Chicago rentals with pool

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.

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.

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.

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.