Sure, you’ve probably been to Chicago a dozen times. But the so-called Windy City has so much to see, the savvy traveler can easily make it a new experience every time.

Sure, you’ve probably been to Chicago a dozen times. But the so-called Windy City has so much to see, the savvy traveler can easily make it a new experience every time.

Fall is a fantastic season to visit, when the weather is crisp but not too cold, and the trees are brimming with radiant foliage. Read on for some of our top picks on places to see and things to do in Chicago in the fall.

Fall Is in the Air

Celebrate Halloween, Chicago-style, with Chicagoween, an annual citywide festival that brings decorations and activities to every corner of the city, from its parks and buildings to its streets. Costumed kids can march in the State Street Halloween Happening Parade and then enjoy trick-or-treating, high-flying aerial acts from the Midnight Circus, and a costume contest at Daley Plaza. Downtown also features a Haunted Village, spooky storytellers and pumpkin decorating.

Sure, you’ve probably been to Chicago a dozen times. But the so-called Windy City has so much to see, the savvy traveler can easily make it a new experience every time.

The vibrant fall colors at the Chicago Botanic Garden are sure to take your breath away. The peaceful English Oak Meadow overflows with fall-blooming flowers and several varieties of oak trees, and 100 acres of woods present a spectacular fall display.

If the brisk autumn weather has you longing for warmth, grab a chair by the cozy fireplace at Uncommon Ground, an organic-themed restaurant famous for its bowl-o-cocoa. It’s an actual bowl of rich hot chocolate topped with steamed milk, fluffy crème and omanhene chocolate, and it’s big enough to hold with two hands. While you’re there, try the hearty vegetarian chili loaded with red beans and zucchini and topped with a dollop of sour cream.

Into the Outdoors

Millennium Park breaks the mold when it comes to parks. It’s not just a downtown green space where you can soak up the serenity of nature – it also features award-winning architecture and landscape design, including the giant stainless steel Cloud Gate sculpture, known to locals as “The Bean.” The 24.5-acre park hosts world-class concerts in its Jay Pritzker Pavilion, and the interactive Crown Fountain is a big draw for kids and adults alike.

Millenium Park breaks the mold when it comes to parks. It’s not just a downtown green space where you can soak up the serenity of nature – it also features award-winning architecture and landscape design, including the giant stainless steel Cloud Gate sculpture, known to locals as “The Bean.”

Grant Park is another must-see downtown attraction. Named for Ulysses S. Grant, the park is commonly referred to as Chicago’s “front yard” due to its prominence and beauty. The park’s centerpiece is the Clarence Buckingham Memorial Fountain, and it’s the site of three popular museums – the Art Institute, the Field Museum of Natural History and the Shedd Aquarium.

And, if the weather doesn’t cooperate, you can still enjoy a bit of the outdoors.

The Lincoln Park Conservatory brings the outside in, with tropical palms, ancient ferns and thousands of plants grown for use in local parks. Stroll through the conservatory’s four display houses, showcasing palms, ferns, orchids and annual flower shows.

The Wow Factor

Check out the view from the 103rd floor Willis Tower Skydeck – you’ll never feel more on top of the world. Voted one of the “7 Wonders of Chicago” by Chicago Tribune readers, the Willis Tower Skydeck offers the best view of the city from the tallest building in the Western Hemisphere. In mid-2009, the Skydeck unveiled new window boxes made entirely of glass that allow visitors to look down through the floor at the street more than 1,300 feet below.

Check out the view from the 103rd floor Willis Tower Skydeck  – you’ll never feel more on top of the world. Voted one of the “7 Wonders of Chicago” by Chicago Tribune readers, the Willis Tower Skydeck offers the best view of the city from the tallest building in the Western Hemisphere.

Want to get an inside peek at the stock exchange? The Chicago Board of Trade’s Visitor Center opened in 2007 in the lobby of the exchange’s historic building at Jackson and LaSalle streets. Learn about the impressive and influential landmark through interactive displays on risk management, commerce development, technology and trading. You can also explore artifacts showcasing the Board of Trade’s history, videos and a retail store.

If all those numbers have you yearning for the simple life, visit the Museum of Science and Industry’s Farm Tech Exhibit, where you can challenge friends to a milking contest with a faux cow, climb on a tractor and put yourself in the driver’s seat of a real combine. This cool exhibit lets you see how farmers are using cutting-edge technologies that make farming more efficient and eco-friendly.

Want to experience even more Chicago attractions? Here are some websites to help you in planning your next trip to the Windy City.

Chicago Convention and Tourism Bureau

Illinois Bureau of Tourism

City of Chicago Tourism site

Chicago tourism site for international visitors

Chicagoland Travel

If you are into social media, consider following one of the many Chicago-related Twitter accounts. They often update with last-minute deals and discounts for Chicago accommodations, museums, events, restaurants and more. For a fairly-complete list of Chicago Twitter accounts, click here. To find even more, search #Chicago on the Twitter website.

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