15 Best Day Trips From Chicago You’ll Want To Take ASAP

Looking for the best day trips from Chicago that are actually worth the drive?

I’ve rounded up the best Chicago day trips for every type of traveller, including quick nature escapes, romantic getaways, foodie towns, and easy weekend adventures.

While there is so much to do in Chicago, you might be surprised at what lies outside of the main city.

Best Day Trips From Chicago By Drive Time

Best Day Trips From Chicago Under 1 Hour

• Oak Park, Illinois
• Highwood, Illinois
• Kankakee, Illinois

Best Day Trips From Chicago Under 2 Hours

• Lake Geneva, Wisconsin
• Milwaukee, Wisconsin
• Indiana Dunes State Park, Indiana
• Oglesby, Illinois (Starved Rock Area)
• Michigan City, Indiana
• Rockford, Illinois

Best Weekend Trips From Chicago

• Monroe, Wisconsin
• Holland, Michigan
• Grand Rapids, Michigan
• Madison, Wisconsin
• New Glarus, Wisconsin

15 Best Day Trips From Chicago You’ll Want To Take ASAP

Lake Geneva Is A Classic Chicago Weekend Escape

Lake Geneva is a Wisconsin town about an hour and a half outside of Chicago.

Lake Geneva is a beautiful small town that thrives because of the large Lake Geneva, and it’s a budget-friendly day trip option.

There are so many things to do in Lake Geneva all year long that include lake activities.

You’ll also find a charming town full of unique boutiques, restaurants,

and even outdoor activities like hiking and snow sports in the winter.

In early February, the town holds a Winter Fest featuring the only snow sculpting championship in the United States.

Visitors experience massive snow sculptures, food from local restaurants – and it’s free to attend!

In the summer, enjoy boating, swimming, and kayaking on Lake Geneva before having a meal at one of the amazing local restaurants in Lake Geneva.

Indiana Dunes State Park Is One Of The Best Nature Day Trips From Chicago

Just under an hour outside of Chicago, the Indiana Dunes National Park is one of the coolest national parks in the Midwest.

The Indiana Dunes National Park is on 15 miles of beach on Lake Michigan’s South shore.

It is a nature lover’s dream with over 15,000 acres of preserved land full of unique hiking trails, wetlands, prairies, woodlands, and beaches.

From Memorial Day to Labor Day, there is a $6 entrance fee to enter the park. During the ‘off-season,’ though, it’s free to enter.

It’s a beautiful spot, and it is definitely one of the day trips from Chicago that is worth the effort.

Milwaukee Is One Of The Easiest City Day Trips From Chicago

If you are looking to explore a city, but you want a break from Chicago,

I suggest driving the hour and a half to Wisconsin’s largest city, Milwaukee.

Because Milwaukee is Wisconsin’s biggest city, it is full of unique things to do, making it one of the best day trips from Chicago!

Take a stroll down the streets and admire the many murals on the sides of buildings.

Or go window shopping in one of the many boutique stores.

Check out a play or musical, take a sightseeing tour, or explore one of the amazing restaurants in Milwaukee.

If you’re a sports fan, you may want to check out one of Milwaukee’s home teams.

Cedarburg Is One Of The Cutest Small Town Day Trips From Chicago

In just under 2 hours, you can find yourself in the charming small town in Wisconsin called Cedarburg.

Cedarburg is an excellent day trip from Chicago for those looking for small-town charm, but with plenty of activities.

There is a Candy Kitchen, an Amish Craftsmen Guild, stores full of items made by local artisans, and even a shop where you can search for unique gemstones.

There is a local art museum, a local history museum, a woolen mill and textile museum, and even a museum depicting early life in Cedarburg.

No matter your interests, Cedarburg is guaranteed to have something fun for you to do, and you’ll find it was worth the drive.

Day Trips from Chicago: Essentials Packing List

Here are my tips for packing lightly. using a carry-on when traveling. And WHY it is almost a necessity!

