- Question: What makes Chicago a great starting point for day trips?
- Answer: Chicago is nicely placed for a number of day trips, being connected to some beautiful locations by train.
- Question: What are some options for day trips from Chicago?
- Answer: If you're living in Chicago or visiting the city and looking to spend a day somewhere different, here are some of the best day trips you can take from Chicago by train.
Best Time for Day Trips from Chicago by Train:
- April to June – Enjoy blooming parks, lake views, and charming small towns along scenic rail routes.
- July to August – Perfect for beach towns, summer festivals, and cultural hubs just a short ride away.
- September to October – Ride through fall foliage to historic villages, wineries, and nature escapes.
- November – Cooler weather ideal for cozy cafés, museums, and holiday shopping in nearby cities.
- December to March – Winter train trips to festive markets, snowy getaways, and indoor attractions.
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1. From Chicago to Milwaukee
Visit historic breweries and walk along the scenic Lake Michigan shoreline.
Milwaukee is less than two hours away from Chicago by Amtrak and it's one of the best places you can choose for your day trip. Yes, it's a big city location just like Chicago, but it's a very different kind of place. There are plenty of unique experiences to be had in Milwaukee, and the pace of life is a little slower and more subdued than the Windy City's.
Popular things to do in Milwaukee include visiting the Art Museum and the Harley-Davidson Museum. A trip to the Mitchell Park Horticultural Conservatory is always worth one's time as well, and a walk along the side of the Menomonee River is particularly enjoyable for families and couples alike.
2. From Chicago to Oak Park
Explore Frank Lloyd Wright’s architecture and admire charming historic homes.
Oak Park is one of the closest locations to Chicago for a day trip. In fact, you can get to Oak Park by train in about 40 minutes, so it's a great spot to choose for people who don't really like long journeys or don't want to have to get up really early just to make the most of their day.
Best known as the home of famed architect Frank Lloyd Wright, Oak Park is a really pretty place with a lot to offer. You can enjoy a full Frank Lloyd Wright tour, visiting the architect's former home and studio, as well as passing by some of the beautiful houses he helped create. There are some quality craft beer bars and decent restaurants to be found in Oak Park as well, so it's great for a relaxing day out.
3. Day Trip to Michigan City from Chicago
Relax on sandy beaches and visit the lively outlet malls for a quick trip.
The journey from Chicago to Michigan City takes a little over an hour by Amtrak, and it's well worth the trip. This unique city sits on the south shore of Lake Michigan, so it's one of the best options for anyone seeking a Great Lakes day trip outside of Chicago. You can get direct Amtrak trains from Union Station to Michigan City, and the journey is quite scenic and picturesque.
Once you arrive at Michigan City, you can explore and experience some of the various attractions like Washington Park Zoo, the Old Lighthouse Museum, and the always-impressive Barker Mansion. Otherwise, if you're just in the city to lie back and relax, you can head down to the beach and admire the amazing views all around you.
4. Kalamazoo from Chicago
Discover vibrant craft breweries and explore unique local museums.
Head over the state line into Michigan for a day trip to Kalamazoo. You can take the Amtrak to this beautiful, artistic city, with the journey taking around two hours in total. There are several daily trains running right to Kalamazoo, leaving early in the morning and setting back late in the evening, so the timings are always right for a day trip.
Kalamazoo is a very inspiring place that holds a lot of appeal for poets, artists, and other creative people. It's also home to some interesting attractions including the Air Zoo aircraft museum, the Kalamazoo Valley Museum, and the Gilmore Car Museum. It's also a great spot for foodies, home to some of the best restaurants and bars in Michigan, with plenty of local craft breweries to visit too.
5. Day Trip to Libertyville from Chicago
Walk along charming downtown streets and visit scenic forest preserves.
Another popular day trip option from Chicago by train, Libertyville is a small village in Lake County, Illinois. It's a charming place with very friendly locals, offering a great escape from the big city streets. The journey from Chicago to Libertyville by train only takes about an hour in total.
You won't find too many major attractions or monuments in Libertyville, but it's a lovely location for those who just want a calm and pleasant day out of the city. There are some super bars and restaurants here, as well as a great range of boutiques and small stores. The local movie theater is quite a popular hangout spot too.
Plan Your Trip
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