Best Day Trips From Chicago (That Are Less Than 2 Hours Away)

Looking to leave Chicago for the day or even a few hours? Fortunately there are many amazing places to visit in the Midwest near the city whether you love nature, beaches, cities or small towns. Here are the best day trips from Chicago all less than 2 hours from the city.

If you don’t have a car or would rather not drive, you can also visit most of these places by train or through a guided day tour.

Best Day Trips From Chicago

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.

Starved Rock State Park, Oglesby, Illinois

Distance from Chicago: 95 miles
Time from Chicago: 1 hour and 40 minutes
Address: 2668 East 873 Road, Oglesby, IL 61348

Starved Rock State Park is one of the best day trips from Chicago

Starved Rock State Park is one of the top attractions in the state of Illinois. The park is an ideal spot to enjoy nature and is filled with stunning sandstone canyons and beautiful waterfalls. This is a great place for hiking with 13 miles (21 kilometers) of trails.

In addition to hiking, visitors can enjoy outdoor activities year round, including horseback riding, ice climbing, cross-country skiing, as well as fishing, kayaking, rafting on the Illinois River.

Matthiessen State Park, Oglesby, Illinois

Distance from Chicago: 96 miles
Time from Chicago: 1 hour and 40 minutes
Address: 2500 IL-178, Oglesby, Ilinois 61348

Matthiessen State Park is not as popular or crowded as nearby Starved Rock State Park (less than 3 miles away) but it is just as beautiful with similar natural features such as canyons and beautiful waterfalls.

Oak Park, Illinois

Distance from Chicago: 10 miles
Time from Chicago: 15-20 minutes from downtown

Oak Park is a suburb on the outskirts of Chicago. The village prides itself on its racial, ethnic, socio-economic, and religious diversity. Downtown Oak Park is home to a variety of shops and restaurants but the main draw for visitors is the architecture.

Oak Park is home to the world’s largest collection of designed sites by Frank Lloyd Wright, the famous architect. Take a walking tour of the Wright District, an area of prairie-style homes designed by Frank Lloyd Wright. including the Frank Lloyd Wright Home and Studio, and Unity Temple, a Wright–designed church considered to be one of his most important structures.

For those who would rather not drive or take a rideshare, Oak Park is easily accessible from Chicago by train (Green Line and Blue Line on the CTA and Union Pacific / West Line on the Metra). Ridesharing services such as Uber and Lyft are also an option.

Rockford, Illinois

Distance from Chicago: 85 miles northwest from Chicago
Time from Chicago: 1.5-2 hours

Anderson Japanese Gardens in Rockford Illinois is one of the best day trips from Chicago
Image credit: Anderson Japanese Gardens

The most popular attraction in Rockford is Anderson Japanese Gardens, a 12-acre Japanese garden. If you have more time in Rockford before heading home, the city plenty of attractions including the Discovery Center Museum (a great family museum), Nicholas Conservatory and Gardens, Burpee Museum of Natural History, Tinker Swiss Cottage Museum and the Rockford Art Museum.

Cheap Car Rentals

Indiana Dunes, Indiana

Distance from Chicago: 50 miles
Time from Chicago: 1 hour

The Indiana Dunes National Park borders the State Park of the same name. The national park offers 15 miles of shoreline along Lake Michigan’s southern shore with wide sandy beaches and towering dunes. Hikers will enjoy 50 miles of trails over rugged dunes, mysterious wetlands, sunny prairies, meandering rivers and peaceful forests.

The three highest sand dunes are all in the Indiana Dunes State Park.

In addition to beaches and hiking, Indiana Dunes offers many outdoor year round activities including bird watching, fishing, cycling, horseback riding, kayaking and paddling, snowshoeing, and cross country skiing.

New Buffalo, Michigan

Distance from Chicago: 70 miles
Time from Chicago: 1 hour 15 minutes

New Buffalo, Michigan is a charming beach town on the shores of Lake Michigan. The beaches face west and have beautiful sunset views.

In addition to the beaches, a must see attraction is Galien River County Park, a beautiful park with boardwalk paths through the marsh.  For those that enjoy gambling, New Buffalo is home to the Four Winds Casino Resort.

New Buffalo has daily Amtrak service from Chicago on the Blue Water and Wolverine lines.

Milwaukee, Wisconsin

Distance from Chicago: 93 miles
Time from Chicago: 1 hour 40 minutes

This lively city is like a smaller less touristy version of Chicago.

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Amtrak Hiawatha train offers frequent daily service between Milwaukee and Chicago.

Lake Geneva, Wisconsin

Distance from Chicago: 83 miles
Time from Chicago: 1 hour 40 minutes

Lake Geneva Wisconsin day trips from Chicago
Lake Geneva is a resort city on the shores of Geneva Lake in southeastern Wisconsin. The area is a popular vacation destination for Chicago – wealthy Chicagoans built their mansions here during the Gilded Age.

Visitors can enjoy a variety of outdoor activities on the water, including boating, kayaking, paddle boarding, and cruises. There are also a petting zoo, waterpark, golf, hiking, zip-lining, spas, and more.

The highlight is the Lake Geneva Shore Path, a a 21-mile trail around the lake with stunning views of the forest, water and impressive waterfront homes. Visitors can hike, bike or take a cruise around the lake.

You can visit both Milwaukee and Lake Geneva from Chicago with this guided one day tour.

Pontiac, Illinois (Historic Route 66)

Illinois historic route 66 sign

Distance from Chicago: 100 miles to Pontiac

Historic Route 66 is a classic American road trip. Don’t have time to drive Route 66 all the way from Chicago to California? You can visit Pontiac and drive a portion of historic Route 66 on a day trip from Chicago.  Must see attractions in Pontiac include the IL Route 66 Association Hall of Fame & Museum, the Pontiac-Oakland Automobile Museum and the Route 66 Shield Mural.

You can visit Pontiac with this guided 1-Day Route 66 Tour.

Sunflower Fields Near Chicago (Summer and Early Fall)

sunflower fields near chicago

Distance from Chicago: Varies
Time from Chicago: From 40 minutes to 1.5 hours driving time depending on the field

Looking to enjoy some beautiful summer flowers or snap beautiful photos? There are several sunflower fields located near Chicago. Peak season to see sunflower fields is early July to late September, but some farms are expecting to have sunflower mazes open into October.

What are your favorite day trips from Chicago?

Planning a trip to Chicago? Check out my Chicago guides and itineraries:


Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.