11 Unforgettable Day Trips from Chicago

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Chicago is a wonderful city in the USA worth visiting because of the food scene, nightlife, and architecture. Chicago has so many museums and neighborhoods to explore. Once you’re done touring the city, don’t miss the opportunity to take some day trips from Chicago!

Sometimes the busyness of the city can be overwhelming both for residents and travelers. Taking a day trip (or three!) allows you to breathe some fresh air and see more of the state of Illinois. 

By adding a few extra days to your itinerary, you can spend your time taking a few Chicago day trips. You can also easily visit nearby states like Michigan and Wisconsin since Chicago borders them. 

Here are the top ten day trips from Chicago and what you can expect on each of them.

bright red chicago sign, downtown chicago

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Visiting Chicago 

Heading to Illinois? Chicago is usually the first stop for most travelers to the state. A weekend in Chicago is enough to see all the best sites, but you can easily spend a few weeks or more. 

After a few days of sightseeing and touring around Chicago, here are the best places to visit near Chicago and what to do in each place:

Click the link to go directly to the section below. Or scroll down to read them all!

chicago skyline, park surrounding a highway, tall skyscrapers in the distance

1. Cycle Around Lake Geneva 

Lake Geneva is one of the best day trips to take in the warmer months. It’s a small city on the shore of Geneva, Lake in Wisconsin. The city is a resort town with many hotels, shops, and tourists. 

The Lake Geneva Shore Path is the main attraction. It’s 21 miles long and is perfect for biking and walking. Lake Geneva also offers cruises for those that want to be out on the water. They have daytime and sunset cruises. 

You can easily head back to Chicago in the evening if you want to since the drive is only about an hour and 40 minutes. Before leaving the area, make sure to walk around the city center, where there are some great boutique shops. 

lake geneva shoreline, boats in the water, chicago day trips, chicago road trips, day trips to chicago

Getting to Lake Geneva

Renting a car is the fastest and easiest way to get to Lake Geneva. It takes about an hour and a half when you drive along I-94 W and WI-50 W. There is also an option to take a train, but I don’t recommend it as it includes transfers, and the journey can take up to 3 hours.

2. Grab a Beer in Milwaukee 

If you want to head to another nearby city, you can head up to the state border and be in Wisconsin in about an hour and 35 minutes. 

Milwaukee has plenty of things to do, but beer lovers will love this city the most. Craft breweries can be found all over the city, along with microbreweries. Many of the older breweries have a long history and even offer historical tours. 

Here are the best places not to miss:

  • Lakefront Brewery: Offering seasonal beers with local ingredients, this brewery is one of the most famous in Wisconsin. They have a diverse selection of flavors. Everyone in your group should be able to find something they like, including those who are gluten-free!
  • City Lights: Famous for its coconut beer, City Lights is in a historic building that also offers tours. They have a really nice patio outside where you can see the Menomonee River. 
  • Eagle Park Brewing: This brewery has many different options, including milkshake IPAs, hazy IPAs, and hard seltzers. It’s a large brewery, so you can always find seating, even on the weekends or other busy periods. 
milwaukee skyline, sunset over the skyline, clouds streaking across the sky, giant boat in the harbor, places to visit near chicago, short trips from chicago

Getting to Milwaukee

If you have a car, it’s easy to get to Milwaukee in about an hour and a half using the I-94 W. You can also take a train, as Amtrak stations are in both cities. Hiawatha Service is the most common way to travel between the two cities.

3. Go Fruit Picking in Fenneville 

Around 2.5 hours from Chicago, Fenneville is one of the best day trips from Chicago. It’s in the fruit belt of Michigan, so it’s a great place for fruit picking. In the fall, you can pick fresh apples; in the summertime, you can get peaches and cherries. 

Pleasant Hill Farm and Crane Orchards are the most popular places for fruit picking. 

Before heading back to Chicago, stop by Crane’s Pie Pantry. It’s a beautiful winery and restaurant in a historic barn. They have amazing food and pies made with fresh fruit from nearby farms. 

Getting to Fenneville

The fastest way to get to Fenneville is to rent a car. The journey will take you about 2 hours and 20 minutes when you use I-94 E.

4. Visit Gurnee

Just one hour from Chicago, Gurnee is another of the best weekend road trips from Chicago. It’s home to Six Flags of America, so many rollercoaster fans come here for the weekend to get their adrenaline pumping. 

