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The Best of Fall in Chicago

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Chicago's festival scene heats up in the fall with beer, pumpkins, and nightlife. Oktoberfest and the Design Harvest Festival happen within days of each other in September, the Highwood Pumpkin Fest and Halloween costume parades take up all of October and November has a Turkey Trot followed by lighting the Christmas tree in Daley Plaza. The best of fall is often the best of Chicago.
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West Town, Chicago, IL, USA
The annual Design Harvest festival brings more than 50 vendors to West Grand Avenue. Oversize tents fill up with metal sculptures, handmade messenger bags, and beautiful wooden furniture by Chicago designers such as Jason Lewis. September 29–30....
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600 E Grand Ave, Chicago, IL 60611, USA
Most visitors to Chicago see it from only one perspective: from the city looking out over the water. But what would it look like if your vantage point was from out over the water looking down at the city? Just a little bit north of Chicago there...
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Boystown, Chicago, IL, USA
If you're in Chicago on Halloween, head to Boystown for the Northalsted Halloween Parade. The annual parade along Halsted, the beating heart of Chicago's gay community, brings out fire twirlers, drag performers and some of the city's best...
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Illinois Medical District, Chicago, IL, USA
Chicago is the king of comedy, hot dogs, and extreme Midwest weather. But since the Great Chicago Fire of 1871, the city has been reinventing itself. Today, clever design projects (such as “Color Jam,” shown) top the list of reasons...
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50 W Washington St, Chicago, IL 60602, USA
When the Christmas tree lights up the Daley Plaza, it’s a magical moment every year. Chicago’s tree lighting ceremony includes live music and theatre performances by the actors in A Christmas Carol and officially begins the holiday season in late...
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1 N Michigan Ave, Chicago, IL 60602, USA
If you're visiting Chicago in the winter, be sure to make your way to one of the city's many ice rinks. For outdoor skating with a view, head to the McCormick Tribune Ice Rink in Millenium Park. The ice skating rink is sandwiched between Cloud...
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Chicago, IL, USA
Beer lovers celebrate Chicago's fall season with German festivals all through September and October. Hofbrauhaus restaurant on Rosemont brews their own special Oktoberfestbier while an Austrian Oompah band plays nightly, deca restaurant at the...
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175 N State St, Chicago, IL 60601, USA
Chicago has wonderfully rich theater scene ranging from intimate storefront theaters to the famous improv comedians at Second City and any number of Broadway shows. The Cadillac Theatre in the Loop has a beautiful, richly decorated house for large...
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99 Chicago Riverwalk, Chicago, IL 60601, USA
Catch this unique experience twice a year - a couple of weeks in April and October when each of the 20+ movable bridges over the Chicago River open in succession to let the sail boats out to or in from their Lake Michigan marinas for the summer...
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1215 IN-49, Porter, IN 46304, USA
Just a 45-minute drive from the Chicago’s downtown Loop, 200 foot sand dunes tower over the wild untrammeled shores of Lake Michigan. The Indiana Dunes State Park has 2,000+ acres of wilderness crisscrossed with hiking trails and camping spots and...
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Galena, IL 61036, USA
Illinois has no less than 6 wine trails running the length of the state and extending into Michigan and Wisconsin. More than 450 vineyards and 100 wineries are available to visit or tour and range from small boutique establishments to large...