
By: Greg Mattson, Founder & Editor, Excellent Romantic Vacations.com. We personally visit and review hotels independently, at our own expense.
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.
Check Out a Romantic Private Pool Suite Near ChicagoThese 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:
Swimming Pool Suite, Champagne Lodge, Willowbrook IL
Romantic Pool Suite, Sybaris Frankfort IL
Plunge Pool Suite, Sybaris in Northbrook, Illinois
Sybaris Pool Suite in Downers Grove, IL
Glenwood Estates, IL Vacation Rental w/Private Pool
Greg Mattson, ERV Editor, brings 35+ years of travel expertise, with over a million miles across 28 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.
Editorial Policy: Excellent Romantic Vacations maintains complete editorial independence. We personally visit and review many hotels independently, at our own expense, to ensure that our feature recommendations reflect genuine travel experiences and honest opinions. When a property has not yet been visited by us, all details are carefully verified using official hotel websites and trusted traveler reviews from sources such as TripAdvisor and Google. Disclaimer: We do our best to keep hotel and suite information accurate, with details verified by ERV using official hotel websites and supported by sources like TripAdvisor and Google user reviews. Each listing shows the date we last confirmed amenities, but hotel features may change. Please verify directly with the hotel before booking.
*ERV Rating: Our unique, non-scientific ratings for romantic accommodations are based on:
Please Note: percentage ratings are for comparative use only and not absolute.
√ERV Clean Score: A cleanliness rating (A = 80–100%, B = 70–79%, C = 60–69%, etc.) based on our own stays and/or recent guest reviews.
Photos: Images on our site come from our own hotel stays, official hotel sources, and TripAdvisor Professional Photos (used with permission). Because hotels may update their décor and room layouts, photos may not always show the exact suite you’ll book. For the most current images, please check directly with the hotel.