Last Updated on
Chicago is known as the Windy City, and it’s a bracing metropolis overlooking the windswept shores of Lake Michigan in the north of the USA. While it’s a beautiful city to visit, and a place brimming with history and culture, the freezing weather might soon have you looking for a new destination to escape to!
Luckily, Chicago makes the perfect base from which to explore the surrounding region, with the city located perfectly on the borders between the states of Illinois, Wisconsin, Indiana and Michigan. There’s a lot going on in this part of the United States, and there are plenty of great opportunities to get out of the Windy City.
There are a lot of great excursions that you can make from Chicago, with cities, national parks and spectacular wilderness all within easy reach of the city. And to help you decide on the best spots to hit up during your stay in the great state of Illinois here’s our guide to the best of the day trips, handpicked by some of the best travel writers in the business.
Here we go! Here are the 16 best day trips from Chicago!
Table of Contents
Milwaukee is found on the western shores of Lake Michigan, and for travellers, it’s just a two-hour train ride from central Chicago!
This is one of the best day trips from Chicago by train, not just because of the frequent departures and returns or the relatively short journey time, but because Milwaukee is home to some of the best breweries in the northern states.
In the past, the large number of breweries even led to the city being named the “Beer Capital of the World” in some beer circles! Today, the legacy is proudly continued by locals, and you can tour through some of the best craft breweries in the USA on your day trip here.
When you arrive in Milwaukee, you can join a sightseeing bus tour to see the highlights of the city. Stop off at the Harley Davidson Museum to see where the infamous motorcycle brand began life over a century ago.
Call in at the Milwaukee Art Museum for a taste of the local culture, before strolling along the marvellously beautiful Riverside Walk. Round off the day with a visit to the Lakefront Brewery for supreme scenery and to dabble in the local brews before catching the train back to Chicago again.
Editor’s Note: One of the best ways to get to know Chicago is through its museums.
Springfield is a small city to the south west of Chicago, and for lovers of all things history, it makes for a wonderful day trip from Chicago.
Springfield – no, it’s not the Simpsons’ hometown! – is three hours away from Chicago on the Lincoln Service, named for the famous President of the United States of America. While Chicago might be the largest city in Illinois, Springfield is actually the state capital, home to the government and very centrally located.
Abraham Lincoln lived in Springfield for several decades when he worked for the state and before he was elected as President of the entire country.
The state capital is a great place to learn more about local history – or perhaps, all things Abraham Lincoln! – as you can tour through Lincoln’s old home, visit the Lincoln Monument and visit the Abraham Lincoln Presidential Library and Museum, which holds a huge collection of documents and papers detailing the man’s life and actions.
After this, you can call in to pay your respects at Lincoln’s Tomb, and once you’re all Lincoln-ed out, then you can visit the Springfield Lake or one of the many local parks to see a different, non-Lincoln side to the city.
Insider Guide! These are the absolute BEST times of the year to visit Chicago!
The somewhat intriguingly named Wolverine Line train runs from Chicago, along the edge of Lake Milwaukee and out east to the equally intriguingly named city of Kalamazoo in 2 hours.
Kalamazoo is famous for its unique outdoor shopping mall, which was the first fully pedestrianised shopping area in the entire country. It’s been revitalised in recent years and continues to be a big draw for visitors to the city, who can shop and enjoy a piece of national history at the same time!
There’s more to Kalamazoo though than just an old shopping mall, so don’t worry if shopping isn’t your thing! Check out the Kalamazoo Valley Museum if you want to learn about the real history of the area, including prehistoric artefacts and archaeological finds dating back thousands of years. There’s even a planetarium if you want to enjoy a spot of stargazing.
If cars are your thing, then call in at the Gilmore Car Museum, to see an absolutely enormous private collection of vintage cars, collected over decades. It’s the largest of its kind in the country and a real highlight of visiting Kalamazoo.
Closer to Chicago, on the southern shore of Lake Michigan, is the city of New Buffalo. It’s a short, one and a half hour train ride away across the state border, again on the Wolverine Line.
The city is small, with a population of just under 2000, but that makes it perfect if you are hungering for a small town escape from the metropolis of Chicago. New Buffalo is found along the lake shore, and it’s a favourite spot for hanging out and enjoying Lake Michigan.
The City Beach is the best spot to head to first, for epic views and to relax in the outdoors. It’s a sandy beach and in summer, you could easily imagine you were on the coast, and not in the state of Michigan!
