Chicago is not known as a beach destination, but Lake Michigan is the largest freshwater lake located entirely within the United States, and Chicagoans flock to its sandy shores. Anyone can show up and swim — there are no admission fees, miles of beaches are within walking distance of the Red Line, and almost none of the lakefront is spoiled by "private" beaches. Despite the latitude, the water is quite warm in the summer and early fall (check with the NOAA for temperatures). The Chicago shore has been called the second cleanest urban waterfront in the world, although bacteria levels in the water do force occasional — but rare — beach closures (which are clearly posted at the beach, and online). Lifeguards will be posted (usually in a rowboat) if the beach is officially open.
Oak Street Beach and North Avenue Beach (in the Near North and Lincoln Park) are the fashionable places to sun-tan and be seen, but Rogers Park has mile after mile of less pretentious sand and surf. Hyde Park's Promontory Point is beautiful, and offers skyline views from its submerged beach by the rocks (although a swim there is technically against city rules). Hollywood Beach in Edgewater is the main gay beach.
Navy Pier was built in 1914 and was served as a naval base during both world wars. It is now Illinois' number one most visited tourist attraction (ahead of some boring exurban megamalls). The pier has carnival rides, including the popular ferris wheel, as well as theater, restaurants, arcades, bars, shops, and most importantly great views back towards the city.
Where there are beaches, there are lakefront parks. During the summer months, the parks are a destination for organized and impromptu volleyball and soccer games, chess matches, and plenty more, with tennis and basketball courts dotted along the way.
In the Loop, Grant Park hosts music festivals throughout the year, and Millennium Park is a fun destination for all ages, especially during the summer.
Lincoln Park stretches for seven miles along the lakefront, with numerous bicycle paths, beaches, harbors and museums. Situated just east of the Lincoln Park neighborhood is the cheerful (and free) Lincoln Park Zoo which welcomes visitors every day of the week, with plentiful highlights like the Regenstein Center for African Apes. There are also terrific parks further away from the lake. In Hyde Park, Midway Park offers skating, and summer and winter gardens in the shadow of the academic giant, the University of Chicago, and Jackson Park has golf, more gardens and the legacy of the city's shining moment, the 1893 World's Colombian Exposition. In Bronzeville, Washington Park is one of the city's best places for community sports. And that's just a brief overview. Almost every neighborhood in Chicago has a beloved park.
If you're absolutely determined and you plan carefully, you may be able to visit Chicago during a festival-less week. It's a challenge, though. Most neighborhoods, parishes, and service groups host their own annual festivals throughout the spring, summer, and fall. There are a few can't-miss city-wide events, though. In the Loop, Grant Park hosts Taste of Chicago in July, and four major music festivals: Blues Fest and Gospel Fest in June, Lollapalooza in August, and Jazz Fest over Labor Day Weekend. All but Lollapalooza are free. The Chicago-based music website Pitchfork Media also hosts their own annual three day festival of rock, rap, and more in the summer at Union Park on the Near West Side.
With entries in every major professional sports league and several universities in the area, Chicago sports fans have a lot to keep them occupied. The Chicago Bears play football at Soldier Field in the Near South from warm September to frigid January. Since the baseball teams split the city in half, nothing seizes the Chicago sports consciousness like a playoff run from the Bears. Aspiring fans will be expected to be able to quote a minimum of two verses of the Super Bowl Shuffle from memory, tear up at the mention of Walter Payton, and provide arguments as to how Butkus, Singletary, and Urlacher represent stages in the evolution of the linebacker, with supporting evidence in the form of grunts, yells, and fists slammed on tables.
The Chicago Bulls play basketball at the United Center on the Near West Side. While quality of play and ticket prices may never again reach Jordan-era mania, they're still an exciting team to watch, led by young star Derrick Rose. The Chicago Blackhawks share quarters with the Bulls. As one of the "Original Six" teams in professional hockey, the Blackhawks have a long history in their sport, and the team is experiencing a renaissance after capturing the Stanley Cup in 2010 for the first time in 49 years. Home games for both teams tend to sell out, but tickets can usually be found if you check around. Both the Bulls and the Blackhawks play from the end of October to the beginning of April.
