If you want to step outside the city but stay close, here are popular day trip destinations:
Oak Park (20 min) – Tour Frank Lloyd Wright’s home and studio.
Milwaukee, WI (1.5 hr) – Known for breweries, Harley-Davidson Museum, and lakefront views.
Indiana Dunes National Park (1 hr) – Beautiful hiking trails and sandy beaches along Lake Michigan.
Starved Rock State Park (1.5 hr) – Scenic canyons, waterfalls, and hiking paths.
Lake Geneva, WI (1.5 hr) – A resort town with boat tours and historic mansions.
Longer Getaways & Multi-Day Tours
From Chicago, you can also join longer tours by bus, train, or organized group trips:
Route 66 Starting Point – Chicago is the beginning of the legendary Route 66, with tours heading southwest toward St. Louis and beyond.
Great Lakes Tours – Explore Michigan, Wisconsin, and beyond with boat cruises and scenic drives.
Niagara Falls Tours (8–9 hr drive) – Organized bus or rail tours often include stops in Cleveland or Detroit.
Amtrak Rail Journeys – Scenic train trips from Chicago to cities like New Orleans (City of New Orleans route), Seattle (Empire Builder), or San Francisco (California Zephyr).
Specialty Tours
Lake Michigan Cruises – Dinner cruises, fireworks cruises (especially during summer at Navy Pier).
Seasonal Tours – Fall foliage trips in Wisconsin or Michigan, holiday lights tours in December.