New Buffalo has plenty of recreational facilities too, and if you are looking to pursue a few more adventurous activities, then you can hire kayaks, canoes or paddleboards to take out onto the water and to experience the beautiful nature while you get a little bit of exercise too.
I’m sure you know a bit about Chicago, but we have a few history facts you might not have heard yet.
From central Chicago, jump on a train and you can soon be whisked away from the confines of the city and into the wilderness of the Indiana Dunes National Park. Hop off at the Dune Park Station and a short walk will bring you into the depths of the nature preserve that’s found along the southern shore of Lake Michigan.
The national park encompasses several areas of natural beauty, including sandy beaches and rolling dunes. It’s these dunes that the park aims to preserve. As well as these beaches though, the area is renowned for its supreme hiking opportunities, while in summer, you can brave the chilly water of the lake for a swim.
While you can experience the best of the Indiana Dunes in a day trip from Chicago by train, there’s actually a designated and well-provisioned campsite within the park, so if you fancy turning this into an overnight, or multi-day getaway, then the great outdoors is waiting for you.
The city of South Bend is a two-hour train ride to the east of Chicago, and it makes for a great day trip if you are looking for an insight into local life in the Midwest. South Bend is found in northern Indiana, in a beautiful location along a bend in the St Joseph River.
The river forms the centrepiece of the city and in the evenings, is host to epic light shows that are played out vibrantly along the banks to light up the night sky. As well as the River Lights display, there’s much to do in South Bend on a day trip from Chicago.
You can visit the local chocolate museum to sample some Midwest delights after touring through their premises to learn about the production process and the history of chocolate in South Bend.
There’s the National Studebaker Museum to explore, where you can see some of the American car manufacturers classic vehicles on display, including their 19th-century carriages. You can even see the carriage that Abraham Lincoln took to the play where he was assassinated. Morbid, but fascinating.
Couples won’t want to miss out on the beautiful chance to escape the city and to enjoy the serene skyline from afar, as they travel out onto Lake Michigan for a romantic dinner date aboard a cruise ship.
Take your date on a trip to remember, as you cruise along the calm waters of the lake and enjoy splendid views of Chicago in the distance. You can travel out for lunch or for dinner, or perhaps even arrange a full day excursion too if you really want to impress.
Enjoy a gourmet meal aboard a modern vessel, alongside premium drinks and cocktails, while you’re entertained by music, and perhaps even fireworks once the sun has set!
Michigan may at first glance seem to be far too northern for the production of quality grapes and wines, but actually, there’s a little known wine valley in the south west of the state that’s been growing and producing excellent wine for decades.
There are several wineries in the area, and they are all just a 90-minute drive from downtown Chicago. You’re best joining a tour for this day trip, allowing you to travel to the best wineries in Michigan and allowing you to drink as much as you want!
There are several wineries included on most tours from Chicago, to give you a good feel for the wide variety of wines that are created here. You’ll enjoy sampling different vintages while learning about the unique grapes that are grown here despite the colder weather.
It’s a great chance to see the beautiful countryside of Michigan and to get a little tipsy on some of the best wines in the northern United States.
Editor’s Recommendation – You should definitely check out our guide on the things to do in Chicago, Illinois!
Lake Geneva is one of the best places to visit if you are looking for a romantic day trip from Chicago for couples. The lake is a two-hour drive away from the city, over the state border in Wisconsin.
While it can’t compete with Lake Michigan for size, Lake Geneva is one of the most aesthetic spots in the region. It’s perfect for romantic walks through the forest or strolls along the calm lakefront. Lake Geneva is a resort destination and it’s popular with day trippers looking to escape Chicago, to find some peace, quiet and beautiful scenery.
To cater to the visitors, there are some fine restaurants, cafes and bars where you can lunch at, before returning in the afternoon to the noise and chaos of the city!
You can cruise across Lake Geneva, enjoy hiking or walking, or take to the water in kayaks or canoes if you are looking for a more active adventure.
In the northern suburbs of Chicago, Glencoe hosts one of the most beautiful and colourful botanic gardens in the region. The Chicago Botanic Gardens are a masterpiece of design and landscaping, and they are just a one hour drive from downtown.
This is the perfect day trip for couples, and you can spend hours simply strolling through the pleasant climes of the gardens, enjoying the vibrant colours and colourful scenes arrayed out before you.
There’s a cafe serving wonderful food and refreshments, you can ride a tram through the gardens, or just walk, and you can enjoy a picture perfect escape from Chicago, while never actually straying too far from the city centre.
