Day Trips from Chicago: Trails, Parks & Landmarks

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If you’re currently in the Windy City but are out of fun things to do since you’ve already seen and done everything, the best solution is to start taking day trips from Chicago because Illinois has so much beauty to offer. It would be a shame to miss it all.

Discover hidden gems, travel far out for a memorable experience, or visit places that make you feel like you’ve left the state. Lake Michigan’s scenic shores promise tranquility, surrounding state parks allow you to bond with nature, and nearby towns have no shortage of unmissable sightseeing.

So, what are you waiting for? Grab your car keys (or train tickets) and hop on the road to uncover new places and unlock memorable adventures!

P.S. You might also like these free things to do in Chicago.

1. Escape to the Scenic Shores of Lake Michigan

Lake Michigan should be one of the first destinations that come to mind when planning day trips from Chicago. It’s one of North America’s five Great Lakes, offering a tranquil beachy experience to cool down and unwind.

Chicago boasts 26 miles (41.8 kilometers) of the Lake Michigan shoreline that can keep you busy all day. Lake Michigan’s southern shore is home to one of the most popular beaches in Chi-town: North Avenue Beach.

This little haven for beach bums is a vibe, with volleyball nets, jet-skis, paddle boards, DJs, and margaritas keeping things buzzing.

Other fantastic beaches include Oak Street Beach and Montrose Beach. Lake Michigan is best visited in summer, and you don’t have to travel far to enjoy the paradisiacal lakefront. You can spend time at Millennium Park and Grant Park, Shedd Aquarium, and the Field Museum or hop on a boat cruise at the Navy Pier. 

Note: While it is generally safe to swim in Lake Michigan, it does have dangerous rip currents and harmful bacteria. In that case, do your research on beach safety before swimming.   

2. Wander Off to the Windmill Island Gardens

The magical Windmill Island Gardens is the type of place that one imagines when reading a fairytale set in the Netherlands. This beautiful seasonal park enchants you with vibrant tulip gardens, a carousel, and a 250-year-old windmill.

It’s genuinely post-card-ready, so you simply must take the day to drive out to Holland, Michigan, where it’s located. You’ll have to pay an admission fee of $12 to enter, but this authentic Dutch windmill is worth every penny. And guess what – it’s still turning and grinding wheat into flour today.

The drive to the gardens will take roughly two hours and 20 minutes out of your day. You can visit during the Peak Bloom Week (23-29 July) for a stunning display of color. If big crowds aren’t for you, going one week before or after this festival would be better. 

Note: This group-friendly attraction is only open annually from mid-April through early October.

3. Explore Starved Rock State Park

Gateway to the Illinois River and home to 18 striking canyons, this state park draws many travelers for a reason. You’ll see dramatic canyons with moss-covered vertical walls, sparkling waterfalls, and tree-covered sandstone bluffs.

Its wilderness landscape and sightseeing opportunities have made this park a well-known spot for hikers, photographers, bird-watchers, and horse riders.

Starved Rock State Park is also an excellent opportunity for photography, fishing, kayaking, and boating. This quick day trip is ideal for nature lovers and outdoor enthusiasts who need a break from the city.

The park is free to enter and open every day of the year from 7:00 am to sunset. The most rewarding time to visit this park is in the fall when it transforms into an array of bright colors – peak foliage occurs around mid-October.

You can drive to the park from Chicago in under two hours, and public transport is available to travel this route, including trains and taxis.

4. Admire the Anderson Japanese Gardens

If you happen to be in Chicago between May 1st through October 31st, then you don’t want to miss this splendid day trip to the Japanese Gardens. But why should you travel all the way to Rockford just to see a garden?

The Anderson Japanese Garden is not just any old garden. It’s a rare opportunity to see a traditional Japanese garden crafted by visionary John R. Anderson and landscape architect Hoichi Kurisu.

Its construction started in 1978 and continues to charm visitors with gentle streams, koi-filled ponds, cherry blossoms, gushing waterfalls, and winding paths with picturesque bridges.  

You can take your time walking through this whimsical garden to absorb the peace and calm. You’ll reach the gardens in about an hour and a half by car and typically spend one to two hours wandering through it.

Driving there yourself will be the quickest, but there are buses, trains, and taxis available from Chicago O’Hare Airport in about three hours.

5. See the Iconic Buildings Designed By Frank Lloyd Wright at Oak Park Village

Oak Park is a charming village in Cook County and less than a 15-minute drive from Chicago. This short distance makes it the perfect quick day trip. The village is famous for the world’s largest collection of buildings designed by celebrated architect Frank Lloyd Wright.

Wright pioneered organic architecture with his signature “Prairie style,” putting this small village on the map. Interestingly, Oak Park is also the birthplace of well-known American novelist Ernest Hemingway. So, the place must have a bit of “genius” luck, giving you all the more reason to visit.

While here, you can simply walk about and take in the beauty of Wright’s creative imagination. These houses are now considered a national historic landmark, including the Walter Gale House, Arthur Heurtley House, and the Nathan G. Moore House.

And, of course, one shouldn’t forget about popping in at the home and studio of Frank Lloyd Wright.

When you’re done admiring the houses, you can explore more of Oak Park. See the Ernest Hemingway Birthplace Museum, stroll through the Oak Park Conservatory botanical garden, or try local restaurants and café. 

Visit Oak Park during the fall or summer for pleasant weather to roam outside. Traveling there via public transport is affordable and convenient if you’re in Chicago without wheels. Board a 15-minute train ride or grab a taxi cab for a 10-minute drive – it’s that easy.

