River North

Main nightlife and dining area with everything from high-end restaurants to speakeasies and clubs. Heavy security presence, but weekend nights get crowded and loud. Good if you want upscale entertainment.

River North is just north of the river - packed with restaurants, bars, nightclubs, and art galleries in a small walkable area. Business district during the day, party zone at night. Hubbard Street has the most nightlife - upscale speakeasies like Three Dots and a Dash, multi-level dance clubs. Mix of tourists, business travelers, and young professionals. Calmer during the day when people visit galleries or brunch. Lots of police and private security around, though weekend nights get loud and crowded with the bar scene. Eating alone is easy - restaurants have bar seating and are used to solo diners, especially at lunch. The Riverwalk is close for daytime walks. More polished and expensive than Wicker Park but less touristy than the Loop. About 5-10 minutes' walk to downtown.