There are a lot of great destinations from Chicago! If you have a day or a week, these interesting cities and attractions are great places to visit on a road trip this summer.
When you are planning a vacation on a budget there there three factors to consider:
Gas
Food
Lodging
You have control over all these costs, but gas will cost what gas will cost. You have find something closer to home.
I have a list of destinations that can be exciting no matter how close or far from home your budget can carry you.
Day Trips from Chicago
These trips will take about an hour from the city and include some really cool sites to see.
The Vine Martini and Wine Bar
In Greyslake Illinois The Vine is a very popular bar. The relaxed atmosphere of The Vine makes it a great place to visit from Chicago.
Right down the street there is a great burger place, Twisted Burger and Emil’s Tavern. A great place to spend the evening with friends.
Cedar Lake (Indiana)
Cedar Lake is a great trip for hunting for antiques. The Old Goat’s market is a good first stop and you can enjoy learning about the area at the Cedar Lake Historic Museum.
There are a number of other antique and resale shops for a day of deal hunting.
Michigan City
Michigan City is just a short drive from Chicago and you can find Casinos, restaurants, outlet shopping and you will cross state lines!
If you are not into gambling, the lighthouse museum is a high quality educational trip and the outlet shopping is a great girls trip idea. Michigan city is an exciting day trip from Chicago.
2-3 Hour Trips from Chicago
A two hour trip is a really good distance for traveling with kids or young babies. Experienced travelers often travel for 2-3 hours max between stops.
Take a page from their book and stop before you get too tired of driving.
Menomonee Falls
Menomonee Falls is a beautiful destination. The falls are man made waterfall located in Mill Pond Park. The city was once home to a large sugar mill.
There are a lot of beautiful walking trails, ponds and river walks to enjoy in Menomonee Falls. There are also sunset beer garden events in warm weather.
Crane Orchards U-Pick and Corn Maze, Fennville, Michigan
A great fall destination, the Crane Orchards and Corn Maze in Fennville Michigan is a destination worth the drive.
Be sure to pack your walking shoes and enjoy picking cherries, peaches, apples and pumpkins in season. You can find their seasonal fruit page to let you know what is available to pick.
I love marking apple picking on my family’s calendar each fall. It is a beautiful memory and such a fun day.
Davenport Iowa
Right on the banks of the Mississippi Davenport is a great small city. Davenport is considered one of the Quad Cities.
This area offers riverfront dining, walking trails, shopping, theater and museums.
The Adler Theater offers comedian tours, live music and Broadway shows. Follow up your show with a river cruise and dinner.
This vacation is really shaping up and you drove less than 150 miles!
Indianapolis, Indiana
There is a large museum in Indianapolis that contains the best preserved T-rex in existence, your dino lover will never forget this three hour drive out of Chicago.
The museum associate with the Indianapolis Speedway is engaging even if you have never seen a race. When the track is not in use you can take the bus tour of this iconic track.
Monument circle in the heart of town hosts a farmer’s market, food trucks, coffee and restaurants. This busy area of town has plenty to see and do.
3-5 Hour Trips from Chicago
Three to five hours is the longest drive I would recommend that you drive without stopping, but you will feel like you really got away.
If you are traveling with kids I recommend that you read this post about how to plan stops with kids.
Bowling Green, OH
Bowling Green is a great place to attend really great events and festivals. The National Tractor Pulling competition is hosted here and the Great Black Swamp Art Festival.
They have a wonderful summer activity calendar that is sure to offer something worth seeing.
Bloomington, IN
If you would like a slower paced trip, head to Bloominton. The small town feel offers plenty to see and do.
Art museums, sculpture gardens and science museums offer plenty of things to do for the whole family.
The Wonder Lab Science Museum is a hands-on science museum for the whole family and it would make a great family event.
St. Louis, MO
Our family has taken several trips to St. Louis and you can read about our favorite STL destinations in the linked post. There is no limit to what you can do in St. Louis.
When you visit St. Louis you will want to see the Arch, the gateway to the West. The improved grounds are a lovely place to walk and read more about American history.
There are also a few foods you will want to try while visiting the city:
Frozen Custard
Toasted Ravioli
St. Louis Style Pizza
The first time I tried pizza from Imo’s Pizza I was surprised. It is a memorable experience, give it a try.
6-8 Hour Trips from Chicago
Chicago is a great starting point when you want to explore America. If you can budget to drive six to eight hours you will be able to visit some iconic American cities and attractions.
Erie, PA
Erie has the best city website I have seen. There is so much to do in Erie, water parks, historic tours of Lake Erie and AA baseball.
Request a guide to Erie on their city website. It will give you the most information about how to spend your time in this vibrant diverse city.
Nashville, TN
Nashville is an unforgettable trip. There is so much to see and hear in Music City.
The Nashville Zoo is great day or night. Their night light display is a stunning event and a low stress evening event.
You may also choose to schedule your trip around their incredible Food and Wine Festival. The city has the best hotels and restaurants for any budget.
You will want to hear some music and venues abound. Check out the calendars for:
Storytellers Hideaway
Grand Ole Opry
Ryman Auditorium
RCA Studio A
Mammoth Cave National Park
Mammoth Cave National Park is a beautiful destination for camping, hiking, exploring and soaking in nature.
National Parks can book up quickly so check out my handy guide to when to book your road trip lodging.
Large families or large groups will enjoy the flexible lodging options in National Parks. I highly recommend this for a family vacation.
Niagara Falls
Niagara Falls is a bucket list item for many people and it is just a few hours from Chicago!
This popular international tourist destination should be planned well in advance. Check lodging prices frequently and plan accordingly.
One tip for creating a low stress vacation plan is to hire a local guide. I highly recommend that you consider planning this trip with a travel agent or local guide company so that you can avoid getting stuck in a crowd and missing the experience you dreamed about.
Memphis, TN
Memphis is the home of bluegrass, soul music and rock and roll. This is an incredible destination for music lovers.
This is about as far south as you can drive from Chicago in 8 hours, so if you are looking to warm up Memphis is a great destination.
Festivals, concert cities and museums are all waiting in memphis.
They have several immersive art experiences as well as a trolly tour that is sure to delight.
Planning a Road Trip From Chicago
When you are planning a road trip from Chicago I recommend that you start at WithinHours.com this site will allow you to explore different travel radius options from your city.
This can help you uncover hidden gems that you may never have thought of in your area.
Follow up with this Road Trip Planning guide with a few printable worksheets that can help you stay organized and on budget.
