Top Scenic Drives From Chicago

chicago day trips

You don't need to go far if you want to have a day trip from Chicago or a weekend getaway from the big city. A variety of award-winning parks, historic museums and sites that will recharge your life are within a three-hour drive or less from the "Windy City". Rent a car with VroomVroomVroom and start exploring!

Chesterton

indiana sand dunes on lake michigan shoreline

Situated just south of the stunning Indiana Dunes State Park, there is no shortage of natural beauty in Chesterton. Outdoor and beach aficionados, rejoice! Hiking and biking trails are only a few minutes away from fine beaches along the Lake Michigan shoreline. Do you like nature? Then come and visit the Coffee Creek Watershed Preserve, which includes the Chesterton Amphitheatre and Phillips Pond.

If you enjoy history, both the Commercial Historic District and the Westchester Township History Museum are worth visiting. For a delightful dining experience, eat at The Lemon Tree Mediterranean Grill or dine in at Third Coast Spice Cafe.

Travel Time: 56 minutes

Directions: Follow North LaSalle Street and take the ramp on the left towards I-90 E then merge right on Kennedy Expressway. Continue on Dan Ryan Expressway and keep left on Indiana Toll Road. Take the ramp towards I 94: Detroit then merge left on I 94 E. Drive for a few minutes and arrive in town.

Top Attractions: Coffee Creek Watershed Preserve & Commercial Historic District.

Woodstock

wooden shelves in the bookstore

Are you looking for an outdoor getaway, a fun retreat, or a culturally rewarding adventure? You're in luck! There's something to see and do in this charming town of Woodstock. Visiting the town's historic opera house which starred in the movie Groundhog Day should be on the top of your list. Each year, the town celebrates the Bill Murray film with pride and gusto.

If you see yourself to be in Woodstock during Groundhog Days weekend, sign up for the Guided Walking tour. Take the opportunity to learn the stories as told by people who were a part of the movie-making process. The annual Woodstock Folk Festival is another anticipated event usually held during the third Sunday in July. Searching for book-inspired treats? Visit this cozy bookseller Read Between the Lynes.

Travel Time: 1 hour and 22 minutes

Directions: Get on S Federal St / W Van Buren St / I-290 W/W Congress Pkwy. Take I-90 W/I-94 W/Wisconsin / IL-47 N / E South St/U.S. 14 Business Route.

Top Attractions: Woodstock Opera House, Read Between the Lynes Bookstore and Woodstock Folk Festival.

Ottawa

the starved rock state park in illinois

Only a 15 minutes drive from Ottawa via IL-71 W, find out why millions of people flock to see the spectacular Starved Rock State Park each year. Begin your epic adventure with a visit to the Visitors Center situated along the Illinois River area in the main park. The Illinois River provides boating and fishing with nice places to relax while the park has 13 miles of trails to explore.

Other fun things to do during your stay in Ottawa include taking a tour to one of Ottawa's greatest treasures - the magnificent Reddick Mansion and spending some time learning about the history at the Ottawa Historical and Scouting Heritage Museum. 

Travel Time: 1 hour and 23 minutes

Directions: Get on I-55 S/I-90 E/I-94 E and follow I-55 S/St Louis/Stevenson Expy and merge on I-55 S/Stevenson Expy. Take exit 90 and get on IL-23 S/Columbus St

Top Attractions: Reddick Mansion and Gardens, Ottawa Historical and Scouting Heritage Museum and Starved Rock State Park.

Lake Geneva

view of lake geneva in summer, wisconsin usa

The beautiful town of Lake Geneva in Wisconsin has a plethora of activities for visitors of any age. Don't miss checking out the Stone Manor, known as the granddaddy of all lakefront mansions on Lake Geneva. Adventure enthusiasts will enjoy some of the popular activities found in this area. These include downhill skiing, hiking, fishing, biking, boating, parasailing, canoeing and kayaking. 

Head to the Cornerstone Shop & Gallery for some unique accessories and accent pieces. For a fancy dinner, visit the famous Baker House and sample on their signature crab cakes and braised short ribs. Want to stay overnight? Lake Geneva provides guests a wide variety of accommodation options from luxurious spa resorts to lovely inns.

Travel Time: 1 hour and 41 minutes

Directions: Get on I-290 W / IL-53 N Lake Cook Rd W. US-12 W/Rand Rd W Case Rd, Cty V47/N Darrell Rd. Continue on IL-120 W/Rand Rd, State Rte 31 N/N Richmond Rd n US-12 W. Take 330A-330B for WI-50 W/WI-120 S / County Rd H S.

Top Attractions: Stone Manor, Cornerstone Shop & Gallery and Barker House.

Indianapolis

the famous indiana capitol building

You will pass by one of the largest city parks in the United States upon entering Indianapolis. The Eagle Creek Park is a perfect place to enjoy swimming, fishing, canoeing, sailing and hiking.

If you are an Indianapolis 500 fan, the iconic Indianapolis Motor Speedway is a must-see. This is your chance to know everything about race cars. Take a lap around the track and see the Indianapolis Motor Speedway Museum as well.

For something that's fun and educational, plan a visit to the Indiana State Capitol Building. Spend an afternoon in the White River State Park and have an artful experience by visiting the Congressional Medal of Honor Memorial.

Travel Time: 3 hours

Directions: From downtown Chicago, get on I-90 south and follow this route to Gary, Indiana. Take Exit 17 to I-65 south.

Top Attractions: Indianapolis Motor Speedway, White River State Park, Eagle Creek Park, Indiana Capitol Building and Congressional Medal of Honor Memorial.



Map of Chicago Day Trips

Do you know that you can download this map directly to your phone? Press the box symbol located on the top-right corner of this map to open in your Google Maps app. Now you can easily access this map on your next day trip in Chicago.




Other popular road trip locations