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Last-Minute Fall Day Trips

Posted on November 19, 2025
Emily Mack

Emily Mack

Morton Arboretum

Fall foliage at the Morton Arboretum. (Raymond Boyd/Michael Ochs Archives/Getty Images)

Sure, the trees might be looking a little barren, but it’s not too late to go on an autumn adventure! I promise! Whether you’re traveling by car or by train, near or far, we’ve got you covered.

City Cast

There's a Perfect Fall Road Trip in Every Direction from Chicago

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Across State Lines

A DIY Frank Lloyd Wright Pilgrimage

Chicago boasts several Frank Lloyd Wright structures, but the architect was Wisconsin bred. Explore his legacy in his home state, starting in Racine, working your way up through Madison, and eventually ending at Taliesin, Wright’s house-studio in Spring Green.

  • 🏚️ House on the Rock is also right by Spring Green — a Midwestern must-see.
  • ☕ Stop at Tan-a-Latte in Jefferson along your route. You can get a sun-kissed glow while waiting for your PSL.

Milwaukee, Wisconsin

Rev up at the Harley-Davidson Museum, drink up on a beer history tour through Pabst (you will get free brews if you pay attention), or smoke up at the haunted Shaker’s Cigar Bar … and maybe crash at the brothel-turned-Airbnb upstairs.

City Cast

Hop Aboard Metra for Quick, Cheap Fall Day Trips

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Closer to Home

The arboretum in Lisle has miles of hiking trails, art exhibits, a library, and special events all year long. Right now, Illumination: Tree Lights at The Morton Arboretum is running through Jan. 3.

  • 🚂 Morton Arboretum is about two miles from the Lisle stop on the Metra BNSF line.

Keep your day trip in city limits in Pullman — the district officially became a National Historical Park in 2022, dedicated to the labor movement. Now that the government shutdown is over, park rangers are back and the park is in full swing. Start at Exhibit Hall, which highlights the neighborhood’s history.

  • 🚂 Pullman National Historical Park is right off 111th Street on the Metra Electric Line — you can see the landmark clock tower from the train window.
👻 Fancy a haunted road trip?

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