The Best Day Trips From Chicago
The Best Day Trips From Chicago

The Best Day Trips From Chicago

Escape the windy city for brews and views (oh and cheese, too!) πŸ§€πŸΊπŸŒ±

Published July 08, 2021

Summertime in Chicago is nothing less than magical. But sometimes, even the most loyal city dwellers need to get out of town. Luckily, the Chi is surrounded by glorious nature, art, and beer-full cities perfect for a day trip all year around.  

Milwaukee, WI

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If you want to get out of Chicago but still need metropolis vibes, Milwaukee, Wisconsin is your answer. The city has a little bit of everything, from its famed bratwurst and beer to many riverside views. Milwaukee’s undeniable charm can be experienced through its various shops (check out Cream City Restoration for unique home decor, galleries, and restaurants. Don’t leave without eating your way through the Milwaukee Public Market or before taking a stroll along Lakeshore State Park – 22 acres of urban bliss.  

Activity Highlights Hike the 14-mile long east-to-west Hank Aaron Trail. Along the way, make sure to stop at prairies at Three Bridges Park to snap photos at the domes of Mitchell Park. 
Distance from Chicago: 1 Hour 30 Minutes 

Holland, MI

Credit: Holland.Org

No passport is needed to visit this Holland-inspired Illinois town! Named after the Dutch who settled here, Holland is a charming small town that feels cozy. There are antique windmills, unique shops, and even a Tulip Festival each Spring. The Big Red Lighthouse in Holland is one of the most impressive in the state, sitting gorgeously in contrast to the blue hues of Lake Michigan. 

Activity Highlight: For a close-up look at the windmills, spend the day at Windmill Island Gardens. Traditional Dutch performances (clogs and all!) happen here in the summer and 100% shouldn’t be missed. 
Distance from Chicago: 40 Minutes   

Michigan City, IN 

Credit: Michigan City Parks and Recreation

Michigan City is the perfect day trip from Chicago for car-less city dwellers. It’s just a quick Amtrak ride away until you’re sitting seaside on Indiana’s South Shore Line. You can also hop over into Michigan City proper to explore its best offerings like Washington Park or Old Light – one of the oldest lighthouses along Lake Michigan. Of course, there are great breweries (check out Shoreline Brewery) and comfort food here too. 

Activity Highlight: Washington Park is one of the most instagrammable spots in town. Head here for an IG-worthy photo shoot and spend time relaxing at the beachside.  
Distance from Chicago: 1 Hour 20 Minutes  

Grand Rapids, MI

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Well-known as Beer City USA, Grand Rapids Michigan is the place not only for brew lovers but also for art and food enthusiasts. Brewery-hopping is the name of the game at Grand Rapids and Brewery Vivant, a microbrewery with European-inspired beers and housed in a former historic funeral home. Each year the city hosts ArtPrize (canceled for 2021 but 🀞 it returns next year), an international art competition where art can be found all around the city, everywhere from museums to public parks.  

Activity Highlight: Create your own brewery-hopping tour by starting at Brewery Vivant in East Hill before wandering to Canal Park, where you’ll find City Built Brewing. We highly recommend indulging in their Puerto Rican eats paired with local Michigan beers. 
Distance from Chicago: 3 Hours 

Indiana Dunes National Park, Indiana 

Credit: Indiana Dunes

Often considered one of the coolest national parks in the midwest, Indiana Dunes is worth the trip from Chicago no matter the time of year. A true nature lover’s paradise, there are over 15,000 acres of beaches, hiking trails, prairies and more. It’s easy (and highly recommended) to spend all day here. 

Activity Highlight:  While exploring Indiana Dunes, you shouldn't skip over Pinhook Bog, a unique wetland covered in rare flora and fauna. Don’t forget to make a reservation for this ranger-guided experience. 
Distance from Chicago: 50 minutes

Monroe, WI

Credit: National Historic Cheesemaking Capital 

Get in, we’re going to the Swiss Cheese Capital of America! Monroe is a cozy town where cheese lovers should indulge in the many cheese-related activities offered here. There are many cheese shops to explore, but the best place to get up to speed on cheese history is the National Historic Cheesemaking Center. After, spend the evening strolling before heading to Minahs, a local brewery for a beer and cheese pairing. 

