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Top 3 Day-Trip Locations From Chicago, IL

Apr 9, 2018
by Danny Brown

Whether you’re trying to look for a small town to unwind and relax in, or a beach-side community for hiking, hang gliding and kayaking, you can count on the combo of South Bend, IN, Harbor Country, MI, and Cedarburg, WI which are all located within close proximity to Chicago, IL. Their locations may be across 3 different state lines, they are easily accessible via a charter bus.

There are art center, brewing companies and wineries, sports stadiums and botanical gardens here for you to explore and have a blast in with your loved ones. With the following attractions in neighboring cities, it's almost a given that your spring and summer vacation is going to be absolutely unforgettable. 

sunset over lake, day trips from Chicago IL

1. Explore The Cultural Side of South Bend, IN

Located slightly less than 2 hours’ drive via I-90 W
Fun-filled, culturally-diverse and a food haven for even the pickiest eaters in your group, the fourth largest city in the state of Indiana is only a short charter bus ride away from downtown Chicago, IL. This awesome Midwest city is perfect for families, single travelers, and groups alike, whether you’re in it for a relaxing weekend or days of gripping adventure!
  • Four Winds Field at Coveleski Stadium
    501 W South St, South Bend, IN 46601
    (574) 235-9988

    The stadium is home to the South Bend Cubs, a minor league baseball team affiliated with the Chicago Cubs, and has been regarded as "the grandfather of modern ballparks" by Thanks to its many renovations, it is one of the most family-friendly sports facilities in Indiana. You can let the kids roam and jump around in the baby stadium while you feast on the endless array of food and drinks from the concession stands during a game.
  • The Indiana Whiskey Company
    1115 W Sample St, South Bend, IN 46619
    (574) 520-1915
    A strong advocate for using locally-sourced ingredients like wheat, barley, and corn to produce delicious and crafty whiskey, they are run by vets who offer free shots of their delicately-brewed whiskey as a welcome gift. They also offer tours, organizes special events and its wonderful, spacious venue is also up for rental.
  • Basilica of the Sacred Heart
    1 Holy Cross Dr, Notre Dame, IN 46556
    (574) 631-7329
    There are very good reasons why this is regarded as one of the most beautiful university churches in the world and you'll see it with your own eyes the moment you step out of the charter bus. A tour guide will take you around to explain the many iconic and historic structures in this place of worship. The picture-perfect neo-gothic backdrop makes it perfect for weddings, mass and the 44 large stained glass windows, ornate decor, murals and 218-feet basilica bell tower deserves to be in your pictures. The church took approximately 17 years to decorate.
  • Morris Performing Arts Center
    211 N Michigan St, South Bend, IN 46601
    (574) 235-9190
    Saved from demolition, the theater was originally known as both Palace Theater and Morris Civic Auditorium which was built as part of the Orpheum Theatre chain. J.S. Aroner envisioned the theater as a ‘little palace’, hence, the rose, blue and cream color scheme is extremely soothing to the eyes. Having withstood the test of time and potential destruction, it continues to be an elegant place that can transport patrons down memory lane.

2. Discover The Adventurous Sides of Harbor Country MI

A stone’s throw away from Grand Beach, Long Beach, New Buffalo and Union Pier, Harbor Country, as the name might suggest, is a convenient weekend getaway destination within a short drive from Chicago, IL. The town center is upscale and strewn with bed and breakfasts, chic hotels, affordable motels, wineries and has a vast array of attractions for cross-country skiing, pumpkin-picking, wine tasting, birding, biking, golfing and hiking. 

  • Greenbush Brewing Co.
    5885 Sawyer Rd, Sawyer, MI 49125
    (269) 405-1076
    It boasts of great food like roast beef, sandwiches, BBQ, pulled pork, cool vibe, and 12 types of on-tap ice cold glasses of craft house-brewed beer. It is open from Sunday to Thursday 11.30am - 10pm, Friday and Saturday 11.30am - 11pm. A tidy little corner is reserved for your little ones to play in while you chat away with your friends over the great food and drinks.
  • New Buffalo Farmers Market
    910 W Buffalo St, New Buffalo, MI 49117
    (269) 449-1695
    The quaint farmers market is open every Thursday from May through to September and sponsored by the New Buffalo Business Association. Just head over to N Whittaker and Merchant Streets in downtown New Buffalo and you can shop to your heart’s delight for artisan food, seafood, cheeses, desserts, coffee, clothing, antique and second-hand items, then enjoy live entertainment before calling it a day. 
  • Geocaching at Fernwood Botanical Garden
    13988 Range Line Road, Niles, MI, 49120
    (269) 695-6491
    Open to the public, Fernwood Garden is the perfect place for the fun and games of geocaching because it has more than 100 acres worth of green space for the hunting. All you need is to get in touch with experienced people like the GeoCats group who are already familiar with the all-new modern-day scavenger hunt in the garden. Hang onto your smartphone, load up your GPS and get ready to discover treasures hidden in caches and containers in the greens of the garden.
  • Warren Dunes State Park
    12032 Red Arrow Hwy, Sawyer, MI 49125
    (269) 426-4013
    Harbor Country boasts of miles of shore along Lake Michigan and the beaches that it brings us. It is, indeed, the pride of Harbor Country! Warren Dunes State Park is, doubtlessly, the number one spot for hang gliding over the lake, snowboarding, cross-country skiing, walking, hiking, camping, picnicking, eating, drinking and, of course, beach bumming! The park is open all year round from 8am to 10pm and has well over 200 dune campsites and rentable mini cabins up for grabs.

3. Cedarburg, WI

If you need to slow down the tempo and just chill out with your family and friends, you don’t have to go far. Located slightly less than 2 hours and 30 minutes away from Chicago, IL, is the ever-charming, old-school Cedarburg, WI, 20 miles north of Milwaukee. Cedarburg boasts of seasonal events, old-world traditions, culture, cuisine and unique architecture. Friendly Midwesterners are always waiting with wide open arms to bring you events like the Cedar Brew Fest, Cedarburg Christmas, and the Strawberry Festival when you visit. 

  • Ozaukee Interurban Trail
    Get on a bike and ride along the shores of Lake Michigan, stop by a Legion Post, have a beer with a local Vet while trekking your way around this amazing trail. The Ozaukee Interurban Trail connects historic downtowns, woodlands, wetlands, farmlands, Milwaukee River, Lake Michigan and skiing and cross-country trails and would quickly quench your thirst for the great outdoors.
  • Cedarburg Art Museum
    W63 N675 Washington Ave, Cedarburg, WI 53012
    (262) 377-6123
    Originally intended as a gift from father, Diedrich Wittenberg, to his daughter and her new husband, the grand, red brick building, designed intricately in Queen Anne and Romanesque style, features everything from cool masterpieces of local artists to little art rooms for the little ones. When it is not running classes like Modernism for Kids and Mindfulness: The Art of Living, it showcases curated artwork from local artists and those from its surrounding communities.
  • The Fermentorium
    7481 State Road 60, Cedarburg, WI 53012-9702
    (262) 421-8593
    When you’re done touring the city while checking out quaint stores and dropping by the art museum, you could be ready for a drink. And for this, there’s always The Fermentorium along State Road 60. The casual, relaxed and inviting vibe around the tasting room makes it an awesome place to meet up with your friends over a few drinks and bar grub. Relatively quiet on weekdays, you can expect things to be a little bit more hyped up during Saturdays even when families bring their children in for board games and kid-friendly activities.

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