber ride to downtown attractions
Welcome to the home of theatre in Chicago
Instead of booking a crowded hotel with constant supervision and crowds, imagine retreating into your very own home away from home, as you book one of our Vrbo accommodations and make Chicago your home, even if it’s just for a few days. No matter what your budget may be, Chicago has something breathtakingly awesome for you. For solo travellers and couples, there are many room rentals in the Chicago Theatre District. So start booking your vacation now!
Frequently asked questions about Vrbo vacation rentals in Chicago's Theater District, Illinois
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