This unisex RFID-blocking concealed travel pouch is lightweight and comes in several colors.

These RFID sleeves are another solution.

This Anker high-speed phone charging battery is the exact one I carry on all my trips.

Don’t forget Apple AirTags to track your luggage. (Whether you fly or drive.)

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday.

It is made of lightweight aluminum and is so easy to use.

I never leave home on a trip without a non-disposable water bottle. 

Then this collapsible silicone foldable water bottle would work well for you as well.

This foldable water-resistant backpack would be great for a daily go-pack.

These quick-dry slip-on Aqua shoes will be useful at pools or beaches you happen to visit along the way.

These men’s quick-dry trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in many lens colors and frame designs and are extremely affordable, too.

If you like aviator-style sunglasses, these polarized aviators may interest you.

As an Amazon Affiliate, I earn from your qualifying purchases.

Rockford Is An Underrated Illinois Day Trip

If you drive for about an hour and a half West of Chicago, you’ll find yourself in Rockford, Illinois.

Rockford is also bursting with things to do.

Music lovers will enjoy checking out one of the many spots that hometown band Cheap Trick helped make famous.

Stop by the Burpee Museum of Natural History or the Discovery Center Museum.

Consistently rated as one of the best Japanese Gardens in North America, visit the Anderson Japanese Garden.

Grand Rapids Is Perfect For Art, Beer, And Weekend Fun

Grand Rapids is known as Beer City USA.

For those who want to take full advantage of all Beer City USA has to offer, you’ll want to download the Brewsader App.

It gives you a full map of all the breweries in Grand Rapids,

and after you check in at 8 of them, you’ll earn a fun Brewsader shirt to commemorate your trip.

If beer isn’t your thing, not to worry.

There are still some absolutely amazing and unique restaurants in Grand Rapids that you can check out.

Or you can stop into one of the city’s popular art galleries.

There really are so many cool things to do in Grand Rapids.

Oak Park Is Perfect For Architecture And History Lovers

Oak Park, Illinois, is the shortest distance you’ll have to travel for a day trip on this list as it’s just under 20 minutes outside of Chicago.

Frank Lloyd Wright called Oak Park home and left his mark on many of the city’s most popular homes and buildings.

Oak Park was also home to another famous architect, George W. Maher,

who also designed many of the city’s most prominent homes and buildings.

Ernest Hemingway was also born in Oak Park, and you can visit his childhood home, which is now a Hemingway Museum.

Because of Oak Park’s proximity to Chicago, many gangsters in the early 20th century called the area home, and you can now take a Gangster tour.

Michigan City Is A Relaxed Lake Michigan Escape From Chicago

Michigan City, Indiana, is about an hour away from Chicago, and you’ll spend the trip driving along Lake Michigan.

In Michigan City, you’ll want to explore the Old Lighthouse Museum

and even take a tour of the Michigan City Lighthouse and Pier.

Stroll along the beach or maybe head over to the Washington Park Zoo, full of interesting architecture and animals.

Travelers also enjoy touring the Barker Mansion and sipping on local wines at some of the best wineries in Indiana

Monroe, Wisconsin, Is A Charming Small Town Escape

Monroe, Wisconsin, is the Swiss Cheese Capital of the USA, and just over 2 hours away from Chicago.

Monroe is a cute small town that takes cheese very seriously.

The city has thrived for over 100 years because of its cheese industry.

You can pair some locally made cheeses with local beers or explore the numerous cheese shops.

Or watch a movie at the local drive-in theater while munching on cheese curds.

The small town even holds a yearly Cheese Days Festival where you can sample all of the local cheeses while sipping a cold local beer.

Monroe is perfect for your next day trip from Chicago when you’ve got a serious craving for all things cheese.

This cool town is one of the best places to visit in Wisconsin.

Kankakee Is A Quiet And Easy Escape From Chicago

Kankakee, Illinois, is a cute town in Illinois just over an hour south of Chicago.

