Fantastic Road Trips from Chicago for All

Anna Johnson

October 5, 2023

Reading Time:- 6 minutes

Road Trips from Chicago

In the hot summer months, cities like Chicago do not retain much of their charm. Thankfully, you can get on a fun road trip with your family or friends for a week or more than that. The best road trips from Chicago do not involve a lot of travel and are ideal for a weekend or a week’s getaway.

You can engage in many great activities in places like Wisconsin, Indiana, Ohio, Kentucky, Missouri, and more. The possibilities for car vacations are practically endless. It majorly depends on the distance you can drive and the time you have.

This post will give you some great road trip options from Chicago area.

Best Road Trips from Chicago

Are you looking for the best road trip for a week or those for couples from Chicago? The following are some of the best trips from Chicago area that you can enjoy.

Lake Geneva

Lake Geneva is the perfect place to reach through a car drive. It’s a beautiful lake town that functions as a popular getaway for almost every person in Chicago and, even tourists. Located in south-eastern Wisconsin, Geneva Lake Shore Path is one of its famous attractions. A visit to Lake Geneva will surely make up for one of the memorable family road trips from Chicago.

Starved Rock State Park

Situated at a distance of just one hour and 48 minutes from Chicago, Starved Rock State Park has more than 13 miles of trails. It is one of the best road trips from Chicago for a week for adventure enthusiasts. This trip will make you witness nature in all its glory. It has stunning glacier-carved canyons, which is a reason for its popularity among campers.

Allegan County in Michigan

Are you looking for a road trip from Chicago to escape the scorching heat of summer months? If yes, then jumping into Lake Michigan will be ideal. Besides, this place also has several small towns, such as Holland, Douglas, and Fennville. Fennville is full of fruit orchards, berry farms, and vineyards. On the other hand, Douglas and Saugatuck are pleasant lakeside towns with stunning downtown areas.

Oregon in Illinois

Are you searching for the best road trips from Chicago by car that don’t take more than 3 hours? Take a family road trip to Oregon. Here, you can stay at any of the log cabins and check out the Nachusa Grasslands. It’s a wonderful site seeing Bisons roaming free. Hikers can hike the White Pines State Park. This place is perfect for families and kids alike.

New Buffalo in Michigan

New Buffalo comes on the list of the best road trips from Chicago for couples. It’s situated at the entrance to miles of sandy dune-backed Michigan shoreline. The place offers many outdoor adventures and water sports. From public beaches and quaint shops to wine trails and breweries, you will simply love this place.

Related Article – How Much Is Hertz Car Rental Deposit 

10-Hour Road Trips from Chicago

Great places that are about 10 hours from Chicago include New York, Washington DC, Charlotte, Birmingham, Little Rock, and more. If you are planning for a one-week or seven-day road trip from Chicago, these places are the best ones.

  1. New York: This place has various great staying places and things to see and do. You can stay at The Plaza and engage in activities at the Central Park. Take a tour of the Statue of Liberty one day or explore The Metropolitan Museum of Art. When you feel the need to snack, head over to places like Katz’s Delicatessen or Shake Shack.
  2. Washington DC: Washington DC is replete with crucial national landmarks and insightful museums. From the sitting statue of Abraham Lincoln to the political icon of the White House, there’s much to experience here. The nightlife is captivating, and for shopping the National Mall is the best. If you want to engage in songs, dances, and casual conversations, participate in the Meridian Hill Drum Circle Event. It’s a traditional Sunday event that began over 45 years ago and still continues.
  3. Charlotte: Charlotte is the biggest North Carolina city. It offers exciting attractions to tourists and residents alike. The place is nestled between the stunning Appalachian Mountains and the serene NC beaches. The 15-foot majestic bronze statue of Queen Charlotte at the airport of Charlotte Douglas is one of the major parts of the city’s identity.
  4. Little Rock: Going to Little Rock will certainly prove one of the best road trips from Chicago. It is dotted with green spaces and gives visitors various options to bike, hike run, and walk. They can do so on the trail of the Arkansas River. You can get a glimpse of the entire downtown Little Rock from the Pinnacle Mountain State Park. It is the highest point in the entire Central Arkansas.
  5. Virginia: Virginia is known for many things, such as the beautiful Appalachian Trail, presidential homes, and the Arlington National Cemetary. It has Jamestown, which was the first permanent settlement of the English in America. You can stay at places like the Peaks of Otter Lodge. There are various things to see here. One of them is the Great Falls National Park. A great place to eat is the Pita House.

A Like Post – How to Rent a Jeep in Hawaii

Wrapping up

There are many road trips from Chicago that you can take to spend time alone, with family, or with your partner. These trips will take you to mesmerizing places. You can be a part of a myriad of activities according to your liking there. Use any one of the options mentioned above and start planning a fabulous trip.

Frequently Asked Questions

  1. Which places can I go in a 5-hour drive from Chicago?

Places like St. Louis in Missouri, EAU Claire in Wisconsin, Traverse City in Michigan, and Cincinnati in Ohio are all five-hour drive from Chicago. They have gorgeous views, popular beaches, and adventure activities to discover.

  1. Which major cities are near to Chicago?

Many major cities are near Chicago, and they are ideal to escape the daily grind of life. These include Berwin, Oak Park, Aurora, and Joliet. All these cities are around 12 to 42 miles from Chicago.

  1. Which cities are 4 hours away from Chicago?

There are many great destinations that are not more than 3 or 4 hours from Chicago. The best ones are in Wisconsin, such as Madison and New Glarus. Indianapolis and Quad Cities in Illinois are also 3 hours away from Chicago.

  1. What are some good day trip ideas from Chicago?

You can go to various places near Chicago for a day trip. These include southern Michigan, Springfield, and Rockford in Illinois, and South Bend in Indiana. All these cities have great views and good staying places.

Category: Industry News


Write By

Anna Johnson is a seasoned writer at, specializing in delivering unparalleled insights on the art of car rental. With a robust educational foundation in Business Administration and over a decade of immersion in the travel industry, Anna harmonizes expertise and enthusiasm to offer invaluable advice for seamless car rental experiences.

Popular Post

SpinnyWheels March 4, 2023

How Much Is Hertz Car Rental Deposit [Recognize Cost]

Here, we'll answer your question about how much is Hertz....

SpinnyWheels February 24, 2023

Everything You Need To Know About “Car Rental Age California”

In this blog, you will get information about “Car Rental....

SpinnyWheels March 30, 2023

“Does Enterprise Rent Electric Cars” [Step-by-Step Guide]

Are you finding the answer to the “Does Enterprise Rent....


We are legit information transmitter regarding Car Rental Services. We work solely to help you choose affordable car in your location. With many options, choosing one is difficult but we make it easy for you by providing all the information regarding a particular Car pool service. Also, we are not partnered with any brands, companies, or any third party discussed within the pages.

© All Rights Reserved.