Downtown Chicago apartments

Choose from apartment holiday rentals around Downtown Chicago and then get ready for your next big adventure. Wherever you’re headed, our condos and apartments will provide you with all the amenities and comforts of home.

A range of factors will determine the price of an apartment holiday rental in Downtown Chicago, such as the size of the property and how long and when you plan to stay. All you have to do is enter your holiday dates and preferences to find an apartment that meets your taste and budget.

Peak tourist seasons and major events usually bring more people to Downtown Chicago. You may want to avoid these periods if you prefer things a little quieter. But if being caught up in the hustle and bustle sounds like the ideal escape, March is the month to book your holiday condo rental.

The only thing better than a homey apartment holiday rental is one that offers a view. We’ve got stays in Downtown Chicago that feature scenic vistas just beyond your window. Use our filters to narrow your search for properties set in idyllic areas or with specific views. Your next job? Kick back and soak it all in.

Escape for the weekend at one of our holiday apartment rentals in Downtown Chicago. Check the availability by entering your desired travel dates and then gather the family for a few days of adventure and relaxation. If you can’t find the perfect holiday condo rental right away, simply adjust your dates and search again.

Our luxe apartment holiday rentals in Downtown Chicago are all about making sure you’re relaxed and pampered. They combine practical features like kitchens and living spaces with extra perks such as modern appliances, lavish interiors, pools and hot tubs. And the best bit? Vrbo’s holiday condo rentals are completely private so you and your family can have the opulence and unparalleled comfort all for yourselves.

There are plenty of incredible experiences to be had when you book an apartment holiday rental in Downtown Chicago. What you enjoy doing and the people you’re travelling with will help you decide what to see and do, so do a little research before you set off.

With more than 2 million holiday properties to pick from around the world, we help guests find a stay that offers loads more than the typical hotel room experience. Whether that’s an ideally located apartment holiday rental or even a houseboat, you’ll always get the whole place to yourself. And with our free loyalty programme, One Key™, you can earn and use OneKeyCash™* on eligible bookings on Vrbo. What’s more, our Book with Confidence Guarantee and flexible cancellation policies mean you can book with peace of mind. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.