Best Day Trips from Chicago

by Karrie Fuller, PhD | Jul 10, 2023 | Chicago, Exploring Chicago

While you won’t run out of activities to do in Chicago, sometimes a change of scenery is good for the soul. The landscapes surrounding the Windy City range from urban and suburban, to agricultural and straight up wilderness, and this variety means that Chicago residents can, even on a whim, embark on a short journey that matches their mood in the moment. Moreover, you don’t need to limit your excursions to the summer months. Fun activities outside the city happen year round, so don’t let winter keep you stuck at home.  

Whether you need some fresh air in the great outdoors, or want to experience small town America for yourself, we’ll send you off on some daylong adventures you won’t soon forget.

Related: Where to Find Italian Groceries

Fun Road Trips from Chicago

Chicago is a big city, and the distance and drive time to these places will depend on where, exactly, you live. So, we chose the Loop, near the Art Institute, as our starting point, and we chose only places that you can arrive at in under 2 hours from this point. Afterall, we want you to have plenty of time to make the most out of your day trips from Chicago.

Day Trips from Chicago: Cities & Towns

Oak Park, IL

Approximate Drive Time: 30 minutes

Distance: 9.5 miles

Architecture lovers and Frank Lloyd Wright fans unite in their passion for touring the visionary’s buildings throughout Oak Park, IL, including his own home and studio. For the literary-minded among us, Ernest Hemingway’s Victorian birthplace home, the first in the village to get electricity, awaits your visit. And, if you can’t resist a good nefarious historical outing, stop by Al Capone’s gravestone to pay your respects.

Although Oak Park prides itself on its history and architecture, you can discover plenty of great food and fun to pair with your more educational adventures. Popular restaurants, such as Maya del Sol and Il Vicolo Trattoria, provide a wide variety of dining options. Cute shops, bakeries, and even a children’s museum add to the charm of this village on Chicago’s border.

Evanston, IL

Approximate Drive Time: 40 minutes

Distance: 14 miles

Sitting on Chicago’s northernmost border, with Lake Michigan defining its eastern edge, this urban suburb is easy to get to by train or car. As Chicago’s neighbor and home to the well-reputed Northwestern University, the Windy City spills over into parts of Evanston, bringing with it some of Chicago’s perks – food, culture, and even the people (many Chicagoans move there when they buy a home).

If you want to spend a day getting to know a new city, you could do worse than a tour of Evanston. The museums, such as the Block Museum of Art, as well as Grosse Point Lighthouse, beaches, street fairs, and shopping districts will keep you busy. Our favorite shops include Bookends & Beginnings, The Alchemist’s Wife, and Ten Thousand Villages. As for food in Evanston, you can’t go wrong at Hewn, La Cocinita, or Tapas Barcelona.  

Kankakee, IL

Approximate Drive Time: 1.5 hour

Distance: 61 miles

Head south for a while, and you will land in Kankakee, IL, a small city with two Frank Lloyd Wright homes and a historic courthouse built in the Neoclassical style popular at the turn of the 20th century. Representing a blend of old and new, you can visit numerous historical buildings and museums, including churches with gorgeous stained glass windows. Take advantage of the more modern activities as well, from outdoor festivals to indoor axe throwing.

Golfers will rejoice at the number of clubs and courses in the area, while outdoor enthusiasts will get dirty exploring the nearby Kankakee River State Park, which offers fishing, camping, cycling, and more. The Merchant Street Music Festival brings in visitors from all over the state, and the local breweries will keep you happy throughout the evening (Brickstone and Knack Brewing are great starting points).

Milwaukee, WI

Approximate Drive Time: 1.75 hours

Distance: 100 miles

Milwaukee is Chicago’s sister city, still urban, but less overwhelming and with more of a small town feel in comparison. Like Chicago, Milwaukee displays its rich history in the old buildings that make up much of the downtown area. The attractions, both old and new, along with the creative local food and shops make the short drive here worth it. The stunning Milwaukee Art Museum that sits right on the Lake will impress you with both its architecture and collections. To fuel your wilder side, the Harley-Davidson Museum provides great family fun. And, the beaches, riverwalk, and parks offer some outdoor adventures, with cultural enrichment in every sculpture and mural you encounter along the way. Shopping in the Historic Third Ward and the Milwaukee Public Market will give you a literal taste and feel for the culture Milwaukee’s energetic entrepreneurs engender.