If you’re not an amusement park fan, there are many other things to do in Gurnee, including:

  • The Chocolate Sanctuary: This restaurant has a nice breakfast buffet, including freshly baked bagels. The chocolate-covered strawberries are a popular item on the menu. 
  • Illinois Beach State Park: Come here in the summer to lounge on the beach, pick wildflowers, and spot more than 600 different species of plants. 
  • Only Child Brewing Company: This brewing company has something for every palate, including IPAs, citrus fruit beers, and beers aged in wine barrels. 
  • Lambs Farm: A small farm that’s also an animal shelter, Lambs Farm is a nonprofit that employs people with disabilities. You can spend time with the animals, grab a treat at the bakery, and play mini golf. 

Getting to Gurnee

The only option to get to Gurnee from Chicago is to rent a car, as there are no good bus or train options. The drive only takes about 45 minutes on I-94 W, making it a super easy day trip.

5. Tip Toe Through the Tulips in Holland 

This small town in Michigan is 2.5 hours from Chicago. Spring is the best time to visit, so you can see the tulips in bloom. At the peak in spring, the town boasts over 4.5 million tulips. 

The best places to see the tulips are Windmill Island Gardens and Veldheer Tulip Gardens

There is also a tulip festival in early May that is worth checking out. You can try Dutch food, see traditional Dutch dancing, and even watch a few parades that go through the city center. 

There’s also the Holland Museum, which you should check out if you’re interested in Dutch culture and cuisine. 

Spring is the best time to see the tulips, but it’s not the only time of year when there are festivals. Come in late November if you’re interested in the Parade of Lights or Dutch Winterfest. 

bright yellow tulips in front of dutch architecture building

Getting to Holland

There are a couple of options for getting to Holland from Chicago. One is to rent a car, and the other is to take the Amtrak train. Many people choose to take the train as no transfers are, making it an easy journey.

The train will take about 3 hours. It can be pricey, though, with tickets costing up to $90 one way. If you travel with many friends, it might be cheaper to split the cost of a rental car and fuel.

6. See the Flowers Blooming in Chicago Botanic Gardens

For one of the best short trips from Chicago, you can drive about 35 minutes to get to the Chicago Botanic Gardens. The landscaping is beautiful, and flowers bloom through spring, summer, and early fall. 

The botanical gardens are divided into thirty separate smaller gardens, all with distinct flora and fauna. 

Once you get to the gardens, you can download an app on your smartphone that guides you down the different pathways in the park. A voice narration provides information about the different flowers and garden designs. 

On-site, there is a small restaurant and cafe. There is also a bike rental shop, as some parts of the gardens allow cycling. 

Chicago Botanic Gardens is located at 1000 Lake Cook Rd, Glencoe, IL 60022, United States. They’re open from 10 a.m. to 6 p.m. Tickets start at $11.95. 

Getting to Chicago Botanic Gardens

You’ll definitely need to rent a car to get to Chicago Botanic Gardens from Chicago. The easiest way to get there is to use I-94 W and then get off onto US 41. It will take you just under 30 minutes to get there.

7. Go Horse Riding in Indiana Dunes National Lakeshore 

If you’re interested in a one-day beach trip from Chicago, head to the Indiana Dunes National Lakeshore, just an hour outside of Chicago. The shore is about 15 miles long and is perfect for relaxing when the weather is warm. 

There are also many trails around the shore to go hiking, biking, or horse riding. If you’re interested in birding or want to explore more of the lakeshore, stop at the visitor’s center and ask to go on a walking tour led by one of the park rangers. 

Indiana Dunes National Lakeshore is located at 1215 N State Rd 49, Porter, IN 46304, United States. It’s open from 7 a.m. to 11 p.m. Entrance tickets are $15 if you don’t have a car and $25 if you do have a car. 

indiana sand dunes national park shoreline, grassy field with trees in the background

Getting to Indiana Dunes National Lakeshore

There is a bus option to get to the lakeshore, but I don’t recommend it as it makes the day very long, and the buses don’t come super often. Renting a car is your best option, and it takes about 45 minutes to get here from downtown Chicago.

8. Tour the Anderson Japanese Gardens 

For another of the best Chicago road trips, head about an hour and 40 minutes outside of the city to Anderson Japanese Gardens. You can walk down the quiet, peaceful trails and see the gardens John Anderson and Hoichi Kurisu designed. 

You can also take a guided tour. The guides can tell you more about the plants and the garden’s design. 

Open in 1978, the gardens were designed using different plants, water, and stones to provide a more authentic Japanese garden feeling. 

The Anderson Japanese Gardens are located at 318 Spring Creek Rd, Rockford, IL 61107, United States. Hours vary by season, and they are closed during the winter months. Tickets are $11.  

