6 of the Best Day Trips from Chicago – CuddlyNest

Can’t choose from the best day trips from Chicago? We can help. Although there are plenty of fun things to do in Chicago, Illinois, from splashing around in Crown Fountain in Millennium Park to gazing at the stars in the Doane Observatory at Adler Planetarium, you may want to go for a quick day trip outside the city once in a while. However, before you embark on a train or catch a flight at Chicago O’Hare or Midway airports, make sure you have seen it all in Chicago City!

What to See in Chicago?

Quick Day Trip from Chicago to the Suburbs

There are as many people in Chicago as there are in some of Europe’s smaller countries. So in order to create some space from the hustle and bustle, explore Chicago’s suburbs. There is plenty to do in the outskirts of the city. You can start by taking the bus or metro to undiscovered neighborhoods right outside of Chicago!

Arts in Skokie and Highland Park

Feeling artsy? Just hop on the subway to Evanston or take the line 147 bus to arrive in Skokie. There is plenty to do and see, but make sure you include the Skokie North Shore Center for Performing Arts in your route. It is a massive two-theater complex that features incredible plays and shows. If you are looking to get involved in the action, you can also take classes in circus, dance, theater, art and music.

However, if Skokie is not on your way, Highland Park is packed with music lovers. One of the best times to visit is during the Ravinia Music Festival in summer. Art Center Highland Park is open to visitors year-round, so you won’t miss out no matter what time of year you visit. 

Climbing in West Loop

Are spots your thing? If climbing, yoga, or and even weights is your calling, then Brooklyn Boulders, a massive facility for sports is currently open to everyone. In keeping with the current pandemic restrictions, reservations are encouraged to keep everybody safe and healthy.  You can climb the wall whenever you want! However, you can also just walk to Union Park, or take a swim, or play tennis in their courts.

Culture Shock in Chinatown

Looking to explore new cultures? The Chinatown neighborhood in Chicago around Cermak and Wentworth Avenues is an ethnic Chinese neighborhood housing around 93,000 people of Chinese descent. Chicago is the second oldest Chinese settlement in America, with its creation in 1912. However, settlers first began arriving in the late 19th century. Today, you can dine in one of the many Chinese restaurants, shop on Wentworth Avenue, or go sightseeing in Chinatown Square which is decorated with animal sculptures to represent the Chinese Zodiac signs.

Questions we get asked a lot:

What’s a Good Day Trip from Chicago?

The best day trips from Chicago by car are to Cedarburg, Milauwkee, Rockford, Oglesby, and Madison. But you can also hop on the bus or take the train to be a responsible traveler and reduce your ecological footprint to arrive at these destinations. The best family day trips from Chicago with pets and family are to Oglesby, where you can hike with your dog, however your furry friend must remain on leash.

Where can I go by Train from Chicago?

Chicago is well connected by trains, thanks to its old-world history. You can go to Milwaukee, Indianapolis, Ann Arbor, Detroit, or Kansas City, and take your pets with you on Amtrak trains.

The 7 Best Day Trips from Chicago

The Best Day Trips from Chicago to Cedarburg

The best Day Trip from Chicago to Cedarburg by train

Getting from Chicago to Cedarburg takes around 3 hours by bus and will cost you anywhere from $27 to $58 one-way. To fully experience Cedarburg with its theaters, museums and more, visit St. Joan of Arc Chapel, Pabst Mansion, and Annunciation Greek Orthodox Church. To add to these historical and religious sites, go to Covered Bridge, which is one of the few remaining covered bridges in Wisconsin state that once had around 40 covered bridges, and dates all the way back to 1876. To have some fun with kids, and fully experience its history, explore the Ozaukee Interurban Trail from Milwaukee to Random Lake.

