Photo by trenton.badillo

Old Town Chicago holiday rentals

We found 516 holiday rentals — enter your dates for availability

Discover a selection of 13 homes, 18 apartments and other holiday rentals in Old Town Chicago that are perfect for your trip. Holiday rentals provide the best amenities for your family, friends or furry companion, such as a hot tub and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Old Town Chicago

Showing deals for:23 Jan - 30 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 AU$4,658
for 7 nights, 1 apartment
AU$665 per night
includes taxes & fees
Luxury 2BR on Michigan Ave with Private Balcony

Find spaces that suit your style

  • 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

What is the most popular type of holiday home accommodation in Old Town Chicago?
According to our research, houses are considered the most popular type of property in Old Town Chicago. But as you might expect, everyone's idea of an awesome stay differs. Stayz has holiday homes in a variety of shapes and sizes, so you're sure to find the best fit for your needs.
How much does it cost to rent a holiday home in Old Town Chicago?
Property type, length of stay and time of year are among the factors that can determine the price of a holiday home. Simply click on your dates of travel to find your dream escape. From cosy country cottages to sprawling luxury villas, all Stayz holiday homes offer incredible value.
How much does it cost to rent a beach house in Old Town Chicago?
The average price for a holiday home close to the beach in Old Town Chicago will depend on when you'll be there and the style and size of property you're looking for. You can find prices easily and quickly on Stayz by entering the dates you'll be travelling. Then use our filters to pick the number of bedrooms and amenities important to you, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Old Town Chicago?
Yes. There are. You can choose from 25 stays that welcome pets in Old Town Chicago on Stayz. Our furry kids also deserve a getaway, so simply use our search function for pet-friendly holiday homes to book a place where Rover can join in the fun.
What are popular home amenities in Old Town Chicago?
When it comes to home amenities that guests prefer in Old Town Chicago, a fireplace, nearby museums and a firepit rank the highest. With Stayz holiday homes, you'll discover options to fit your style and taste, whether you're travelling with relatives, friends or even pets.
Are there large group holiday homes in Old Town Chicago?
Old Town Chicago has 10 holiday homes that can host 10 or more guests. These properties come with the space and privacy you need to share good times with loved ones.
Are there holiday homes in Old Town Chicago that welcome kids?
Bring the entire family together for an adventure in Old Town Chicago at one of our 25 family-friendly holiday properties. A lot of these stays provide conveniences that are ideal for trips with the kids, including full kitchens, living rooms and entertainment units. Just click on the "Properties good for families" filter and decide on your favourite.
What are the top attractions for families in Old Town Chicago?
There's a ton of amazing things to do and see with the family in Old Town Chicago, including:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Old Town Chicago?
Yes, you'll find five one-bedroom properties in Old Town Chicago to pick from. A one-bedroom holiday home is a superb choice if it's just you and your sweetheart or if you're holidaying alone. Toss in more space, privacy and convenience compared to a regular hotel, and you've got yourself a getaway to remember.
Can I find two-bedroom holiday homes in Old Town Chicago?
You can pick from six two-bedroom holiday homes in Old Town Chicago. Give your little ones the second room or maybe fill it with a couple of your best friends. There's enough space for whoever's fortunate enough to come along for the ride.
Are there holiday homes with WiFi in Old Town Chicago?
Whether you want to keep up with world events, look over emails or post a pic to social media, there are 16 holiday homes with WiFi in Old Town Chicago. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.
How can I find holiday homes with air conditioning in Old Town Chicago?
Decide on your travel dates and then use our filters to search for holiday homes with ac in Old Town Chicago on Stayz. With 23 air-conditioned properties available here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Old Town Chicago?
The minimum required age is typically 16, 18 or 21. It can change across properties on Stayz, so check the rules of your preferred Old Town Chicago stay before booking your escape.
How long can I rent a holiday home in Old Town Chicago for?
The amount of time you can rent an Old Town Chicago holiday home for depends on each property. Simply tap in your travel dates to see available options offering extended stays. They feature all you require to make your extended trip more comfortable and convenient, like air conditioning and kitchens. Some holiday homes might also offer weekly or monthly discounted prices, so you can hang around longer for less.

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