Chicago Hotels with Rooftop Pools

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago this weekend is JPY 68,324 per night. For a 4-star hotel, the average cost is JPY 85,606 per night. If you're looking for a luxury experience, 5-star hotels in Chicago this weekend typically cost JPY 191,531 per night.

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Chicago during weekdays is JPY 57,529 per night. For a 4-star hotel, you can expect to pay around JPY 77,189 per night. If you're seeking a luxury stay, 5-star hotels in Chicago generally cost JPY 176,044 per night on weekdays.

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.

Some of the top hotels in Chicago near Millennium Park include The Palmer House Hilton (from JPY 35,586), Hyatt Regency Chicago (from JPY 45,098) and Swissotel Chicago (from JPY 30,073), all offering easy access to Millennium Park, making them ideal for visitors looking to explore the area.

Feel tired from travelling? Hilton Chicago O'Hare Airport (from JPY 33,291), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from JPY 24,891) and Chicago Marriott Downtown Magnificent Mile (from JPY 41,691) provide highly rated spa services.

Best Western River North Hotel (from JPY 24,773), Hilton Garden Inn Chicago Downtown/Magnificent Mile (from JPY 24,891) and Embassy Suites by Hilton Chicago Downtown River North (from JPY 30,310) are hotels with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

Swissotel Chicago (from JPY 30,073),JW Marriott Chicago (from JPY 41,620) and Trump International Hotel & Tower® Chicago (from JPY 80,093) provide high-quality breakfast. Start your day with a delicious breakfast!

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.