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Top Romantic South Side Hotels

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

11 min drive from University of Chicago

Ready for a romantic getaway? You are sure to enjoy the garden, lobby fireplace, and premium mattresses at this boutique hotel. You'll also appreciate the luxury ...

Chinatown Hotel Chicago

214 West 22nd Place Chicago IL

11 min drive from University of Chicago

Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...

5.6/10 (1,000 reviews)

This was hands down the worst hotel I've ever seen. Mattress was covered in piss stains, there was puke on the computer desk, the blinds were broken, dresser was missing drawers, the bad frame was straight up made of 2x4's, and the dude at the front desk was on a personal call the entire time he ...

Reviewed on Mar 23, 2026

See all 463 properties in South Side

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.