Chicago
Times to Visit
2008 10Best Bet - Award Winners
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GOLD COAST. America's largest two-day air and water show comes back with a vengeance for its 50th anniversary. The exhibition – which often has city residents thinking bombs are about to drop from overhead – is actually a showcase of some of the hottest planes and boats in the world. As groups like the US Air Force Thunderbirds take to the skies and waters, spectators ooh and aah over the tricks of master pilots and high-speed boat captains. Keep your eyes out for stars; they usually lurk at this event.
DOWNTOWN. One should never visit Chicago without getting a healthy dose of the blues, and what better way to do it than at the official Blues Festival. This party holds bragging rights to being the largest outdoor, free blues festival the world has to offer. Have your fill of blues-inspired fare while indulging in five stages of large-scale productions and a plethora of smaller stage shows.
DOWNTOWN. Swirling melodies of jazzy tunes are almost as essential as a good ol' dose of the blues in the Windy City. Any time you hit a landmark like 30 years, you can expect the party to be all the better, so the 2008 Chicago Jazz Festival will be one not to miss. Taking place in the clean-as-clean-can-be (à la Mayor Daley) Grant Park, this jazz festival is even family-friendly.
THE LOOP. Spiced nuts, steins of beer, ginger cookies, and bratwurst mit kraut are no longer limited to Germany, thanks to this market. Add the flair of Christmas to the scene, along with booth after booth of delectable treats and original handmade gifts, and you've got a traditional München-style Christkindlmarket, right in the middle of Chicago. Shoppers can switch from the rush of Macy's to the charm of Europe, right at Daley Plaza.
Chicago has been on a steady mission to show that it can hold its own in the world of fashion. During this weeklong event, forget New York, Paris, and LA, and discover runway shows that can give them a run for their money, right in the Midwest. The real kicker is, standing room to shows and events is free and open to the public. That said, reservations are needed even for standing room. The event showcases the city's best designers, as well as up-and-coming student design stars.
GLENCOE. A showcase of some of the world's most exotic and rare species of orchids takes place each spring and fall. The competition is a sight to behold; more than 100 species of orchids vie for the Chicago Horticultural Society Award. Folks in the mood to shop should check out the amazing assortment of orchids for sale and learn about caring for the delicate plants by attending lectures and potting demonstration classes.
DOWNTOWN. Whether or not you're Irish, you'll feel the love during a very green celebration. Exhibiting not exactly an earth-friendly tone of "green," Saint Patrick's Day in the Windy City means a fully dyed green river, a noon parade from Balbo Street to Columbus Drive, live music, and plenty of "Kiss me, I'm Irish" t-shirts. Here, you may party with revelers at countless Irish pubs along the way, and even a few just claiming to be ones on this special day.
DOWNTOWN. Sure, nearly every city has a "Taste" event, but everyone knows that Chicago is a top-notch city for food-lovers. As a result, you can eat lots of things on a stick while indulging in beer, wine, or fresh fruit smoothies. With more than 70 of the city's best restaurants participating, not to mention plenty of live music, the festival promises that no one will leave the event hungry or unsatisfied. Wear comfortable everything.
MUSEUM CAMPUS. Proving that Chicago is an equal-opportunity festival host, elaborate Venetian Night is one of the city's best cultural events. Naturally, in a city where lakes appear to be oceans, the allure of water is showcased, along with numerous over-the-top yachts. Enjoy live music, fireworks, and a parade of brightly lit boats – a tradition since 1958.
WICKER PARK. Now oozing the same sort of appeal as New York City's SoHo neighborhood, hipper-than-hip Wicker Park and Bucktown comprise one of Chicago's liveliest areas. The weekend fest and sidewalk sale now bring in more than 25,000 visitors, who shop and save from a line-up of great boutiques and who enjoy live music from up to 30 bands. Oftentimes, you can't choose when you'll visit, but when you do have the option, why not let it coincide with a prominent event? Find out when the city is bursting with blooms, when holiday decorations are at their most enticing, or when a fabulously fun festival is being held. Discover, too, if there's a milestone that's being celebrated or if there's a small occasion that coincides with your own special interest. We'll spread the news and let you know when it's high time to visit the city.
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Oftentimes, you can't choose when you'll visit, but when you do have the option, why not let it coincide with a prominent event? Find out when the city is bursting with blooms, when holiday decorations are at their most enticing, or when a fabulously fun festival is being held. Discover, too, if there's a milestone that's being celebrated or if there's a small occasion that coincides with your own special interest. We'll spread the news and let you know when it's high time to visit the city. 
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