
By: Greg Mattson
Founder & Editor, Excellent Romantic Vacations.com.
Updated: Aug 18, 2025
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Booking accommodation in the greater Chicago area with your own private pool can be a real challenge, so take a close look at this special selection of hotels and rentals with pools in the Windy City.
These hotel and vacation rental units fit a wide variety of getaways, from couples to families and larger groups. They don’t have lengthy minimum stay requirements, so they’re perfect for a weekend getaway or short-term rental. And they all feature a private pool for your own use, not shared with anyone else. Have a great getaway!
(Please Note: Guest use of swimming pools is unsupervised and at your own risk. Pool rules as established by the hotel or owner must be followed at all times. Never leave children unattended near a pool. Availability of pools and other amenities can be seasonal only and change at any time, so please check with the property before making firm travel plans.)
Please Note: Children and Pets are not allowed at the following properties:

Greg Mattson, ERV Editor, brings 35+ years of travel expertise, with over a million miles across 29 countries and 40 U.S. states. A former travel agent & airline professional, he’s stayed in hundreds of hotel honeymoon suites with jetted tubs & walk-in rain showers, curating top romantic getaways for Excellent Romantic Vacations.
Reviews & Ratings: Excellent Romantic Vacations (ERV) provides independent editorial reviews. Our ERV Rating* and ERV √Clean Score are subjective comparative guides based on our proprietary research and guest sentiment. These ratings represent our editorial opinions and are intended for general comparison purposes only.
Verification of Details: While we verify details via official hotel sources and traveler reviews, amenities like Whirlpool or JACUZZI® tubs can change without notice. Guests should confirm specific room features directly with the property at the time of booking. Excellent Romantic Vacations.com cannot guarantee the availability of specific amenities or room features.
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