Hotels with pools in Chicago

Hotels in Chicago, Illinois with a swimming pool confirmed in our source data. Indoor or outdoor is not specified in the export.

Pool confirmed
49 qualifying stays

Every property here has a pool confirmed in our source data. What the export does not record is whether it is indoor, outdoor, heated or seasonal - which matters a lot in Chicago.

Chicago's hotel map follows the lake and the Loop. The Loop and River North put you inside the architecture, walking distance from the river and Millennium Park; Lincoln Park and Wicker Park sit further out and quieter. Winter changes the calculation - indoor connections and a bar you would actually use matter more here than in most cities.

What qualifies for this list

Swimming-pool flag set in the source data
Indoor/outdoor, heating and seasonality not specified

49 qualifying stays reviewed. 5 made this shortlist.

We start from every hotel, inn, resort, lodge and bed & breakfast in our United States dataset that scores 8.5 or higher on Booking.com with at least 100 guest reviews. For this page we then looked only at properties in Chicago. See how we select hotels.

The shortlist

Ranked by Charming Score, independent properties first. Every figure below comes from our Booking.com data export (August 2026).

8.8 Charming Score Level Chicago - Old Town, Chicago, IL

Level Chicago - Old Town

Chicago, IL

8.9 guest rating from 426 Booking.com reviews

Hotel
Independent
Pool
Spa & wellness
Terrace

Why it made the listA 8.9 guest rating across 426 reviews is among the strongest Chicago returns in our source data. Booking.com lists it as an independent hotel with a pool, spa and wellness facilities and a terrace. It sits at the top of the collection on price.

Best for: Travelers with pets

Know before you book: No on-site restaurant is listed and pets are allowed, but confirm fees and room limits with the property.

Indicative rate from $294 per night

Check availability

8.6 Charming Score The Robey, Chicago, a Member of Design Hotels, Wicker Park, IL

The Robey, Chicago, a Member of Design Hotels

Wicker Park, IL

8.5 guest rating from 315 Booking.com reviews

Hotel
Independent
4-star
Pool
Spa & wellness

Why it made the listIt ranks #2 of the 49 qualifying Chicago properties we scored. Booking.com lists it as an independent hotel, rated 4 stars with a pool, spa and wellness facilities and an on-site restaurant.

Best for: Slow, restorative stays - City breaks with dinner on site

Know before you book: Our source data does not say whether the pool is indoor or outdoor.

Indicative rate from $194 per night

Check availability

8.5 Charming Score Level Chicago - River North, River North, IL

Level Chicago - River North

River North, IL

8.9 guest rating from 237 Booking.com reviews

Hotel
Independent
Pool
Spa & wellness
Pet friendly

Why it made the listIt ranks #3 of the 49 qualifying Chicago properties we scored. Booking.com lists it as an independent hotel with a pool and spa and wellness facilities. It sits at the top of the collection on price.

Best for: Travelers with pets

Know before you book: No on-site restaurant is listed and pets are allowed, but confirm fees and room limits with the property.

Indicative rate from $315 per night

Check availability

8.1 Charming Score Hilton Grand Vacations Club Chicago Magnificent Mile, Streeterville, IL

Hilton Grand Vacations Club Chicago Magnificent Mile

Streeterville, IL

8.8 guest rating from 121 Booking.com reviews

Hotel
Pool
Spa & wellness
Restaurant
Terrace

Why it made the list121 reviews average out at 8.8 - high enough to clear our Chicago cut-off comfortably. Booking.com lists it as a hotel, rated 3 stars with a pool, spa and wellness facilities and an on-site restaurant.

Best for: Well-rated, no-surprises stays

Know before you book: Our source data does not say whether the pool is indoor or outdoor.

Indicative rate from $202 per night

Check availability

8.1 Charming Score Kasa River North Chicago, Chicago, IL

Kasa River North Chicago

Chicago, IL

8.8 guest rating from 107 Booking.com reviews

Hotel
4-star
Pool
Spa & wellness
Terrace

Why it made the listGuests score it 8.8 over 107 reviews, which is what put it on the Chicago shortlist. Booking.com lists it as a hotel, rated 4 stars with a pool, spa and wellness facilities and a terrace.

Best for: Travelers with pets - Slow, restorative stays

Know before you book: No on-site restaurant is listed and pets are allowed, but confirm fees and room limits with the property.

Indicative rate from $210 per night

Check availability

Availability and rates are checked on Booking.com. If you book through a link on this page we may earn a commission, at no extra cost to you. It never changes which hotels we select or how they are ranked. Full disclosure.

Keep exploring

Hotels in ChicagoAll selected stays Boutique hotels in ChicagoIndependent, small-scale stays Romantic hotels in ChicagoCouples-oriented selections Unique hotels in ChicagoProperties that are not standard hotels Pet friendly hotels in ChicagoPets allowed per Booking.com In-room hot tubs in ChicagoWellness data, verification pending

Common questions

How many hotels in Chicago made this shortlist?

5 properties cleared our criteria and 5 are shown above, ranked by Charming Score. The highest-scoring is Level Chicago - Old Town at 8.8, with a 8.9 guest rating from 426 Booking.com reviews.

What do these stays cost?

Indicative nightly rates for the shortlist run from about $194 to $315 in our data export. Rates move with date, season and availability, so the figure on each card is a starting point rather than a quote.

What is the Charming Score?

It is our own 0-10 selection score, not a guest rating. It combines the Booking.com guest score (45%), review volume (20%), property class (10%), amenity fit (10%), independence and property character (10%) and price positioning (5%). The full method is published on the Charming Score page.

Have you stayed at these hotels?

No, and we do not pretend otherwise. Our selections come from guest data, property facts and location, not from first-hand visits. Our editorial policy explains exactly what we do and do not claim.