Whether you live in Chicago or will be flying in, the city is a great starting point for many epic road trips. While there’s plenty to see in the windy city itself, its position on the east coast makes it ideal for those who want to start a road trip, whether you’re going to go full Jack Kerouac and drive across the USA in a Limo Find, or just spend a couple of days exploring. Here are some amazing road trips from Chicago.

1. Historic Route 66

If you’re going to get your kicks on Route 66, as the old song goes, the classic way to drive this iconic road is to start in Chicago. Technically, you can drive from Chicago to Los Angeles on Route 66 in four days, but that’s without any stops or time to take it all in.

The best way to undertake this epic road trip is to get the right vehicle. Renting an RV is probably the best option for an extended trip. It’s not complicated to find various RVs and motorhomes for rent around Chicago, which would allow you to travel in comfort and would also mean that you always have somewhere to stay along the way. It can also work out cheaper than staying in motels and means you have extras like cooking facilities, so you aren’t spending weeks eating out for every meal.

Most people take 3-4 weeks to do Route 66 if they drive the entire historic route, although you could potentially do just a fraction of the drive and focus more on areas you are interested in. The choice is yours.

Route 66

2. The Lake Michigan loop

Chicago is right on the shores of Lake Michigan, and while there’s not a road that loops all the way around the lake, you can follow the small back roads and see some of Michigan and Wisconsin, before coming back to Chicago. It’s about 15 hours of driving overall, but you could easily break this down over several days and see:

  • The Grand Rapids
  • Little Traverse Bay
  • Northern Michigan
  • Green Bay
  • Milwaukee

This itinerary would then take you back into Chicago.

This is a fun area to explore as there are lots of lakeside towns, places to hike, as well as fish, wildlife, and endless natural beauty. Along the way, there are also some charming cities to stop in too. Lake Michigan can have very remote areas, so it’s worth renting an RV if you don’t like camping; otherwise, it can be hard to find places to stay.

3. Niagara Falls

The Niagara Falls are about an 8-hour drive from Chicago. This can be longer if you stop in some of Michigan’s small towns, or even visit Detroit to visit the museums or take a music-themed tour.

There are two towns known as Niagara Falls, one in upstate NY, and one over the border in Canada. In general, most people agree you get a better view of the falls from Canada, although, on the US side, you can get closer. Niagara Falls in Ontario is also more of a tourist destination, so as well as visiting the falls, you can:

  • Visit an observation tower for panoramic views
  • Visit indoor waterparks and theme parks
  • Ride on the Niagara Skywheel
  • See musicals and family shows
  • Visit casinos

While you’re visiting Niagara Falls to see the falls themselves, there’s actually a whole lot of things to do in the area, and it has become a major family-friendly destination.

4. Grand Rapids

Just under three hours by car, Grand Rapids in Michigan is a popular weekend break for Chicagoans who want a change of scenery. Grand Rapids has become an arty, cultural city in recent years, with hipster neighborhoods and a thriving foodie scene. There’s plenty to do in Grand Rapids, from hiking and sailing to art museums, craft beer tastings, family days out and live music, so if you have some time in your schedule, try to fit in a couple of days at least.

5. Monroe

Drive a couple of hours from Chicago to Monroe and you’ll feel like you’ve been transported all the way to Switzerland. That’s because this quirky little town was once a Swiss colony and is now the Swiss cheese capital of the USA, which means you’ll see lots of wooden chalets and influences from the area. There are lots of local restaurants that serve dishes smothered in Swiss cheese, as well as shops selling chocolates, crepes, and other delicacies. You can also visit the National Historic Cheesemaking Museum, which is a fun day out and full of local history.

6. Holland

Another local town with a European influence is Holland, which sits on the banks of Lake Macatawa, about a 2-hour scenic drive from Chicago. Holland has all the charm of a European country, and as you may have guessed, used to be colonized by the Dutch. There are quirky, Dutch-style houses, colorful buildings, and even windmills. Tulip Time also happens every Spring, where the town is covered in colorful flowers with lots of floral-themed events.

7. Indiana Dunes

The Indiana Dunes sit on a 15-mile stretch overlooking Lake Michigan, with soft sands surrounded by pine forests. Being just an hour away from Chicago by car, expect to find it very busy during the summer and on major holidays, but the further away you walk from the parking lots, the more space you’ll find on the sands. You can take a dip in the clear waters of Lake Michigan, go sailing and enjoy lots of water sports during the summer.

Winter is also a good time to visit Indiana Dunes, as the sloping sands are covered in snow, so you can snowshoe, cross country ski and enjoy lots of other winter sports while taking in the amazing views over the frozen lake.

Chicago is a great starting spot for road trips, especially in the with a position on the east coast that’s well connected to the rest of the country. Whether you decide to go on a multi-week RV journey cross-country, or you just want to go away for the night, there are plenty of ways to hit the road and see more.