Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!
The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer.
Best Chicago Road Trips in Summer
If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans? If you’re thinking a little shorter, then read on…
1. Road 66
Distance: as far as you can go
No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!
Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.
2. Illinois’ Great River Road
Distance: 3.5-hour drive
In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.
Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes.
3. Lake Michigan to South Haven
Distance: 2.5-hour drive
Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.
There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?
To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two.
4. Shawnee National Forest
Distance: 6-hour drive
One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes!
Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.
Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area.
Best Chicago Road Trips in Winter
If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.
5. Grand Rapids
Distance: 3-hour drive
After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.
Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop.
Distance: 3-hour drive
Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.
Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.
Distance: 3-hour drive
When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.
From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!
Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.
8. Boyne Mountain Resort
Distance: 5-hour drive
Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.
While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes.
If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.
9. Apostle Islands
Distance: 7-hour drive
Does driving over ice count as going off-road?
It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!
Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay.
Day Road Trips from Chicago
10. Lake Geneva
Distance: 1.5-hour drive
Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.
Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.
Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!
11. Harbor Country
Distance: 1-hour drive
Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.
It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world.
12. Starved Rock State Park
Distance: 2-hour drive
Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.
It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views.
Distance: 2.5-hour drive
Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!
Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.
14. Elkhart Lake
Distance: 2.5-hour drive
I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.
You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!
Want a charming hideaway? This is it.
Road Trips 4 hours from Chicago
Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.
15. Ann Arbor
If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.
Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings!
16. Door Country
Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!
You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.
You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19th century.
For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round.
18. Richland County
To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.
The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?
You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way.
19. Huron-Manistee National Forest
Michigan really surprises us again and again!
Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers.
Road trips from Chicago
Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.
Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead.