Day Trips from Chicago: Oak Park, Milwaukee & Indiana Dunes
The best day trips from Chicago are close and easy without a car. Oak Park, 20 minutes west on the Green Line, has the world’s largest collection of Frank Lloyd Wright buildings, including his Home & Studio and the Unity Temple; Robie House in Hyde Park is the Prairie-style masterpiece. Milwaukee is 90 minutes north on the Amtrak Hiawatha for breweries, the lakefront art museum and a Third Ward food tour. Indiana Dunes National Park is an hour east on the South Shore Line for beaches and dune hikes with the skyline on the horizon. With a car, add Starved Rock State Park’s canyons (90 minutes) or historic Galena (about 3 hours). Bookable tours and tickets for each are compared below.
167 tours · prices per person, book with partner
Day Trips from Chicago in Chicago — FAQ
What are the best day trips from Chicago?
Oak Park for Frank Lloyd Wright architecture, Milwaukee for breweries and the lakefront, Indiana Dunes National Park for beaches and hiking, Starved Rock State Park for canyon trails and Galena for a historic small town. Oak Park, Milwaukee and the Dunes are all reachable by train.
How do you get to Oak Park from downtown Chicago?
Take the CTA Green Line to Oak Park station, about 20–25 minutes from the Loop, or the Metra UP-West line. Frank Lloyd Wright’s Home & Studio and the historic district are a short walk from either station; guided and self-guided tours run daily.
Is Milwaukee worth a day trip from Chicago?
Yes — the Amtrak Hiawatha takes about 90 minutes each way, and a day covers the Historic Third Ward, a brewery tour, the Milwaukee Art Museum on the lake and a food tour. Guided Milwaukee sightseeing tours start downtown near the station.