Day Trip from Chicago to Rockford

Day Trip to Rockford for Families 

If you are looking for day trip ideas for families, then Rockford is a good choice. Located just 100 miles away, this neighborhood is home to the Discovery Center Museum. This center offers more than 300 exhibits ranging from electricity to flights to art. Next, if you seek some family fun, then Volcano Falls features go-karts, laser tag and even miniature golf to fulfill every kid’s dream. After kart racing and maybe even NASCAR-sanctioned trucks in Rockford Speedway (the only one in Illinois!), you can eat some Italian pizza at Lino’s or Francesco’s Restaurant.

To get your nature fix and some physical activity, go to Answerson Japanese gardens which is a must in the cherry-blossom season in April. The garden is filled with beautiful flowers, towering trees, and two picturesque koi ponds accessible by lovely pathways. The place can definitely offer you the serene ending of your trip.

Hiking Day Trip to Oglesby from Chicago with Pets

Although the town of Oglesby is rather sleepy, it is home to several hiking and biking trails, and is located between Starved Rock State Park and Matthiessen State Parks. You can hike, kayak, or ride ponies, as well as travel down the rivers on rafts here.

Starved Rock State Park has been home to humans since 8000 B.C., when Hopewellian, Woodland and Mississippian Native American cultures arrived and lived here. From the 1500s to 1700s, Illinois (Native American tribe) lived here until the French arrived and claimed the land in the first half of the 17th century. The park derives its name from the American legend, according to which the allied Potawatomi and Ottawa tribes surrounded and held the ground until hapless Illinois died of starvation, hence, the name of Starved Rock  State Park was given to this national park.

While the visitor center is currently closed, you can go to Bald Eagle viewing, hiking (even with dogs when leashed) and choose trails that range from 1 mile, to 3, or 10-mile combination hikes, according to your preferred activity level. You can also go fishing or boating, and hunting in summer, or climbing and cross-country skiing with rentals operating at Matthiessen Dells Area on weekends in December through March. The opportunities for active time outdoors are endless here!

Starved Rock State park is within the bounds of Illinois reachable in 2 hours by driving, or by train and bus (also daily night bus) through Ottawa. The reserve features 18 canyons, some of which are closed during the current Coronavirus pandemic, and you must wear the mask. However, the park is currently open, and offers picnic possibilities with playgrounds for children, as well as other attractions. 

Day Trip from Chicago to Milwaukee

Milwaukee is only an hour-and-half train ride away (operating every 2 hours on weekdays), but you can also hop on the bus and arrive in Milwaukee in 2 hours. The city is the ultimate destination for those who enjoy great shops, cafes and restaurant culture. After strolling along Milwaukee RiverWalk, stop in one of many great restaurants – we recommend going to have some pancakes and mimosas at SweetDiner, or seek refuge in Milwaukee Public Market to have a seafood snack at St. paul Fish Company. 


If you like arts and culture, Milwaukee RiverWalk also hosts numerous pieces in their outdoor gallery, but for those seeking to learn about the history of the city, explanatory colorful signs are placed along the RiverWalk.


If you take kids with you, definitely visit Milwaukee County Zoo and Discovery World, and go for sweet treats, like hand-dipped chocolate, to Kehr’s Candies. Want a sweet treat for yourself as well? The Thief Wine Shop and Bar will introduce you to old-world wine traditions. You can also taste the best cheese curds in the Lakefront Brewery.

Romantic Day Trip from Chicago to Madison

Located between two lakes, Madison is full of beautiful sights, in addition to cheese and beer. The college town offers great prices for those willing to save on their foodie experiences and see it all. While at the same time not compromising on beautiful places to take your weekly Instagram post. You can rent a bicycle in B-cycle stations offering 30-minute rides, or Budget Bicycle Center from $10 for the whole day. 

When strolling around the city, make sure to include a visit to the smallest lake, the Lake Monona, to indulge in the romantic and picturesque landscape panorama. Afterwards, bring your loved one to Malt House brewery, nicknamed as a craft beer oasis and dating back to the Civil War era. You can also try the best Wisconsin cheese at Capitol Square, and shop for cheese curds in Vern’s Cheese Inc. in Chilton. Fresh and beer-battered in buttermilk/lager mix, these curds will be a true foodie delicacy. 