Activity Highlight: For more cheese-tivities, head to Roth creamery to sample delicious Wisconsin cheese and have the delectable treat in it's second best form – grilled cheese. 
Distance from Chicago: 2 Hours 30 Minutes 

Cedarburg, WI

Credit:Washingon House Inn

Need to decompress from city life? Wind down in Cedarburg. The locals take things slow in this small town. You’ll spend your days wandering exhibitions at the Cedarburg Art Museum or sipping wine at the Cedar Creek Winery – whatever you do, take it easy here. 

Activity Highlight: Cedarburg’s downtown is quaint and perfect for afternoon strolling. Go shopping at the many boutiques along Washington Avenue. 
Distance from Chicago: 2 Hours 

Oglesby, IL

Credit:Oglesby, IL

Nature lovers will adore this city break from Chicago. Oglesby, Illinois is home to two state parks, and they surely don’t disappoint. Spend the day beneath clear air at Starved Rock State Park (the views are endless). Or head to the less famous – but equally beautiful – Matthiessen State Park, where you’ll find pristine hiking trails and waterfalls.  

Activity Highlight: At Starved Rock, hop on a river cruise or choose from 13 miles of hiking trails. And at Matthiessen, choose from 5 miles of courses ranging from relaxed to various hikes. 
Distance from Chicago: 1 Hour 40 Minutes 

Lake Geneva, WI

Credit: Visit Milwaukee

Resting on Geneva Lake, this is an ideal vacation spot for many Chicagoans. Lake Geneva, Wisconsin, was made for summer with endless water sports like kayaking and wake surfing. For the few moments when you’re not on the water, the town center has simple local food fare and even a popular waterfront champagne brunch in a 19th Century Mansion style hotel. 

Activity Highlight: Head to downtown Lake Geneva for Flat Iron Park, antique shopping, and cocktails at Fat Cats. 
Distance from Chicago: 1 Hour 35 Minutes 

Highwood, IL 

Credit: Visit Lake County

This small Illinois town is big on festivals! Just a short drive north of Chicago, Highwood is a charming town with festivals of all kinds nearly every month. From foodie festivals like their taco fest to obscure ones like the Garlic Festival, there’s truly something for everyone here. To get an authentic feel of Highwood’s culture, visit during October when their most iconic festival, The Great Highwood Pumpkin Festival, kicks off. 

Activity Highlight: Coming during Pumpkin Fest season is a must. For the best experience, we recommend planning your trip for the entire festival weekend. 
Distance from Chicago: 40 Minutes 

Madison, WI 

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One of the best day trips from Chicago is Madison, Wisconsin. It’s a great place to visit time all year round, but the summers are extra magical. With five lakes, the city seems to have an endless supply of watersports and waterfront dining. Beer lovers should tap into the many breweries and delicious restaurants in Madison. 

Activity Highlight: While exploring Madison’s waterfront, be sure to make a pit stop at Olbrich Botanical Gardens, where exotic foliage is always in bloom. 
Distance from Chicago: 2 hr 20 minutes

Rockford, IL

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Rockford is the fourth largest city in Illinois, and it feels like a big little city. Bursting with things to do, daytrippers should be sure to explore the Anderson Japanese Gardens, an urban oasis full of breathtaking blossoms. For families, the Discovery Center Museum is a must-visit for 300 other art exhibits to explore. Spend the afternoon at Prairie Street Brewing Company for a unique twist on usual bar food (Hello Koren street tacos), and of course, local brews. 

Activity Highlight: If you’re looking for more art adventures following the Discovery Center Museum, head to Rockford Art Museum to look at their century-old art collection. And just south of downtown, more nature walks await at the Klehm Arboretum and Botanic Garden. 
Distance from Chicago: 1 Hour 30 Minutes 

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