Surprise your partner with this grand romantic gesture, and take them on a day trip to New York! The city might be over 800 miles away on the east coast, but rather than spending the entire day driving, you can be there in just two hours if you fly.
It’s an extravagant day trip to make, but one which is perfect for romantic couples looking for a big expression of grandeur. After landing in the morning in New York, you can explore the city’s most iconic sights using the hop on hop off bus.
Visit Central Park and stroll through the leafy green surroundings of one of the largest outdoor, urban areas in the world. Take the elevator to the viewing deck of the Empire State Building for unparalleled views over the city. Ride the ferry across to Ellis Island and back, take the subway to classic attractions and enjoy the excitement of Times Square.
It’s a long day, but it’s one of the most unique day trips that you can make from Chicago.
Heading to Chicago too? Save some money with our local guide to Chicago’s best hotels!
Illinois Beach State Park is just an hour and a half north of Chicago and it’s a great place to take the whole family for the day. Here you can find over 6 miles of pristine, sandy beaches stretching along Lake Michigan.
You can sit back on the sand, building sand castles with the kids, or jump in the water in summer to cool off. There are plenty of recreational activities for the whole family too, and you can hire kayaks and canoes, stroll along the lake or bring your bicycles to explore even more the area.
Starved Rock State Park is a two-hour drive inland, to the west of Chicago on the Illinois River. This spectacular state park is a veritable natural playground for kids, with canyons, waterfalls, creeks and more just waiting to be explored by the adventurous!
This is a real masterpiece of natural attractions, with towering waterfalls crashing down into canyons, and bald eagles soaring overhead. The kids will love the activities on offer here, from hiking to swimming, and they can learn more about the natural world by joining the Junior Rangers programme here too.
It’s a bit of a drive away from Chicago, but it’s worth taking the kids on a road trip into the heart of Wisconsin to see one of the most unusual, yet strangely electrifying tourist attraction.
The House on the Rock is a strange array of different rooms and buildings, built atop a tall, prominent rock in the countryside. It’s a maze, and the kids will love exploring the fascinating rooms and collections found in the rooms.
There are dinosaurs, carousels, Santas and more weird and wonderful creations waiting to be discovered at the House on the Rock. The most impressive creation is the huge Infinity Room, which extends for a large distance, entirely unsupported, from the top of the rock. Enter if you dare!
Editor’s Note – Have you seen our guide to the most underrated and COOLEST neighborhoods in Chicago?
Wisconsin Dells make for the perfect day trip from Chicago with kids because this is waterpark central! The small town’s tagline is the unashamed ‘Wisconsin Dells, Waterpark Capital of the World’ because here you can find indoor and outdoor waterparks all over the place.
That means that you can visit the Wisconsin Dells any time of the year and still enjoy a trip to the waterpark, while in summer you can enjoy the great outdoors too, before jumping into the waterparks to cool down in style!
As well as the ubiquitous waterparks, Wisconsin Dells is also home to a more traditional theme park, complete with roller coasters and other rides that will keep all the family thrilled. The parents can take to the golf course too, if they need a break, while if you fancy making this into more than just a day trip from Chicago, there are plenty of resorts and accommodation options here too.
An hour up the road from central Chicago is Six Flags Great America, a terrific theme park with plenty of fun to be had for the whole family. This is the most popular theme park in the Midwest and one of the most popular in the entire country, meaning that the kids are guaranteed to love it!
There are hundreds of different rides spread across different themed areas, each with their own unique stories, designs and attractions. It’s a great day out from Chicago!
Whatever type of trip you’re looking for when you are visiting Chicago, the city is surrounded by a huge array of opportunities, be it for romantic getaways or family excursions.
The local rail network gives you the chance to explore further afield and still return to Chicago in the same day, while the exceptional national parks and lakeside retreats will have you wanting to stay much, much longer.
Chicago is a great place to day trip, and there are endless trips to make. If you think that we’ve missed any of the best day trips from Chicago, then let us know in the comments!
*** Some of the links on Hotel Jules are affiliate links, which means if you do make a purchase, we may make a small commission (at no extra cost to you.) Thank you for using our links! Your support keeps the site going***
Emma Johnson lives to travel! Born in Washington D.C., Emma is a hotel connoisseur and a staff writer at Hotel Jules. An army brat, Emma got the travel bug early and has never been able to stop. Now, she has proudly visited 70+ countries and plans to visit every country in the world! Passionate about her ukelele (obviously) and her family, Emma eventually wants to retire in Thailand and write a book about all of her travel experiences.