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[3% CashBack] Best Vrbo Vacation Rentals In Chicago's Theater District, Illinois - Updated 2020

vrbo chicago theater district

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. Grand three-bedroom apartment with stunning views (from USD 525)

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!
50 reviews
Apartment 6 Guests 3 Bedrooms 3 Bathrooms
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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2. Tranquil and beautiful home with lovely decor (from USD 268)

This unit comes with a rooftop deck from where you can enjoy the skyline views around the West Loop. It is centrally located, and at walking distance from the El, Millenium Park, Grant Park, and Magnificent Mile. The home itself reflects decadence and luxury with custom artwork and elegant furnishings that lend a tranquil and classy feel to the home. With three bedrooms, one with a king-sized bed and the other two with queen-sized beds, this home can easily accommodate a family or a group of friends. It also has two full baths, which is a blessing when you’re staying with many people, as well as complimentary toiletries, a laptop-friendly workspace, free WiFi, smart television with DirectTV, and a fully stocked kitchen. All in all, it offers a comfortable stay at home with the luxuries of a hotel.

Domio | Loop | Architectural 3BR Penthouse
16 reviews
Apartment 8 Guests 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
The beds were very comfortable
Although the apartment is advertised as three bedrooms two of the bedrooms do not have doors and are very small
The master sink had a large orange stain around the facets
A few minor other issues included no iron (even though we had the ironing board)
The door on the master bedroom would not close due to broken hinges
A towel bar over the sink was broken and not replaced
The condo was clean and beautiful
The rental was clean and the price was reasonable
It didn't interrupt our sleep but was annoying in the early evening and morning
The doorman was pleasant and helpful
We had a problem with the washer
nice furniture and the security/doorman were all awesome
broken handles broken ice maker
We walked most places and used Uber when needed
The location is just a block from the river
The apartment was very clean and the beds were comfortable Great location - very near to the River Walk and a short walk from the Art Institute and Millennial Park
Location was close to everything we wanted in Chicago: theater district river walk shopping and Millennium Park and the lake
This is a comfortable clean apartment in a fantastic location just one block off of Wacker and the Riverwalk Property manager
We actually got used to the sound of the "L" and enjoyed the sound as part of the experience of the city Highly recommended
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3. Spacious and comfortable one-bedroom unit (from USD 185)

This may be a one-bedroom home, but don’t underestimate how spacious it is! You step into a large living room that offers beautiful views and light-filled living space with high-vaulted windows, then move into a custom-built kitchen with marble countertops, beautiful bathrooms with adjustable showerhead, a soaking tub and marble vanity, this home oozes luxury proving that less is more! Aside from all this, it also includes an indoor pool and party room on the premises, along with a huge fitness facility and free parking is available on request. The host will provide you with fresh linens and towels, and everything you need for a cozy yet decadent stay. So kick back and slip into luxury!

11 reviews
Apartment 3 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The room itself is set up for cooking and eating your own food
Room clean except for some carpet stains in bedroom berber carpet
Great apartment and building Great amenities in building
Blinds shielded from most of street light but some woman on the street was ranting at 2-3 am for about half hour to an hour
360-Chicago in the Hancock building
Jason was very responsive to emails
the washer/dryer made it easy for us to only pack carry-ons and wash clothes during the trip I would definitely stay here again
had a great shower and
Most hotels were sold out so prices were high
the River Walk Navy Pier
The location is within walking distance of many attractions in the loop and safe Older building that has apparently been totally renovated Starbucks and Dunkin Donuts within 1/2 block
Perfect location for exploring DT Chicago
The Clark/Lake transfer station is one block away which made it easy to get to and from the airport as well as the Shedd Aquarium Field Museum and Second City
a little spartan Bright light outside and street noise at night
Enjoyed stay and will remember property for future trips to Chicago
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4. A modern and cosy three-bedroom condo (from USD 118)

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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5. Charming and modern three-bedroom stay with incredible pier views (from USD 578)

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!

FREE TRIP INS | PARKING IN BLDG | 3BR Luxury Corner Sky Loft | Navy Pier Views | Gym & Pool
43 reviews
Apartment 8 Guests 3 Bedrooms 3 Bathrooms
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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6. Stunning and luxurious loft (from USD 915)

A gorgeous loft with incredible views awaits you in the heart of Chicago, with every luxury at your disposal. Step into a huge open-concept loft living room that is perfect for groups or families, and has a large smart television, foosball table, and a bar, and opens into the fully equipped state-of-the-art kitchen with professional grade appliances and quartz countertop islands! The three bedrooms have two queen-sized beds and a king-sized bed, along with thoughtful and attentive details such as a reading nook, ensuite baths in each bedroom, his and her closets in the master bedroom, and a free-standing tub, steam shower, and double vanities. The main highlight of this loft is the neighborhood, which is alive with activity day or night. There are a variety of options to explore, including a dynamic nightlife, urban park spaces, award-winning restaurants, a shopper’s paradise, incredible architectural marvels, and more!

3 BDR Downtown Luxury Loft-Spacious, Safe & Secure
6 reviews
Apartment 8 Guests 3 Bedrooms 3 Bathrooms
Top guest reviews
Great location beautiful property perfect for 3 couples
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7. Beautiful views from this three-bedroom gorgeous accommodation (from USD 633)

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!

FREE TRIP INS | PARKING IN BLDG | Spacious 3b/3b Lux Skyview of Navy Pier Gym & Pool by ENVITAE
18 reviews
Apartment 8 Guests 3 Bedrooms 3 Bathrooms
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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8. Aesthetically pleasing and modern two-bedroom abode

In the midst of the vivid and magical Fulton Market District, you can step into this cozy yet spacious apartment that you get to call your home for the duration of your vacation. With enough space to be able to accommodate five people comfortably, this home is perfect for solo travelers, couples or small families. The owner, Matthew Conti, is bilingual and can speak both Spanish and English, and guests highly compliment how friendly and hospitable he is. While this condo is located in the heart of the Fulton Market District, it is still tranquil and very quiet. However, the lack of an elevator may mean that you might have to arrange for special accommodation in case you or a companion is a senior or differently abled. The location is very close to grocery stores and entertainment options, making it a great place to stay if you wish to stroll through the streets and just take in the culture.

The Annex II Huge 1,600 Sq feet
216 N Jefferson St
6 reviews
Apartment 5 Guests 2 Bedrooms 1 Bathroom

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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!

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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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