Road Trip Ideas from Chicago

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Chicago, known as the Windy City, has been home to some amazing innovations The Twinkie appeared in 1930 and the first all-color TV in 1956.

Chicago has other claims to fame as well.

The Chicago River runs backwards, the city has the 2nd largest public transportation system in the United States.

There’s an underground pedestrian system covering over 5 miles in the central business district. 

If you live in Chicago, you’re fortunate. Within 12 hours from your front door on the East Coast or in the Midwest, you can find something for everyone. Whether you’re taking a week-long road trip from Chicago, or just heading out for one day, you will be pleasantly surprised at what you discover. 

7 Day Road Trip Ideas from Chicago

Mt. Rushmore

One of the possible road trips from Chicago is going to see Mount Rushmore in South Dakota. This is at least a 16 hour drive so you’ll want to give yourself two days traversing highways. Some places you can stop to rest include Sioux City or Sioux Falls (depending on which roads you’ve chosen).

Mt. Rushmore is South Dakota’s tourist-central The images of President Washington, Jefferson, Lincoln and Roosevelt stare out across the badlands. While the carving of this monument began in 1927, it wasn’t finished until 1991.

It took removing 400,00 tons of rock from the mountainside to make this amazing carving complete. At night you can enjoy an illuminated view. If you want a closer look take the Presidential Trail (just over ½ mile long). 

Badlands National Park, nearby, has herds of bison and a unique landscape due to erosion in the sand and clay. There are plenty of parking places. If you enjoy hiking there are marked trails throughout the grassland park. The visitor’s center offers maps

Wind Cave National Park

Wind Cave National Park also in South Dakota is a slightly shorter drive, a mere 14 hours . It’s well worth the trip. The cave system is one of  the largest in the world. Within there are boxwork structures,

delicate mineral patterns looking like honey comb dotting various caverns. Various types of guided tours are available depending on your level of ability. Nearby you can enjoy hot springs, hiking trails, areal tours, animal attractions, and the World Fossil Finder Museum.

The National Music Musem

Located in Vermillion, South Dakota this road trip from Chicago spans about 9 hours one way. If you are a music lover, you can see instruments from various historical periods, gathered from all over the world.

Nearby you can see the Black Hills (just 5 miles away), and Spirit Mound where Native Americans believed little people lived. There are also great brew pubs and vineyards.

New York City

Driving to New York City takes about 13 hours. You can stop along the way in Cleveland or Pittsburgh. The tough part once you arrive is figuring out what to see. New York offers so many sights and experiences. 

First stop? How about the Statue of Liberty? The statue is among the world’s tallest rising 152 feet in the air, and remains a symbol of freedom and hope.

Alternatively you could head to Central Park for a much needed leg stretch. All around the park there are free venues. Check out the Strawberry Fields or the Central Park Zoo.

Next in NYC you could move on to Rockefeller Center. The Center is a huge entertainment center complete with shopping, outdoor ice skating in winter, and an observation deck. The view can’t be beat! Get pictures of yourself next to the Bronze sculpture of Atlas. 

Where else to go? So many options! If you love art, the Metropolitan Museum of Art (fondly known as the Met) has two million pieces for your viewing pleasure. Maybe take a lazy walk down Broadway, or shop on 5th Avenue. 

New Orleans

For a completely different experience drive 14 hours to New Orleans (two day drives are recommended). New Orleans has a quirky edge and impressive Cajun cuisine. You can go on a ghost tour, stopping at the Voodoo Museum, take in a night of jazz, or just enjoy the vast variety of architecture.

The vast majority of the tourist attractions lie in the French Quarter, along with horse drawn carriage rides and Bourbon Street, filled with lights, iconic bars, concerts and all manner of revelry (take a nap before you go!).

Weekend Road Trips from Chicago

When you are looking for something less ambition consider sneaking away from Chicago to Lake Michigan, just 90 minutes away. The influence of beer on this region is unmistakable, being the home of Pabst Brewing and Miller Brewing.

The public museum in Milwaukee has recreated streets from the city’s 19th century history and a butterfly garden. Motorcycle lovers, this is the home of the Harley-Davidson.


It takes three hours to reach Indianapolis by car, and there’s so much to do that a weekend may not cover it all. Head to the Children’s Museum enjoy thrills at the Indianapolis Speedway, or wander the Indianapolis zoo, just for starters.

The zoo, in particular, is a spectacular attraction complete with an aquarium and botanical garden. There are 2,000 animals and 2,000 plant varieties. You can see an Asian forest or African Savannah. When you need a break, there are food venues scattered throughout ranging from a classic burger to something gourmet.

