Although it can't claim the title of "The City That Never Sleeps," when the sun goes down Chicago comes even more alive. From night games to art walks, you'll find fun and frolic in what Carl Sandburg called "The City of Big Shoulders." Have a bite, take in some music or simply enjoy the view of the lights and the lake.
Get the Pole Position
If you have an urge to get some evening exercise but find standard workouts boring, check out the beginner's or intermediate pole dancing class at Flirty Girl Fitness. Visit the website for updated class times, but classes are generally offered as late as 8:30 p.m. The gym has 15 poles so you'll be sure to get a chance to get in the swing of things. Swing is also the thing at i.d. gym's Fly Yoga. In this class you'll learn Cirque de Soleil moves on silk hammocks along with yoga, dance and acrobatic routines, all while suspended in the air. You'll never look at fitness the same way again. At the time of publication, Fly Yoga classes are offered on Mondays at 5:45 p.m. and Wednesdays at 6 p.m.
Take It to the Bridge
Leave it to avant-garde architect Frank Gehry to create a silvery serpentine bridge that winds its way across Columbus Avenue to connect Millennium Park with Daley Bicentennial Plaza. The 935-foot span has no railings, just waist-high walls, and the underpinnings of the bridge are hidden by stainless steel shingles, giving the appearance of a giant snake sculpture. A moonlight walk or jog across the 935-foot pedestrian bridge allows for stunning views of Lake Michigan and the nighttime Chicago skyline. Unfettered by railings -- only waist-high walls -- the bridge has a hardwood deck that is much easier on the feet than traditional concrete. Be sure to take time to stop at the viewing platform at the apex of the sinuous architectural marvel.
A Walk in the Park
Make your own walking tour of the city lights by starting at the Park Grill -- open until 9:30 p.m. weekdays and 10:30 p.m. on weekends -- at the Michigan Avenue entrance to Millennium Park. Fortify yourself with a grass-fed beef burger or a roasted beet salad and then head straight for the gigantic shining Anish Kapoor sculpture titled "Cloud Gate," but affectionately known as The Bean. Keep going north to the Great Lawn and the modernistic Jay Pritzker Pavillion. Finally, take the southeastern path for the half-mile walk to the famous Crown Fountain and its LED-lit towers featuring enormous projections of faces that appear to have water spouting from their mouths. When you complete the loop, you'll be almost back to where you started, so it will be easy to find where you parked.
Feel the Rush
For dancing, food and entertainment, there's no better pub crawl than Rush and Division Streets in the otherwise ritzy Gold Coast neighborhood. Dance the night away on two floors of The Hangge-Uppe, bowl a couple of frames at The Lodge or challenge your friends to a game of shuffleboard at Mahoney's Pub. Outgoing types are invited to dance on the bar top at She-nannigans and you can play a rousing game of ping pong at Streeter's, followed by a real Chicago-style dog sent in from the hot dog joint next door.