Also like Chicago, Milwaukee tries to hoard as many James Beard nominees and winners as it can. They serve up award-worthy food at restaurants throughout the city, and you can’t go wrong with any of them. Try one, and you’ll plan more day trips here as an excuse to taste the rest. Start with DanDan for Chinese-inspired cuisine, Amilinda for flavors that hail from Spain and Portugal, or Bavette La Boucherie for a neighborhood butcher and farm-to-table restaurant. Don’t ignore the diverse cultures represented in the lineup of great Milwaukee restaurants as well – Alem Ethiopian VillageGuadalajara Restaurant, and Momo Mee will serve you well. Don’t head home just yet though, finish your day at Purple Door Ice Cream, and you will drive back with a smile on your face.

Lake Geneva, WI

Approximate Drive Time: 1.7 hours

Distance: 83 miles

A popular and quick getaway spot for Chicago residents, Lake Geneva will serve as your go-to lakeside retreat. Here, you can choose to connect with nature, pamper yourself at the spa, meander through museums, golf, shop, fish, and do just about anything you might want during your day of escape. From a waterpark, zip-lining, and a safari, to horse riding, arcade play, and ghost tours, you won’t run out of creative activities that will bring out your sense of adventure. Take a ride with the East Troy Railroad Museum, stargaze from Yerkes Observatory, or cruise the lake on a boat tour. 

Once you work up an appetite, dine and drink your way around town. The Italian-American Sopra Bistro, run by a former Chicago chef, caters to Windy City visitors. Or, take your dinner party to the patio at Oakfire Pizza, where you can soak in the summer breeze and munch on Neapolitan-style wood-fired pies. Go glam in a Victorian-era mansion for fine dining in a historical setting at The Baker House. Plus, you can take in more history at a neo-Gothic church built over a century ago when you simultaneously quench your thirst and experience heavenly enlightenment at the Topsy Turvy Brewery. Finish your meal with dessert at Lake Geneva Pie Co. for some, well, you can guess.

Michigan City, IN

Approximate Drive Time:  1 hour

Distance: 60 miles

Instead of sticking to the state of Illinois, or driving north for good ol’ Wisconsin, you can head southeast to the Lake Michigan coast in Indiana. City dwellers journey to Michigan City for the lakefront beaches. Make the most of the water with Harbor Country Adventures’ boat tours and water sports. Or, to soak in some history, explore the lighthouse and The Barker Mansion, and then become a pioneer in the early 1800s at Pioneer Land. Pick berries and gaze at flowers at the nearby orchards, farms, and gardens as you acquaint yourself with the Indiana landscape. And, shop at the large outlet mall, or at the many antique shops in town, depending on your interests.

For food and drink, start your day with caffeine at Fluid Coffee Roasters, followed by brunch at Bare Bones Gastropub. Farina’s Supper Club serves up Italian classics made by former Chicago star, Chef Joseph Farina, and Cool Runnings Jamaican Restaurant diversifies the city’s menus with popping Jamaican flavors. This area contains many nearby breweries, such as Burn ‘em Brewing, but they also ferment their own grapes at Shady Creek Winery, a fine way to top off your beach day. 

New Buffalo, MI

Approximate Drive Time: 1.25 hours

Distance: 71 miles

Continue following the Lake Michigan coast, and you hit the southwest border of Michigan, with its cute beach towns, exceptional breweries, and fruit-picking paradises. Water-related activities in a cute, small town setting bring visitors to this stretch of the shoreline. A great weekend farmer’s market during the warmer months coupled with antique shops for anyone looking to spend money round out its character. For lovers of Las Vegas, you can get a temporary casino fix at Four Winds Casino. They also offer golfing, park concerts, and a railroad museum to entertain visitors.

Drink and eat at Beer Church Brewery, named for its location inside a former Methodist church. People come from all over the region to dine on their wood-fired pizzas and swallow pints of their standout craft beers. David’s Delicatessen & Coffee will serve you well for breakfast and lunch – grab your food to go so that you can nosh on it at the beach. For bar food, head to Ghost Isle Brewery and pair their beers with dishes designed for the occasion.

Day Trips from Chicago: Outdoor Adventures

Apple Picking

Approximate Drive Time: Varies, but there are many options within 2 hours or less.

Distance: Varies 

When fall harvest arrives, Chicago residents head straight for the orchards to stock up on the season’s best edible rubies – apples, that is, in more new and heirloom varieties than you can count. Bite into one fresh off the tree, and you’ll detest the yearlong wait until your next visit. Luckily, the versatile apple will leave you with no shortage of creations to cook up with that 20 lb. bag of fruit you bring home. Applesauce, apple butter, apple pie, apple cake, apple tart, apples in salads, apple chutney, apples with pork or chicken, apples with cheddar on a cheese plate, … you get the idea.

