Theatre District holiday lettings

We found 674 holiday rentals — enter your dates for availability

Discover a selection of 62 apartments and other holiday rentals in Theatre District that are perfect for your trip. 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:16 Jan - 23 Jan

Image gallery for Luxury 2BR on Michigan Ave with Private Balcony

Living area
9.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Luxury 2BR on Michigan Ave with Private Balcony

Chicago, IL

7% off
Price is £2,464
for 7 nights, 1 apartment
£352 per night
includes taxes & fees
Luxury 2BR on Michigan Ave with Private Balcony

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Frequently asked questions

What is the most popular type of holiday rental in Theatre District?
In the Theatre District of Illinois, apartments are quite popular, with several available for visitors seeking a vibrant experience close to the city's cultural heart. These apartments typically feature modern amenities, including fully equipped kitchens, comfortable living areas, and often access to communal facilities such as gyms or rooftop terraces with city views.
How much does it cost to rent a holiday home in Theatre District?
Prices for holiday rentals in Theatre District vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Theatre District to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Theatre District holiday house rentals?
You can find great discounts on house rentals in Theatre District on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Theatre District?
In the Theatre District of Illinois, holiday rentals commonly feature a variety of popular amenities that enhance the overall guest experience. Many properties include fully equipped kitchens, allowing travellers to prepare their own meals while enjoying the convenience of home. Fitness facilities are also a common offering, suiting those who wish to maintain their workout routines during their stay.
Are there any family house rentals in Theatre District?
In the Theatre District of Illinois, there are several family-friendly house rentals available, making it a great location for families looking to enjoy a blend of culture and entertainment. Properties in this vibrant area often feature spacious living rooms, well-equipped kitchens, and multiple bedrooms, ensuring comfort for larger groups. Many homes also include amenities like Wi-Fi, laundry facilities, and outdoor spaces for relaxation.
Can I rent a holiday home with a pool or hot tub in Theatre District?
In the Theatre District of Illinois, there are several holiday homes available for rent that come with pools and hot tubs. This vibrant area, renowned for its cultural attractions and lively atmosphere, offers a variety of accommodations suitable for travellers seeking relaxation and entertainment. Many of these rentals feature private pools, hot tubs, and expansive outdoor spaces, superb for unwinding after a day of exploring the local theatres and restaurants. Additionally, you can expect amenities like fully equipped kitchens, spacious living areas, and modern conveniences to enhance your stay.
Are there any Theatre District holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Theatre District with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there pet-friendly holiday rentals in Theatre District?
In the Theatre District of Illinois, there are several pet-friendly holiday rentals available, making it a great choice for travellers with furry companions. Many properties in this vibrant area come with modern amenities such as fully equipped kitchens, spacious living rooms, and convenient access to entertainment options. You can expect some rentals to feature outdoor spaces, ideal for relaxing with your pet after a day of exploring the nearby attractions.
Can I find long-stay holiday rentals in Theatre District?
A long-stay holiday rental in Theatre District is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Theatre District for a holiday rental?
The peak season for visiting the Theatre District in Illinois is from May to July, with July being the most popular month. This vibrant period draws in theatre enthusiasts and holidaymakers alike, eager to immerse themselves in the lively atmosphere and attend a variety of performances at renowned venues. The warm weather during these months makes it great for outdoor dining and exploring the nearby attractions.

As temperatures typically hover around the mid-20s Celsius in July, visitors can comfortably enjoy strolls through the district, taking in the sights and sounds of this bustling area. With a number of restaurants, shops, and cultural experiences within walking distance, you'll find plenty to keep you entertained, whether you're indulging in a pre-show meal or discovering local art installations.

If you're looking for a more budget-friendly experience, consider planning your visit in December. While this month is part of the low season, it offers a unique charm with festive decorations and less crowded streets. You can enjoy the holiday spirit, explore the theatres at a more leisurely pace, and find attractive deals on holiday rentals.
Are there any remote work holiday rentals in Theatre District?
In the Theatre District of Illinois, there are several remote work holiday rentals available that cater to the needs of professionals seeking a comfortable work environment. Many of these properties are well-equipped with essential amenities such as reliable Wi-Fi, dedicated desks, and office spaces, allowing for a productive stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Theatre District holiday rental?
Book your Theatre District holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Theatre District?
In the Theatre District of Illinois, particularly in Chicago, visitors can engage in a vibrant cultural scene. The area boasts renowned venues such as the Chicago Theatre and the Goodman Theatre, where acclaimed performances and musicals frequently take place. Holiday rentals nearby often provide easy access to these theatres, as well as a variety of dining options ranging from casual eateries to upscale restaurants.
Can I change or cancel my Theatre District home rental booking on Vrbo?
To find Theatre District holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Theatre District holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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