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Chicago’s handy grid system makes navigation a breeze and most downtown tourist attractions are within walking distance of each other. The CTA transit system is relatively straightforward and if you can’t face walking in that infamous wind, taxis are everywhere – just get your thumb ready to flag them down local-style. When it comes to weather, the spring (April - May) is a sweet spot. Clear skies are a common sight and there’s far less wind and rain than usual. Hotels are often cheaper then too, due to fewer crowds.
Pizza Pizza Pizza
Chicago-style deep-dish pizza is one of the city’s main claims to fame. And rightly so: it’s amazing! For one of the best authentic Chicago pizza experiences, head to The Art of Pizza, an institution thanks to the thick, tomatoey, herby special sauce. For more stringy mozzarella madness, try the deep-dish slices at Giordano's – there are lots of branches around the city. ODed on pizza? For burgers worth lining up for, head to Brendan Sodikoff’s Au Cheval and don’t forget to add some thick-cut peppered bacon.
Jazz, Blues & Musical News
Chicago’s legendary blues and jazz can be enjoyed in endless venues all over the city, but there’s music for all tastes here. Massive concert halls such as The Chicago Theatre or Aragon Ballroom are always hosting great artists, and new acts can be discovered at clubs like Empty Bottle and Metro. Schubas Tavern and The Hideout are cosy spots for catching live tunes. The Chicago Blues Festival in June, and the Chicago Jazz Festival, on Labor Day weekend are high times for music buffs to hit the Windy City.
360 CHICAGO Observation Deck
Climb your way to the skies of Chicago in one of America’s fastest elevators! At 360 Chicago (in downtown Chicago's John Hancock Center) you’ll be 94 floors high, so imagine those views. See the new Chicago Interactive History Exhibit featuring quotes from city fans and famous residents like Oprah Winfrey. If you’re brave enough, experience TILT, Chicago's highest moving experience, which literally tilts you towards the ground for even more views of the city, Lake Michigan, and four neighboring states - Wisconsin, Michigan, Indiana, and Illinois.
Packed full of sculptures and flowers, this 24.5 acre park in the Loop makes a great place for unwinding after a day of sightseeing. There’s live music on weekends, an ice-rink in the winter, and even an outdoor rock climbing gym. Don’t miss Anish Kapoor's Cloud Gate (a.k.a. “The Bean”), a rather odd reflective sculpture shaped like a kidney bean. Jaume Plensa's Crown Fountain is just as odd. Here you’ll see changing faces on a big screen, all spitting out water! For great views of Chicago take the pedestrian bridges to the Art Institute and Maggie Daley Park.
River & Lake Architectural Cruise
See the windy city from the water on a speedboat! With a River & Lake Architectural Cruise you’ll get to snap all the city highlights while your native guide explains exactly what you’re looking at. See the Tribune Building, Willis Tower, Lyric Opera and more as you pass lakefront properties and cruise through the famed Chicago Locks. It’s one of the best ways to see the city and if it’s extra windy out there on the river, your boat will go even faster – win-win!
The Magnificent Mile
A mile of magnificence is what Chicago promises, and its Magnificent Mile stretches from the Chicago River to Oak Street in the Near North Side. There's an abundance of boutique shops, 300 restaurants, 60 hotels and iconic architectural feats, including the Wrigley Building, Tribune Tower and the John Hancock Center. You’ll also see a few survivors of the Great Chicago Fire (1871) like the Historic Water Tower and the Pumping Station.