To start you off on this juicy adventure, consider Heinz Orchard for a more lowkey operation with no frills attached, or take the more carnivalesque route at Kuipers Family Farm, with games, farm animals, food trucks, a corn maze, and much more to occupy the whole family for a full day of activities. TimeOut’s list of apple-picking options will keep you busy for years to come. Check with the farm you plan to visit ahead of time because opening and closing dates will vary by season, depending on that year’s weather patterns. The available fruit varieties will also shift throughout the fall months as different types of apples ripen at different times.

Chicago Botanic Garden

Approximate Drive Time: 30 minutes

Distance: 25 miles

Step away from your screens, put down your phone, and get in touch with nature’s beauty at the Chicago Botanic Garden, a little north of the city and just off of the 94 freeway. Starting in April, when the spring flowers begin to bloom, the landscape will evolve with the seasons all the way through winter. Thus, you can visit throughout the year, and it will look different each time. Twenty-eight gardens plus four natural areas comprise this 385-acre outdoor living museum. Special events, such as the winter Lightscape, attract crowds, even in colder months. The Chicago Botanic Garden also offer many fascinating educational opportunities for people of all ages, so look at their calendar and class lists in case you see a subject that sparks your interest.

Morton Arboretum

Approximate Drive Time: 30 minutes

Distance: 27 miles

Another outdoor living museum that allows you to experience nature without getting dirty (unless you want to), the Morton Arboretum specializes in trees. Indeed, they describe this place as “the champion of trees,” aiming to grow, study, exhibit, and conserve our oxygen-producing friends. This all around beautiful place to explore incorporates some clever and imposing art installations made of natural materials into its landscapes (keep an eye out for giant trolls) and a stellar light show in winter that attracts nightly crowds. A maze garden, children’s play garden, tree collections with specimens from all over the world, and 16 miles of trails make this a great place to return to again and again whenever you want to explore and discover while taking in the sunshine.

Six Flags Great America, Gurnee, IL

Approximate Drive Time: 55 minutes

Distance: 46 miles

For a less natural, but more thrilling day trip, get your screams in as you drop from one height to another across the rollercoaster lined landscape at Six Flags Great America in Gurnee. Corkscrews, free falls, spinning machines, swinging contraptions, and even a few water adventures will keep your risk taking heart pounding all day. If you love theme parks with rides that break records for their fear factor, Great America is calling you. However, adventurers of all ages will enjoy their visit here because they also offer plenty of kids rides and family activities. So, no matter who joins your thrill-seeking party, the attractions here promise an exhilarating day for everyone. And, don’t leave without eating at least one funnel cake and a churro, otherwise why bother coming to an amusement park at all?

Waterfall Glen, IL

Approximate Drive Time: 30 minutes

Distance: 25 miles

So close to Chicago, and yet a world away, Waterfall Glen provides ample trails for hikers, bikers, and runners, with an opportunity to play in a small waterfall. Over 10 miles of trails make this preserved land great for observing wildlife and identifying hundreds of native plant species while improving your fitness level. You can also go horseback riding, cross-country skiing, and fishing here as well. We recommend packing a picnic and bringing it along for whichever type of waterfall adventure you choose.

Indiana Dunes National Park, IN

Approximate Drive Time: 55 minutes

Distance: 49 miles

Great for hiking, camping, and beach days, this nearby national park stretches for about 15 miles along the southern coast of Lake Michigan. Plan ahead because you do need a pass to enter the Indiana Dunes National Park, which you can purchase online or upon arrival. In September, they host an Outdoor Adventure Festival, and a wide variety of other land and water activities happen year round, so keep an eye on their calendar. Volunteer opportunities will give you the chance to become stewards of our precious natural lands, and kids can even become junior rangers. Plus, this park provides visitors with an ideal setting for geocaching, photography, birdwatching, and gardening at the historic farm, among other hobbies.

Make Chicago Your Home Base

To get to all of these wonderful day trips from Chicago, you’ll want to set up a centrally located home base in the city. To do that, simply contact us at AptAmigo, where we help thousands of people find the luxury apartment of their dreams each year. Tell us what you want in your next home, and we’ll take care of the rest.

Feeling concerned about those legendary Chicago winters? Don’t fret! Check out our guide to surviving this most frigid season.

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About Us

AptAmigo has a simple goal: to make finding an apartment easy and maybe even a little fun. With concierge-level care and an expert understanding of the local rental market, we’re more than your average apartment website. We’re perfecting done-for-you apartment searching, and we’re doing it all for free. Reach out to us today and start your VIP apartment search.