To go to Madison, the best and sustainable travel options are bus rides, which will take you around 3 hours, or train and bus combination (with change in Milwaukee for bus – again, you can bring your fido on Amtrak trains). You can get to Madison starting from $10. 

Tasty Foodie Day Trip to Fennville, Michigan

If cheese and beer are for those visiting Madison, then Fennville is definitely for those who value sparkly wine and cider. The best things to do in Fennville include visiting Fenn Valley vineyards with wine tasting, and Virtue Cider, Blue Star Farms to taste Michigan-grown apple farmhouse cider and indulge in hand picked blueberries. The Black Star Farms features wine tasting rooms and a distillery, so you should book the visit beforehand.

To get to Fennville, it takes 2 hours driving, or 3 to 4 hours by bus or train. Depending on transportation mode, and will cost you $62 – $82 one-way. 

Weekend Trip from Chicago to Niagara Falls

If nature is your calling, then Niagara Falls is the way to go! Although it is rather a 3 day or weekend trip from Chicago, everyone must visit Niagara Falls at least once in their lifetime. You can get to Niagara Falls by train via Buffalo, or by bus via Hamilton, or renting a car and driving for 9 hours. On the go, stop in Kalamazoo and Flint, as well as drive through London to arrive at Niagara Falls at night. You can also split the road trip in two days.

Arrive at Niagara Falls, sport a poncho and hop on a boat tour to get closer to the misty water! Boats shuttle visitors to the base of the falls and have since the 1840s. You can also save time to visit the 17th century Old Fort Niagara on the U.S. side of the falls. The forts have stood the time, and have changed hands between the French, British and American troops.

Weekend Trip to Mammoth Cave National Park with Pet

There are several options for you to bring your pet on your outdoor adventure. You can take Mercury’s Canine Cruise from $37 for adults, and $8 for dogs. Dogs can sit on your lap while you are learning about Chiago’s history. You can also take your small fido on Amtrak trains from Chicago to anywhere for $26 on trips up to seven hours, such as Cedarburg. 

If you want to get sportier and give some happy hours to your dog, then Mammoth Cave National Park allows small (up to 6 feet) leashed pets on all surface trails in the park. Mammoth Cave National Park is also providing a day-boarding for your pet (dog and cat friendly) while you are on the cave tour. However, remember to take your proof of vaccination – it is needed upon entering the kennel. 

But what’s in there for you and your kids? As it is a 7-hour drive from Chicago, you may want to split your trip into a full weekend getaway. After all, visiting the longest cave system in the world takes time. It houses the history of human development and has a rich diversity of plant and animal life, being listed under UNESCO World Heritage Site and International Biosphere Reserve lists. However, make sure you plan your visit ahead of time, as during the Covid-19 pandemic, Green River Ferry is closed, river access and ticket availability is limited to ensure the cave’s capacity is not overrun. 

That’s it for day trips. Here are some more questions we get asked a lot:

Can I do a day trip from Chicago to Detroit?

To go from Chicago to Detroit, you can take a 5-hour train from $35 one-way and take your small dog with you. To go back and forth, it will take 10 hours, so we encourage you to book a place to stay in Detroit and make it a 2-day or weekend trip instead.

Where to go for a one-day trip from Chicago center?

Good day trips from Chicago center are to Madison, Fennville, or Milwaukee. Chicago center has a direct trainline (we encourage the most sustainable way of transportation) to Holland and Fennville, as well as Milwaukee, and after changing in Milwaukee to bus, you can go to Madison. 

What city is 3 hours away from Chicago?

Holland, Kalamazoo, South Bend, Lafayette, Janesville, Milwaukee and Springfield are good options for a one day trip from Chicago, as they are under 3 hours by train, bus or car ride.

Now that you have discovered the top day trips from Chicago, it’s time to plan your stay. Find the best hotels and vacation rentals on CuddlyNest to stay at while you explore Illinois’ most adventurous sights.

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