Top Chicago rentals with pool or private pool - Illinois

Explore Chicago rentals with pools

Level Chicago – Old Town

Sleeps 8

Your Home Away From Home! Outdoor Pool, Pets Allowed, Near Lindholm Park!

Sleeps 3 · 1 bedroom · 1 bathroom

Top rated rentals with pools - Chicago

Premier Host

Excellent location.

Fantastic property with amazing views. Ideally located for everything that Chicago has to offer.

Steven W.

Stayed May 2025

Find spaces that suit your style

House

Condo/Apartment

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, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Chicago?

Take your pick of 496 holiday rentals with a pool in Chicago that offer all the privacy, space and amenities you need for a splashing great time. Check out houses in some of the most popular areas such as Theatre District, The Loop and Central Chicago.

How much does it cost to stay in a holiday rental with a pool in Chicago?

If you're hoping to save on your holiday rental with a pool, Vrbo's filters can help. After your initial search, tailor your results according to your preferences, including location, price and features and amenities. We've got accommodation in Chicago for all types of budgets and needs, so make the most of our filters to discover your dream stay.

When is the best time to book a holiday rental with a pool in Chicago?

If you'd love to visit Chicago at a busy time, consider going in May. That's when temperatures range from around 10 ºC (10ºC) to 16 ºC (16ºC), and when many guests stay in a holiday rental with a pool in this destination. Of course, there are other excellent times to travel to this corner of Great Lakes, so do some research into which season or month works best with your plans.

What holiday rentals with a pool in Chicago have nice views?

Vrbo has a range of excellent holiday rentals with a pool in Chicago, including houses with urban views. When you aren't touring the sights, relax by taking a dip and gaze at scenes that are their own attraction.