Getting to Anderson Japenese Gardens

To get to the gardens from Chicago, your best choice is to rent a car. If you drive along I-90 W, you can reach the gardens in about an hour and a half.

9. See the Discovery Center in Rockford, Illinois

Anderson Japanese Gardens is located in Rockford. So, after visiting the gardens, you can stay a little longer and explore this charming small town. 

This is a great place to visit if you bring the kids, as there are many family-friendly activities like the Discovery Center Museum.

You need to make reservations online before coming. There are over 250 exhibits to visit, so you can easily spend a whole day here. 

If you’re not with the kids, head to Prairie Street Brewing. Along with great local beers on tap, they also have bar food with a twist. Try the spicy mac ‘n’ cheese or the Asian street tacos. 

Getting to Rockford, Illinois

If you don’t want to rent a car, you can take a bus from Chicago to the Amtrak Station in Rockford. From there, you must take an Uber to the Discovery Center Museum.

If you choose to rent a car, you can drive directly to the Discovery Center on I-90 W.

10. Go to a Festival in Cedarburg, Wisconsin 

This cute town in Wisconsin is about 20 miles from Milwaukee and 2 hours from Chicago. Many family-owned places exist, including the wine bar Cedar Creek Winery and a famous candy apple store called Amy’s Candy Kitchen.

The city is also well known for having festivals in the fall that attract many different visitors, including Oktoberfest and the annual Wine & Harvest festival.

Getting to Cedarburg

Definitely rent a car to get to Cedarbug, as bus and train options are super limited. it takes about 2 hours to get to Cedarburg from Chicago.

11. See Bison at Midewin National Tallgrass Prairie

You might already know that Illinois is nicknamed the “prairie state.” This is because there are tons of uninhabited land where animals, like bison, roam freely.

To get a close-up look at these incredible animals, head to the Midewin National Tallgrass Prairie.

The place is pretty large, so you might have to spend several hours looking for the bison. Most travelers can spot them from the Iron Bridge Trailhead. You should also consider bringing a photo lens that can zoom in or a pair of binoculars so you can see the animals better.

There are also a few hiking trails throughout the prairies where you can see other wildlife and their natural habitats.

Getting to Midewin National Tallgrass Prairie

The only way to get to the prairies is to rent a car, as they are in a pretty rural area. You can drive along I-55 S to get here, and the journey will take about an hour.

three bison roaming in the prairies, one laying down and the other two eating

Top Things to Do in Chicago

Planning on spending time in Chicago in between a few fabulous day trips? Here are the top things to add to your Chicago bucket list:

  • The Art Institute of Chicago: All art lovers should head here on their first day in Chicago. The permanent exhibits showcase pieces of art from all over the world. Make sure to check the calendar to see which rotating exhibits they have while you’re visiting. 
  • Cloud Gate: This is the famous mirror bean that you have probably seen many photos of while planning your trip to Chicago. It’s an iconic piece of Chicago history that is worth seeing. 
  • Millennium Park: The perfect place in the city for people-watching, grabbing a snack, and relaxing. In the winter, there is an ice rink where you can go skating. 
  • Eat deep-dish pizza: Eating pizza is a must while in Chicago. The best places to enjoy pizza in the city are Giordano’s and Lou Malnatis
  • Gaze at the architecture: One of the first things you’ll notice when walking around Chicago is the beautiful buildings. Try to join a walking tour so you can be sure not to miss any of the best architectural spots. 
  • Hit the clubs: Chicago is known for having an amazing nightlife scene. If clubbing isn’t your vibe, there are many laid-back bars around the city as well. Raised Urban Rooftop Bar is one of the best places to drink, with nice views of the skyline. 
chicago bean, cloud gate, reflection of the buildings in the metal bean

How to Get to Chicago 

Chicago has a huge international airport, making the city very accessible for domestic and international travelers. Chicago O’Hare Airport (ORD) has daily flights from locations all over the world. 

You can find flights on American Airlines, Delta, and cheaper carriers like Spirit and Frontier. International airlines like KLM, Ethiopian Airlines, and Turkish Airlines also fly to Chicago. 

When to Visit Chicago 

Chicago has brutally cold winters, so it’s best to avoid coming to the city during that time. The months with the mildest weather include April through October. If you really hate chilly weather, the latest you should come is in September. 

The summer and early autumn months also have many different festivals making it a great time to be in the city. 

Don’t Miss These Incredible Day Trips from Chicago! 

From small local towns to state parks to famous botanical gardens, there are some amazing day trips from Chicago. While many more didn’t make this list, these are the ten best day trips to check out when you’re in the Chicago area. 

Are you heading to Chicago? Which of these day trips are you going to take first?

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