It's baseball, though, in which the tribal fury of Chicago sports is best expressed. The Chicago Cubs play at Wrigley Field on the North Side, in Lakeview, and the Chicago White Sox play at U.S. Cellular Field (Comiskey Park, underneath the corporate naming rights) on the South Side, in Bridgeport. Both franchises have more than a century's worth of history, and both teams play 81 home games from April to the beginning of October. Everything else is a matter of fiercely held opinion. The two three-game series when the teams play each other are the hottest sports tickets in Chicago during any given year. If someone offers you tickets to a game, pounce.
There are plenty of smaller leagues in the city as well, although some play their games in the suburbs. The Chicago Fire (Major League Soccer) play soccer in the suburb of Bridgeview, near the Southwest Side of Chicago, the Chicago Red Stars (National Women's Soccer League) play at Benedictine University in suburban Lisle, the Chicago Sky play women's professional basketball at the Allstate Arena in the suburb of Rosemont, also home to the Chicago Wolves minor league hockey team, and the Windy City Rollers skate flat-track roller derby in neighboring Cicero. Minor league baseball teams dot the suburbs as well.
While college athletics are not one of Chicago's strong points, Northwestern football (in Evanston) and DePaul basketball (off-campus in Rosemont) show occasional signs of life. If you find yourself in Hyde Park, ask someone how the University of Chicago football team is doing — it's a surefire conversation starter.
Modern American comedy — the good parts, at least — was born when a group of young actors from Hyde Park formed The Compass Players, fusing intelligence and a commitment to character with an improvisational spark. One strand of their topical, hyper-literate comedy led, directly or indirectly, to Shelly Berman, Mike Nichols & Elaine May, Lenny Bruce, M*A*S*H and The Mary Tyler Moore Show; another strand, namely The Second City, led to Saturday Night Live and a pretty huge percentage of the funny movies and television of the last thirty years. Still in Chicago's Old Town (and few other places as well), still smart and still funny, Second City does two-act sketch revues followed by one act of improvisation. If you only see one show while you're in Chicago, Second City is a good choice.
Improvisational comedy as a performance art form is a big part of the Chicago theater scene. At Lakeview and Uptown theaters like The Annoyance Theater, I.O., and The Playground, young actors take classes and perform shows that range from ragged to inspired throughout the week. Some are fueled by the dream of making the cast of SNL or Tina Fey's latest project, and some just enjoy doing good work on-stage, whether or not they're getting paid for it (and most aren't). There's no guarantee that you'll see something great on any given night, but improv tends to be cheaper than anything else in town, and it can definitely be worth the risk. Another popular theater experience is the comedy/drama hybrid Too Much Light Makes The Baby Go Blind, offering 30 plays in 60 minutes every weekend in Andersonville.
Steppenwolf, in Lincoln Park, is Chicago's other landmark theater. Founded in 1976, they have a history of taking risks onstage, and they have the ensemble to back it up, with heavyweights like Joan Allen, John Malkovich, and Gary Sinise. Steppenwolf isn't cheap any more, but they mix good, young actors with their veteran ensemble and still choose interesting, emotionally-charged scripts. It's the best place in town to see modern, cutting-edge theater with a bit of "I went to..." name-drop value for the folks back home.
Most of the prestige theaters, including the Broadway in Chicago outlets, are located in the Loop or the Near North. Tickets are expensive and can be tough to get, but shows destined for Broadway like The Producers often make their debut here. For the cost-conscious, the League of Chicago Theatres operates Hot Tix, which offers short-notice half-price tickets to many Chicago shows.
One theater to see, regardless of the production, is The Auditorium in the Loop. It's a masterpiece of architecture and of performance space. Designed by Dankmar Adler and Louis Sullivan, who were on a commission from syndicate of local business magnates to bring some culture to the heathen city, it was the tallest building in Chicago and one of the tallest in the world at the time of its opening in 1889, and it's still an impressive sight, inside and out.
Chicago has a strong, passionate bicycle culture, and riding opportunities abound. Pedaling your way around the city is one of the best ways to get to know Chicago. And the terrain is mostly flat — a boon for easy-going cyclists! If you don't have a bike, that's no problem. Bobby's Bike Hike is probably best for longer-term rentals, with a central bike rental location near Navy Pier, at the old North Pier at 465 N. McClurg Court. Alternately, the city's new, distinctively blue DIVVY bike sharing system has kiosks throughout the central area, near the lake and the parks. 24 hour passes cost $7, but that doesn't mean you keep the bike for 24 hours — it means you can take an unlimited number of rides, up to 30 minutes each, over the course of those 24 hours, parking at the same or different kiosks along the way. Hence, the system is geared toward short trips, not leisurely tourist rides along the lakefront. DIVVY launched with 750 bikes at 75 stations spanning from the Loop north to Fullerton Ave, west to Damen Ave, and south to 23rd St. The system is planned to grow to 4,000 bicycles at 400 stations by Spring 2014.
