Chicago

Chicago Hotels with Rooftop Pools

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Hotel Star Rating
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Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

We found 8 Chicago hotels with Rooftop Pools for you

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Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotel near River North,Chicago
"The Best Western River North Hotel is a practical choice for exploring Chicago, thanks to its excellent location near the Magnificent Mile. The rooms are clean and functional, providing a comfortable base for a short stay. One of the highlights is the rooftop deck, which offers great views of the city skyline. Having an indoor pool and on-site parking is also a major convenience for this downtown area. It offers reliable value for those who want to be close to the action without the luxury hotel price tag. And we had an amazing walk to union train station"
Good
57 reviews
7.9/10
1 night
From €105
Check Availability
99+
Hotel near West Loop,Chicago
"During the epidemic, breakfast was filled with bread, fruit and coffee in kraft paper bags, but check in and check out were quite fast. The parking lot is very small. It is not easy to see $50 a night at night. The overall environment of the hotel is very good, the facilities are very new, the decoration is also very good, there is a swimming pool and a gym, the price is good, it is recommended!"
Very Good
104 reviews
8.9/10
1 night
From €262
Check Availability
99+
Hotel near Streeterville,Chicago
"great safe location , the rooftop pool with skyline views and grab and go with food and drinks was awesome."
Very Good
283 reviews
8.8/10
1 night
From €166
Check Availability
78
Hotel near Streeterville,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Great
101 reviews
9.0/10
1 night
From €248
Check Availability
96
Hotel near West Loop,Chicago
Featured facilities: Swimming Pool, Bar, Fitness Room
Great
101 reviews
9.0/10
Check Availability
99+
Hotels in Chicago
Featured facilities: Swimming Pool, Fitness Room, Laundry Service (On-Site)
Very Good
41 reviews
8.9/10
1 night
From €110
Check Availability
99+
Hotel near River North,Chicago
"The front desk service is very good But the efficiency of valet parking needs to be improved. It took about 20 minutes for the bus to arrive. The rooftop bar is not open in winter. Looking forward to staying again in the future."
Great
108 reviews
9.0/10
Check Availability
99+
Hotel near Wicker Park,Chicago
Featured facilities: Swimming Pool, Bar, Massage Room
Great
101 reviews
9.1/10
1 night
From €201
Check Availability
See All Hotels with Rooftop Pools in Chicago

Frequently Asked Questions

What is the average price of a hotel in Chicago this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago this weekend is €250 per night. For a 4-star hotel, the average cost is €336 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost €902 per night.

What are the best places to stay in Chicago?

Some of the best places to stay in Chicago are near popular attractions like Millennium Park, Willis Tower and Magnificent Mile, offering easy access to key sights and amenities.

What are the top hotels in Chicago near Millennium Park?

Some of the top hotels in Chicago near Millennium Park include The Palmer House Hilton (from €152), Swissotel Chicago (from €175) and L7 Chicago (from €131), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

Which hotels in Chicago are worth visiting for their spa experience?

Which hotels in Chicago provide airport transfer services?

Which hotels in Chicago have swimming pools?

What hotels in Chicago offer an especially good breakfast ?

Warwick Allerton Chicago (from €81),Hilton Chicago O'Hare Airport (from €172) and Swissotel Chicago (from €175) provide high-quality breakfast. Start your day with a delicious breakfast!

How to get good deals on hotels in Chicago?

To get the best hotel deals, try these Trip.com tips: 1. Log In Trip.com first and unlock member-only rates and Trip Coins (loyalty points). 2. Book Midweek: Sun–Thurs stays are much cheaper than weekends. 3. Set Price Alerts: Monitor price drops and rebook if needed. 4. Use “We Price Match” Policy: If you find a lower price elsewhere, Trip.com will refund the difference. 5. Avoid major holidays, conventions, and big events. 6. Check the Deals Page to see what promotions are available now on Trip.com.