4 Best Vrbo Vacation Rentals In Chicago's Theater District, Illinois


Whether you are new to the theatre scene or you’ve been a theatre enthusiast for years, Chicago’s Theatre District is the place to be if you wish to get a taste of some of the best shows available anywhere. Similar to New York City’s Broadway, Chicago’s Theatre District is a hub of tourist attractions as well. From lip-smacking cuisines from around the world in one of the many Michelin Star restaurants this city has to boast about, to relaxing cafes for caffeine addicts, to vivid and dynamic nightlife where you can de-stress on the dance floor, Chicago’s Theatre District is a fun-filled urban adventure that you will never want to end. So keep reading as we explore some of the best Vrbo accommodations in Chicago’s Theater District, Illinois so you can start planning a vacation here as soon as possible!

1. 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 lovely home has all the signs of an attentively and lavishly decorated home. 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 center, 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!

3B/3BA Luxury Navy Pier Corner Sky Loft with Pool & Gym
52 reviews  Wifi Available
Apartment 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
The bedrooms are spacious with comfortable bedding
The apartment was as described
Had an amazing experience in Chicago over the weekend doing Christmas shopping and fine dining
you wonder if it REALLY will be anything like that
The 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 5
Great family weekend with my wife and 3 kids Didn't even consider driving anywhere once we arrived
And most of all the host was very Nice Thoughtful and Generous
Great views Easy to work with Clean
Great property with fantastic customer service
Overall our family enjoyed the rental
Me and my group loved our stay from the easy parking right around the corner to all the restaurants in walking distance
There is so much to do and see from this great central location and every type of restaurant imaginable nearby
It went above and beyond what was advertised A perfect place to stay in Chicago Walking distance to everywhere we wanted to go
convenient on-site parking with in/out access (need to pay extra $60 per day)
Great location clean and easy to come and go
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2. Beautiful views from this three-bedroom gorgeous accommodation (from USD 775)

This is a truly appealing retreat for a vacation to Chicago. 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 firepit, 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 cozy 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!

3B/3BA Luxury Penthouse | Amazng Views, Pool & Gym
29 reviews  Wifi Available
Apartment 8 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
needed more living room seating and a tv in every bedroom
the pool was large and warm
cozy and comfortable home away from home
the only challenge we had was with the air in one of the rooms not working
disappointed that there was very little toilet paper, a few paper towels and one partial box of kleenex
very clean and
can't beat the location
we didn't cook but did use the coffee pot and washer and dryer
the condo and building are full of amenities
also expected luxurious bathrooms and they were very basic
anthony and his concierge team are incredibly helpful and super responsive! we cannot wait to stay again!!
all worked great
we 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 bed
awesome views
it was too late to select another location
it's in a nice neighborhood with markets and restaurants easily in walking distance
we enjoyed the nearby restaurants
very convient location
residents have to go through the pool area to take their dogs out to the condo's dog area
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3. 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.

Luxury 3Bed/2.5Bath Apt w/Million Dollar Skyline Views! Garage Parking Included!
60 reviews  Wifi Available
Apartment 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
The clean modern apartment was well equipped and provided excellent views of the city
The space worked fine for us
have our own bedroom and bathroom but still be able to hang out together
The only quibble we had was there were no tea towels to dry dishes with
decor beds are so comfy
The place was very clean with terrific views
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 convenient
where to find more garbage bags even met us when we arrived to show keys
The apartment is very well stocked and Michelle our hostess was very gracious Definitely would stay again
so we could hang out in the television area
Great location and great property Only a 20 minute walk to downtown and many great restaurants within a 5 minute walk
The local area is populated by restaurants
The 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 station
The property was located in a great neighborhood with many excellent cafes and restaurants
Uber ride to downtown attractions
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4. A modern and cosy three-bedroom condo

Enjoy the comfort of this cozy and thoughtful place, with self-check-in, 24-hour text support and amazing neighborhood with great attractions and services at your disposal. Located near the Millenium Park, Sonder offers a great Vrbo experience and can make you feel right at home the moment you step in. This home combines the beauty of bright, living spaces and homely decor with essential amenities such as an ensuite washer & dryer facility, a fully equipped kitchen to prepare your own meals, condo complex facilities such as a fitness room, rooftop and grilling area, and a laptop-friendly workspace including high-speed internet. The location is excellent as well, in close proximity of very popular bars and restaurants if you wish to eat out, shopping centers and attractions like the famous Chicago architecture boat tours and Chicago Riverwalk to take a stroll through.

Sonder | The Plymouth | Modern 3BR + Gym
5 reviews
Apartment 6 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
Please let the local manager know that Courtney was extremely helpful professional polite and friendly
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Welcome to the home of theatre in Chicago

There is a lot to be said about Chicago’s Theatre District. Dine in Michelin Star restaurants and experience what luxury on a plate feels like, or visit museums and step into the past, or be mesmerized by the nightlife here as you sample the best cocktails and dance clubs this city has to offer. But the one attraction you cannot miss here is the variety of shows you can enjoy at over 200 theatres in the area. With Chicago, the sky is the limit! 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. So start booking your vacation now!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Being a military kid, Shamika has lived and travelled all over India, and her nomadic childhood has fueled an immense hunger and fascination for new cultures and languages (she's a polyglot!)...Read more

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