Chicago Hotels with a Pool

With Hotels.com, you can book a hotel with a pool in Chicago for as low as $25 per night.

A quiet, serene pool is a fantastic way to get away from the daily stresses of life and finally relax on your trip. Heading down to the pool can be also be a refreshing way to get some exercise on your trip besides hitting the hotel gym. Stay warm any time of year at an indoor pool, or soak up the sun at our hotels featuring outdoor pools.

If you're traveling with kids in Chicago, the pool can be a handy way to keep them active and entertained. Lounge around and stay dry, or get out and go swimming with the whole family.

Can't decide which accommodation works best for you? We recommend you explore the complete selection of hotels in Chicago by further narrowing down the list by star ratings, price, or using the map to find how hotels near top attractions. Be sure to check each property for any specific amenities you may enjoy during your stay, such as a hot tub, infinity pool, or poolside bar.

Here's a quick overview of what our verified guests have rated as the best free breakfast hotels for:

• Cleanliness: The Penthouse at Grand Plaza
• Service: The Penthouse at Grand Plaza
• Comfort: The Penthouse at Grand Plaza
• Condition: Loews Chicago Hotel

Rest assured, no matter where you’re traveling, Hotels.com has a great deal for you. So pack a swimsuit and have a great trip!