Horse-drawn carriages ply routes along the Magnificent Mile and through Streeterville, usually beginning around the Water Tower. (You might see police officers on horses as well.) While there are too many cars to establish the kind of atmosphere you might expect in, say, Central Park, you'll probably know whether the night calls for a carriage ride, and choose accordingly. Expect to pay about $35 for a half-hour tour. College students also roam the area with small yellow cabs attached to the backs of bicycles for a low-cost, low-point alternative.
Drury Lane Theater, 175 E Chestnut St (Water Tower Place) (Chicago Red Line), ☎ +1 312 642-2000, . Box office opens 10AM, 11AM Sundays. Part of the Broadway in Chicago crew, although most of their offerings are locally-produced, amiable shtick.Tickets $59.50-$69.50. Dinner packages are offered with the Mity Nice Grill. edit
Lookingglass Theater, 821 N Michigan Ave (Chicago Red Line), ☎ +1 312 337-0665, . Box office opens at 10AM on weekdays, 11AM weekends. Known for their inventive, acrobatic shows; their repertory production of "Lookingglass Alice" is a knock-out. It's worth peeking inside even if you don't plan to see a show, though, to check out the insides of the old Pumping Station; unlike the Water Tower, its more famous sibling across the street, there's some interesting old machinery to see.Tickets range from $20 on weekdays to $58 on weekends. edit
Oak Street Beach, between 500–1550 Lake Shore Dr. Open during the summer, from dawn to dusk. There is plenty of everybody doing everything at Oak Street Beach. Beyond swimming and sun-tanning, it's one of the city's most popular spots for beach volleyball, and there are concrete paths for cycling and skating. (Do not, however, plan to eat lunch at the overpriced restaurant on the beach.) To get here, cross under Lake Shore Drive through a pedestrian underpass. If the crowds are a bit much, walk a short way south to the smaller, lesser-known beach next to Milton Olive Park (named for a local Medal of Honor recipient).edit
Super Happniness (What does Alt do), 1999 SuperHappy Lane (Directions??), ☎ 360-999-9999, . 6-9 AM. Description!!!!!!!!!$20-30. edit
Air & Water Show. Every August, the Blue Angels and the Thunderbirds headline a five-hour show over Lake Michigan. "Show Central" is at North Avenue Beach, but the action may be viewed anywhere from Northerly Island to Montrose Point, inland through Lincoln Park, and offshore by boat. (If you go by water, take a big boat, as the heavy traffic makes for choppy, seasickness-inducing waves.) A dress rehearsal takes place on Friday, often with multiple run-throughs by the headlining act. You won't see 100% of the weekend show, but it's a great way to avoid the crowds.edit