The scenic Lakefront Trail runs for 18 continuous miles along the city's beautiful shoreline, from Hollywood Beach in Edgewater to the magnificent South Shore Cultural Center. Even while riding at a moderate pace, traveling downtown along the lakefront can be faster than driving or taking the CTA! If you're starting from downtown, you'll be at the approximate midpoint of the trail. Head south if you want a speed workout with fewer crowds, or north to see more of the locals at play.
Further inland, many streets have bike lanes, and signs direct riders to major bike routes. The City of Chicago maintains helpful bicycle resources online, including major civic bike events and (slow) interactive maps of major streets with bike lanes. Of special note is the unofficially named Hipster Highway which is Milwaukee Avenue from Kinzie St in the West Loop to Logan Square, which is a popular bike route where bicyclists oftentimes outnumber cars! Also of note is Dearborn Street in the Loop which is a two way protected bicycle lane on a one way highway (cycle track for you Europeans) complete with special signals for bikes. Note that if going against car on Dearborn traffic you need to be more cautious about pedestrians who aren't expecting bicycles heading opposite the way they are used to looking.
Bicyclists have to follow the same "rules of the road" as automobiles (stop at red lights and stop signs, etc.). Bicycle riding is not allowed on sidewalks (except for children under age 12). This rule is strictly enforced in higher density neighborhoods, mostly areas near the lake, and is considered a criminal misdemeanor offense. You must walk your bike on the sidewalk.
CTA buses are all equipped with front bike racks, which carry up to two bicycles, and 'L' trains permit two bicycles per car except during rush hour (roughly 7-9:30AM and 3:30-6:30PM weekdays, excluding major holidays on which the CTA is running on a Sunday schedule). With the buses, inspect the rack closely for wear or damage and be absolutely certain that the bike is secured before you go, lest it fall off in traffic (and be immediately flattened by the bus). The CTA will fight tooth and nail to avoid reimbursing you for the loss, and the driver might not stop to let you retrieve it.
Bikes may be rented from the North Avenue Beach House (Lincoln Park), Navy Pier, (Near North), the Millennium Park bike station (Loop), and from several bike shops in the city. Another option is to contact the terrific Working Bikes Cooperative, an all-volunteer group of bike lovers that collects and refurbishes bikes, and then sells a few in Chicago to support their larger project of shipping bikes to Africa and South America. You could buy a cheap bike and donate it back when you're done, or even spend a day or two working as a volunteer.
For an opportunity to connect with the local bike community and take a memorable trip through the city, don't miss the Critical Mass rides on the last Friday of every month, starting from Daley Plaza in the Loop (5:30PM). With numbers on their side, the hundreds or even thousands of bike riders wind up taking over entire streets along the way, with themed routes that are voted upon at the outset of the trip. Anyone is free to join or fall away wherever they like. Police are generally cooperative — take cues from more experienced riders.
Kayaking in urban environments is a relatively new but rapidly developing industry. Chicago is currently considered one of worlds premier self paddle destinations. Paddling companies have access points on many of Chicago's amazing beaches as well as on the Chicago River. Companies like Urban Kayaks provide unique and insightful architecture tours as well as hourly kayak rentals right downtown just minutes walking distance from some of Chicago's biggest attractions such as Navy Pier and Millennium Park.
Access to Chicago's waterways requires boat registration with the Illinois Department of Natural Resources ($13) as well as small fees that independently managed access points may charge ($5–20). The Chicago River and the area of the lake near the Chicago Lock is a carefully guarded piece of national infrastructure and the U.S. Coast Guard and CPD Marine unit are known to regularly issue citations for violating the rules. High traffic volume and other safety concerns make it advisable to visit an experienced outfitter in the area to learn about safety and proper etiquette while navigating Chicago's waterways. Most outfitters will allow users to bring their own equipment as long as it is properly registered.
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