Favorite things to do in Kankakee are taking a tour of the B. Harley Bradley House,

a famous house designed by Frank Lloyd Wright.

Kankakee is also amazing for those looking for a little outdoor adventure.

You can enjoy some of the best hiking in Illinois, along with canoeing, kayaking, and even scuba diving in the Haigh Quarry.

Kankakee is one of the best day trips from Chicago, Illinois, if you’re looking for fresh air, beautiful nature, and plenty of small-town charm.

New Glarus Feels Like A Tiny Slice Of Switzerland In Wisconsin

America’s Little Switzerland is in New Glarus, Wisconsin, just 2.5 hours from Chicago.

New Glarus is a small town that loves beer, cheese, and festivals. In the warmer months, they may have 3-4 festivals a month.

New Glarus is also known for having a selection of brews that you can only buy in Wisconsin, and some of them you can only buy in New Glarus.

If you are a beer connoisseur, you’ll love checking out one of the local beer gardens.

Foodies will love checking out one of the many restaurants that serve up Swiss and Swiss-inspired fare.

New Glarus is a cute romantic getaway in Wisconsin!

Holland, Michigan, Feels Like A European Escape In The Midwest

Holland Michigan is a little over 2 hours away from Chicago and is named after the home country of its original settlers.

Holland is bursting with Dutch charm.

Spring is host to the Tulip Time Festival, where you will get to see a riot of colorful tulips with a windmill that is straight from Holland.

Even if you can’t make it to the Tulip Time Festival, you’ll love exploring this cozy small town.

Holland is also home to one of the coolest lighthouses in Michigan, the Big Red Lighthouse.

Holland is a small town in Michigan, full of charm that is definitely worth the effort to visit, any time of year.

Starved Rock Near Oglesby Is One Of The Most Scenic Road Trips From Chicago

Oglesby is perfect for day trippers looking for a break from the city as it is home to two beautiful State Parks.

If you’re looking for some outdoor adventure and clear air, then you’ll find that this is one day trip that is worth the effort.

At Starved Rock State Park, you’ll find trails that lead you along the Illinois River and into steep sandstone canyons.

It’s accessible for all skill levels, and you get to experience some beautiful views.

The other state park near Oglesby is Matthiessen State Park.

The entrance is just a few miles south of Starved Rock State Park.

Matthiessen State Park has similar views, but it is often far less crowded.

It is a great choice to experience fall in Illinois.

You’ll still be able to hike beautiful trails, see gorgeous Illinois waterfalls, and enjoy nature, but you’ll be far less crowded.

If you have plenty of time on one of your day trips from Chicago, Illinois, you should definitely check out both state parks.

Highwood Is One Of The Best Foodie Day Trips From Chicago

Highwood Illinois, is another small town that goes big when it comes to festivals.

Just 35 minutes North of Chicago, this charming small town is the perfect day trip from Chicago Illinois for festival lovers

There’s almost a festival every month, and they all have different themes.

For foodies, there is a Taco Festival, a Bloody Mary Festival, and a Garlic Festival.

One of Highwood’s most iconic festivals though, is probably The Great Highwood Pumpkin Festival every October.

It is one of the coolest things to do in Illinois.

The Festival benefits the Make-A-Wish Foundation and attendees get to check out rows and rows of carved pumpkins.

Attendees of Pumpkin Fest can even bring their own pumpkins and carve them before adding them to the walls of carved pumpkins.

Madison, Wisconsin, Has Small City Charm And Beautiful Lakes

In just over two hours, you can find yourself in Madison, Wisconsin.

If you’re looking for a fun Chicago day trip in the summer, Madison is perfect for you.

With five lakes spanning over 15,000 acres, there are so many things to do in Madison.

There are water sports, festivals, waterfront dining, and so much more.

There are dinner theaters, breweries, delicious restaurants, and unique boutiques.

Put treating yourself at some of the restaurants in Madison on your list!

You’ll find that Madison, Wisconsin, is one of the most entertaining day trips from Chicago that is definitely worth the effort.