6.  Hit Some Hiking Trails at Indiana Dunes National Park

If you’re an avid hiker, then a day trip to Indiana Dunes National Park is just what the doctor ordered. This one is highly recommended of all the state parks in the surrounding region, thanks to over 50 miles of breathtaking trails.

These pathways meander through a rich mosaic of habitats, from sunny prairies and lush wetlands to dunes and serene woodlands.

The absolute best hike one must pick up in this park is called the moderate Cowles Bog Trail. This one-and-a-half-hour trail is dotted with wildflowers and blessed with gorgeous vistas, including ocean views. You can stop at a secluded beach for some quiet time and comb through wetlands, dunes, and forests. 

A quick and easy hike is the West Beach-Dune Succession Trail, which can be completed in roughly 20 minutes. Most of the hikes here are moderate to easy and completed within two hours, so it might not be ideal for those who are suckers for a challenging route.

The general areas of the park are open year-round, and the daily operating hours are from 6:00 am to 11:00 pm. This gives you enough time to make the 50-minute drive from Chicago, stop at a local eatery for breakfast, and complete your hike leisurely.

Pro Tip: Prepare for your hiking day trip in Indiana Dunes National Park. In the warmer months, wear sun protection, carry enough water, and watch out for wildlife. In the colder months, ensure waterproof clothing, gear, and snowshoes for slippery conditions.

7. Break Away to Lake Geneva

Lake Geneva is a stunning resort city on Geneva Lake, Wisconsin. Dripping in opulence, this city is peppered with Gilded Age mansions, scenic beaches, and verdant trails. You can simply admire the mansions from Geneva Lake Shore Path or indulge in boating and other water sports during summer.

This quaint town will remind you of Europe. Hence, it’s named after Geneva, an awe-inspiring city in Switzerland. You’ll see hints of this in the Queen Anne-style houses and the medieval village of Yvoire, located on the French shore. The palace-like buildings reflecting on the lake below make for an unmissable scenery.

Lake Geneva also offers some exciting activities you can do throughout the day. You can have a lovely picnic at Big Foot Beach State Park or zipline at Lake Geneva Ziplines & Adventures. The Lake Geneva Cruise Line offers relaxing boat tours while you can learn more about the local history at the Geneva Lake Museum.

Then, there’s Topsy Turvy Brewery, Safari Lake Geneva, and the Tristan Crist Magic Theater if you’re keen on mind-boggling illusions. Lake Geneva starts to get quiet as fall sets in, and ski season kicks in if you are hoping for a calm retreat.

Otherwise, June is the best time to visit Lake Geneva as it’s not too uncomfortably hot but warm enough for outdoor activities.

The drive to Lake Geneva will take about one hour and 20 minutes by car. You can also opt for a two-hour train or taxi ride from Chicago Union Station.  

8. Take a Day Trip to a Wisconsin Resort City

Wisconsin sits roughly three hours from Chicago if you’re traveling by car. This makes it an obvious destination to escape to. Visiting a Wisconsin resort city is one of the best things you could do for a day trip. Why?

Resort cities are an all-in-one entertainment package, fun activities, dining, and pampering. Wisconsin Dells, a town in southern Wisconsin, comes to mind first.

Here, you’ll have a pick of waterparks, luxurious resorts, theme parks and entertainment centers. This trip would be well-suited for families as it’s the “The Waterpark Capital of the World®.”

The Kalahari Resorts in Wisconsin Dells is an African-themed resort home to the largest indoor waterpark in Wisconsin, featuring a wildlife park, spa facilities, and epic water slides.

Then, there’s America’s largest outdoor water park, Noah’s Ark, and the country’s largest indoor/outdoor waterpark, the Wilderness Resort, both in this resort city.

So, if waterslides, thrilling rides, theme parks, and (let’s not be shy) noisy kiddos are your thing, don’t skip this fun day trip from Chicago. Visit this Wisconsin resort city in summer for the best weather, and while it’s better to travel with your vehicle, there are train rides that’ll get you there in about three hours.       

9. Visit Grand Rapids for the Day

Home of the infamous wet burrito, Grand Rapids is a Michigan city and your next getaway from Chicago. Sitting along the east of Lake Michigan, this city is known for its many breweries dotted all over.

Naturally, the first thing you’ll want to do when landing here is to visit one of the breweries. Grand Rapids is known for award-winning brews and the tantalizing dishes that can come with them.

Some of the best places to indulge in this stellar combo are Brass Ring Brewing, Brewery Vivant, Founders Brewing Co., and City Built Brewing Co., among a plethora of excellent options.  

After craft beers and dining, you can make your way to various attractions in the city. You’re spoilt for choice from the Frederik Meijer Gardens & Sculpture Park to the Grand Rapids Art Museum and the Fulton Street Market. Why not try something quirky with this eerie ghost tour through the city?

Traveling to Grand Rapids may take up to three hours by car, which is way better than the four to five-hour trip via train or bus from Chicago Union Station.

Fun fact: Grand Rapids is also a world leader in producing office furniture – so the next time you’re in an office, you can thank this city for the desks and chairs.

The Best Day Trips from Chicago Wrapped Up

And that’s a wrap! There are still many more day trips not even mentioned: the Mississippi River, Milwaukee Art Museum, and South Bend. So, that shows you just how plentiful your options are outside the Chicago city limits.

That said, the above-day trips will not disappoint as each offers a unique experience filled with sights, activities, and attractions. The only thing left is deciding which ones are worth your time.

Read Next: Best things to do in northern Michigan.