If you’re looking to escape the hustle of Chicago for a quick weekend, several destinations within a few hours can provide a refreshing change of scenery. With a wealth of options accessible by train, bus, or car, you can easily make the most of your precious time off.
Within a short drive or train ride from Chicago, you’ll discover charming towns and vibrant cities, perfect for a brief getaway. One standout option is Milwaukee, just 90 miles away. You can take the Amtrak Hiawatha Line from Union Station for $24 one-way, arriving in about 90 minutes. Once there, you’ll find lively breweries, like Lakefront Brewery, where tours are around $12 and include tastings of their famous beers.
Another great choice is the picturesque town of Galena, located about 160 miles from Chicago. If you drive, it takes about three hours. Galena boasts historic architecture and scenic views, particularly along Main Street, where you can explore quaint shops and art galleries. For a unique dining experience, don’t miss the Fried Green Tomato restaurant, offering Southern-inspired dishes at reasonable prices.
Milwaukee is renowned for its breweries and Lake Michigan waterfront. After arriving, consider visiting the Milwaukee Art Museum, famous for its stunning architecture. The admission fee is $19, which grants access to a diverse collection of artworks. For a leisurely afternoon, stroll through the Historic Third Ward, where you'll find boutiques and eateries, including the Milwaukee Public Market, featuring fresh local ingredients. Grab a bite at St. Paul Fish Company, where you can enjoy a delicious fish sandwich for about $12.
In the evening, dive into Milwaukee’s brewery scene. Head to Good City Brewing located in the East Side neighborhood, where you can sample their signature brews like the “Hazy IPA” for around $6 per pint. If you're in the mood for some live music, check out The Pabst Theater, which hosts a variety of performances and typically has tickets ranging from $20 to $50.
Galena, known for its well-preserved 19th-century buildings, is a delight for history buffs and nature lovers alike. Once you arrive, explore the Galena History Museum to learn about the town’s role during the Civil War. The entrance fee is $10. For an outdoor excursion, hike along the Galena River Trail, which offers stunning views and is an easy walk for all levels.
Culinary options abound in Galena, with local favorites such as the Galena Brewing Company. Here, you can savor a pint for around $5 while enjoying a view of the river. Don’t miss out on the local cheese shop, Galena Cheese Company, where you can sample artisanal cheeses and buy some to take home. Galena also has a vibrant arts scene, so make sure to check out local galleries and crafts shops along Main Street.
Maximizing your short trip from Chicago requires some planning. Here are a few tips to ensure a smooth experience.
| Item | Cost | Notes |
|---|---|---|
| Amtrak Hiawatha ticket (one-way to Milwaukee) | $24 | Departs from Union Station |
| Milwaukee Art Museum admission | $19 | Art exhibits and stunning architecture |
| Lakefront Brewery tour and tasting | $12 | Learn about the brewing process |
| Galena History Museum admission | $10 | Explore local history |
| Fish sandwich at St. Paul Fish Company | $12 | Casual dining option |
| Pint at Good City Brewing | $6 | Sample local craft beer |
| Galena Brewing Company pint | $5 | Enjoy local brews with a view |
Use this rough planner to sanity-check the total trip cost before you lock flights, hotels or activities.
The best time to visit Milwaukee and Galena is during the spring and fall months. From May to October, you’ll experience warmer weather and plenty of outdoor festivals. Fall is particularly stunning in Galena, where you can witness vibrant autumn foliage.
You have several options to travel from Chicago to Milwaukee and Galena. For Milwaukee, take the Amtrak Hiawatha Line, with service every couple of hours. For Galena, driving is the most convenient, but you can also consider taking a Greyhound bus, which takes around 3.5 hours, with tickets typically costing $25-$35.
Traveler comments
Add a route note, correction, timing tip or question for this guide.