Lake Genevia

About 90 minutes from Chicago, Lake Geneva is a lovely summer retreat. The beaches are sublime, and for the more adventurous, try zip lining. During winter here are Ice Castles that look like they came from a fairy tale. If you’d like to relax with some golf, Lake Geneva boasts some of the best golfing destinations available in the Midwest region. Beyond this, Lake Geneva offers paddle boarding, horseback riding, boat rentals, and a trolley museum.

Day Road trips from Chicago

You’ve got a day off coming up and want to avoid doing dishes? It’s time for a road trip! Consider South Bend In for a visit to the History Museum and Farmer’s Market.

Nibble on some warm bread and gather fresh vegetables for cooking at home.

Rockford IL

Alternatively, hop in the car for a 90 minute jaunt to Rockford Illinois. This is a great destination if you have kids. Take them to the Discover Center Museum , home to three hundred hand’s on activities.

Not too far from here get a zen moment at The Japanese Garden. Relaxation was never more beautiful.  

Frank Lloyd Wright Home and Studio

One of the most famous names in American Architecture, Frank Lloyd Wright has building and homes in numerous cities. The Studio has preserved Write’s working ambiance. Today his home is a National Historic Landmark and Trust.

Your road trip will only be a half hour, and while you’re in the area check out the Oak Park Conservatory with various ecosystems.

Road Trip from Chicago to California

This is not a road trip for the faint of heart. If you follow the famous Route 66, you roll over 2,500 miles of road spanning 8 states. The landscape ranges from ultra urban and farmland to mountains and deserts.

You could go the “faster” route (2,000 miles) via I-80, but why not go for the gusto? You have 41 hours to eat, drink, sight see, and have fun. 

You’ll be moving through Ilinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona before reaching the California border. Whew! There is limited space in this article, but we’ll try and give you some great ideas.

You’re beginning in your home state. You’ll go through your capital and Springfield before heading over the border to Missouri. It’s a pretty drive, but if you’re going in winter take is slow.

Take a picture of the famous sign saying Route 66 Eastern Terminus because it’s the last stop on the route if you are traveling from Los Angeles.


In Missouri you’ll see a true American slice of life (probably complete with apple pie in some locations). Many gas stations along the way have an old-time feel. Hey, wanna see the world’s largest catsup bottle (170 feet tall)? Stop in Collinsville.

Not your bag of fries? How about the Largest Rocking Chair on Route 66 instead?


This portion of your road trip from Chicago to California is rather laid back. You can visit the Rainbow Bridge in Baxter Springs, just slightly off the route. If you’d like to shop a bit, the Williams Store in Riverton has food and souvenirs. We recommend the pink flamingos. 


Oklahoma has tons of historic, cozy sights, especially in Oklahoma City and Tulsa. Since we are on a bigger-is-better theme here, stop at Pop’s 66 Soda Ranch in Arcadia to see a 66 foot tall soda bottle.

While you’re there,  have a light lunch and treat yourself to any of the 650 types of soda for when you get thirsty.

Keeping with the trend, you can take pictures of a 90-foot totem pole in Chelsea, built in 1937. It is the world’s largest totem pole.

The park surrounding has exhibits of hand carved fiddles and other folk art features. Or, how about an 80-foot whale?


YeeeHaw Y’all! The Panhandle state has ranches, but not always filled with horses. The Cadillac Ranch in Armadillow has classic Cadillac dotting the land. What makes it special?

The cars are buried head-first in the dirt, and stand like an automobile Stonehenge.  You are now half way through your journey congratulations!

New Mexico

New Mexico, at least initially, is nothing to write home about until you get to Albuquerque. Pause for a moment and enjoy the natural beauty of Cibola National Forest before going further.

If you don’t mind a quick side trip, stop in Santa Fe and see the oldest house in America, built in 1625.


Don’t leave Arizona without seeing the Petrified Forest National Park, followed by the Grand Canyon, one of the 7 wonders of the world, with rich rustic colors.

While you’re at it, head over to Meteor Crater National Landmark just south of Winslow (only 6 miles off the beaten track). The crater was formed some 50,000 years ago.



Take a deep breath. You are at the other end of Route 66 where it turns into highways entering Los Angeles. California is a pretty big state, so your choices of places to see and things to do is nearly limitless.

If you’re looking for some traditional stops, consider the Mojave National Reserve, some 1.6 million-acres in size

From natural to spectacular, move on to the Broadway Theater district, a nucleus for social interaction and events. Experience Hollywood at its best.

For a different kind of thrill, there the Santa Monica Pier with an amusment park featuring 12 rides, including a solar powered Ferris Wheel. When you get hungry, the Pier has a great slection of fresh seafood.  

If you plan to stay for a while you can move  beyond this hub, but you still have 2,500 miles to go to get home! Enjoy!


I'm the owner of Beast Auto. I live in Phoenix, Arizona. I love anything automotive related, and taking road trips all across my beautiful state.