Theatre District holiday homes

We found 744 holiday rentals — enter your dates for availability

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Dates

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Flexible dates

May 2025

June 2025

Select from 50 houses, 50 apartments and other holiday rentals to find the perfect place for your stay in Theatre District. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for spending time at your holiday home, such as Wi-Fi and cable TV. At the end of the day, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Theatre District

Showing deals for:15 Aug - 22 Aug

Exceptional

(24 reviews)

Chic 2BR 2BA Condo with Balcony - River North Chicago

Chicago, Illinois

8% off

NZ$1,270 per night

includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(226 reviews)

Spectacular Corner 2BR Penthouse in the Loop | Roof Deck

Chicago, Illinois

7% off

NZ$961 per night

includes taxes & fees

Go from traveling to relaxing in minutes with our easy check-in process

Exceptional

(127 reviews)

Kasa | Modern Studio + Steps to the South Loop | Chicago

Chicago, Illinois

8% off

NZ$526 per night

includes taxes & fees

Wake up to nice natural light though the large windows

Exceptional

(14 reviews)

Kasa | Family Friendly 3 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$1,492 per night

includes taxes & fees

Exceptional

(20 reviews)

Kasa | Family Friendly 3 BD + Laptop Friendly | Chicago

Chicago, Illinois

8% off

NZ$1,492 per night

includes taxes & fees

Our apartments have a 4.87 rating across all booking channels for 180,000+ nights hosted, and counting

Exceptional

(9 reviews)

Kasa | Inviting 1 BD + Game Room Access | Chicago

Chicago, Illinois

8% off

NZ$765 per night

includes taxes & fees

Your Kasa experience begins before arrival: we send check-in instructions via email

Exceptional

(12 reviews)

Kasa | Relaxing 1 BD + Near Local Eateries | Chicago

Chicago, Illinois

8% off

NZ$571 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Theatre District

Chicago Theatre

Find the best place to stay - Theatre District

Showing deals for: 13 Aug - 16 Aug

Sonder Jewelers Row

Sleeps 2 · 1 bedroom

for 3 nights, 1 room

NZ$349 per night

includes taxes & fees

Rare Gem! Indoor Pool, Rooftop Deck, Close to Magnificent Mile

Sleeps 2 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

NZ$467 per night

includes taxes & fees

Stay in the Heart of the City! Complimentary Bicycles for exploring!

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

NZ$692 per night

includes taxes & fees

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Theatre District?

A number of things influence how much you pay for a holiday home in Theatre District, like the type of property, season and length of stay. However, all our holiday homes have something in common — unbeatable value. Just add your travel dates to find your home away from home.

How much does it cost to rent a beach house in Theatre District?

When you travel and the size and style of the property will influence how much you’ll pay for your beachside holiday home. Put in your Theatre District travel dates to view your available options on Bookabach. Can’t live without a hot tub? Use the filters to pick the features and amenities you want.

What are the top attractions for families in Theatre District?

Keep the kids occupied at these top family-friendly attractions in Theatre District:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

How old do you have to be to rent a holiday home in Theatre District?

Age restrictions can differ between properties on Bookabach, so be sure to look at the rules of the holiday home in Theatre District you’re interested in. But in general, it’s 16, 18 or 21.

How long can I rent a holiday home in Theatre District for?

It’s up to theatre District property. To see a list of options offering extended stays, just type your travel dates and number of people into the Bookabach search page. You can enjoy having the place to yourself, along with amenities such as a kitchen, air conditioning and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.