Chicago hotels with a pool
Compare Chicago hotels across hundreds of providers, all in one place
Find hotels in Chicago with spas, rooftop pools and more
Look out for last-minute deals for Chicago hotels with a pool
Tried and trusted Chicago hotel providers
See all Chicago hotels with a pool
Other travellers love these Chicago hotels with a swimming pool
The best hotels in Chicago with a pool, according to others. These spots were rated well for cleanliness, customer service and location.
Fast facts
Sleep easy, armed with the stuff that's good to know before you go.| Rated best by travellers | The Robey, Chicago, a Member of Design Hotels |
|---|---|
| Cheapest hotel found | $282, The Penthouse at Grand Plaza |
| Cheapest month to stay in Chicago | February |
| Most expensive month | July |
Choosing a Chicago hotel with a pool
Get the best rate
Use our calendar view to find the cheapest month or even day of the month to stay in a Chicago hotel with a pool.
Find your fit
From family hotels with several pools to luxury pads with private pools, compare Chicago hotels to find something that suits.
Stop by the spa
Plenty of hotels with pools have spas, so you can indulge in some post-dip pampering. Book a massage, or unwind in the sauna or steam room.
Stay flexible
Some hotels offer flexible booking options, such as free cancellation up to a day before your stay. Ideal for securing your hotel if you’re not certain on dates.
Relax on the roof
Want to elevate your travel memories? Look out for a hotel with a rooftop pool and enjoy skyline views while you swim. You’ll only find these in certain cities.
Find a cheap deal
With affordable hotels and last-minute prices, you can book a Chicago hotel with a pool that won't break the bank.
