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Lizzy Fay

June 14, 2019

21 Awesome Road Trips to Take from Chicago

Sometimes you just need a little break from the city. Fortunately, there are dozens of great road trips to take from Chicago with destinations less than three hours away. So grab a friend, your keys, and head outta town to any of these awesome destinations!

Behind the Wheel of the 2019 Mazda CX-5 SUV

Because I live downtown Chicago where everything is a quick walk or uber ride away, I actually don't own a car anymore. It's great for my bank account, but every once in a while, I wish I could easily hop in a car for a quick getaway. So when the opportunity came up to borrow a Mazda CX-5, I was stoked!

The 2019 Mazda CX-5 is luxurious without getting too pricy. Mazda lent me the signature-level CX-5 that came with Napa leather trim, Apple Car Play, and 360 monitors with front and back cameras that made parking a cinch! Thank you to Mazda for hooking me up with this sexy SUV so I could leave the city for a few days. But before I did, I teamed up with videographer Aron Ianchici to shoot the smooth-riding CX-5 in Chicago. Check it out, and let me know what you think on Instagram @heylizzyfay!

The Best Road Trips to Take From Chicago

#1 Hike at Starved Rock

Starved Rock (Courtesy Illinois Office of Tourism / ©Adam Alexander Photography 2016)

Location: 2668 E 875th Rd, Oglesby, IL
Time from Chicago: 1 hour and 40 minutes

Starved Rock is one of the top attractions in the entire state of Illinois! With stunning canyons and waterfalls, this outdoor adventure is a great escape from the hustle and bustle of the city. You can go fishing, boating and explore 13 miles of trails.

#2 Ride Roller Coasters at Six Flags

New Roller Coaster in 2019: Maxx Force (Courtesy Six Flags Great America)

Location: 1 Great America Parkway, Gurnee, IL
Time from Chicago: 1 hour

Six Flags Great America is an amusement park with thrilling rides, roller coasters and a 20-acre water park! Maxx Force, a triple-record breaking roller coaster opens Summer 2019. The coaster reaches 78 MPH in less than two seconds and features the highest double inversion at 175 feet and the fastest inversion of any coaster in the world!

#3 Enjoy a Concert at Ravinia

Courtesy Ravinia

Location: 418 Sheridan Rd, Highland Park, IL
Time from Chicago: 50 minutes

In the warmer months, check out a concert at North America’s oldest music festival. The 36-acre park is nestle in a wooded area in a northern suburb of Chicago. A range of artists like Lady Gaga, Yo-Yo Ma and John Legend have performed at Ravinia. Most people bring a picnic blanket, wine and snacks. There is even a train that stops right at Ravinia from Ogilvie Transportation Center.

#4 Pamper Yourself at the American Club

Location: 419 Highland Dr, Kohler, WI
Time from Chicago: 2 hours 30 minutes

This five-star resort is listed on the National Register of Historic Places and is recognized as one of the most luxurious resorts in the Midwest. Enjoy the spa, golf, exercise, indulge in food and wine, and explore the Kohler Design Center. The American Club is a relaxing getaway any time of year.

#5 Relax on Delavan Lake

Location: 2400 Geneva St, Delavan, WI  
Time from Chicago: 1 hour 45 minutes

Not far from Lake Geneva, you’ll find this quieter lake that is great for boating and fishing. Stay at the lakefront resort, Lake Lawn Lodge. It’s so peaceful on the lake. I’ve been going up here my whole life!

#6 Tour Frank Lloyd Wright Architecture in Oak Park

Frank Lloyd Wright Tours in Oak Park (Courtesy Illinois Office of Tourism / ©Adam Alexander Photography )

Location: 951 Chicago Ave, Oak Park, IL
Time from Chicago: 20 minutes

Oak Park is home to the world’s largest collection of renowned architect, Frank Lloyd Wright’s designs. Visit Wright-designed sites including his first home where he tested his design concepts. Guided and self-guided tours are available.

#7 Go on a Brewery Tour in Milwaukee

Photo via Urban Milwaukee

Location: 1872 N Commerce St, Milwaukee, WI
Time from Chicago: 1 hour 50 minutes

This lively city is like a more manageable, mini Chicago. You have Lake Michigan, museums, professional sports teams, hip neighborhoods, and excellent dining options. Home to Miller Coors, the city loves its beer ( and cheese)! Be sure to check out Lakefront Brewery and the Milwaukee Art Museum while you’re in town too. You can drive or take the Amtrak from Union Station.

#8 Go Shopping at Chicago Premium Outlets

Chicago Premium Outlets (Courtesy Illinois Office of Tourism)

Location: 1650 Premium Outlet Blvd, Aurora, IL
Time from Chicago: 40 minutes

Find deals on more than 170 stores at Chicago Premium Outlets including Kate Spade, Restoration Hardware Outlet, Adidas, Nike, Coach, Polo Ralph Lauren, and more!  

#9 Enjoy History & Shopping in Galena

Downtown Galena, IL (Courtesy Illinois Office of Tourism)

Location: S Main St. Galena, IL
Time from Chicago: 3 hours

This charming, historic town is a great place for shopping, culture, and dining. Galena is known for its well-preserved 19th century buildings and quintessential downtown. Visit the home of President Ulysses S. Grant, go antiquing, and eat at the famous Fried Green Tomatoes restaurant.

#10 Explore the Chicago Botanic Garden

Chicago Botanic Garden (Courtesy Illinois Office of Tourism)

Location: 1000 Lake Cook Rd, Glencoe, IL
Time from Chicago: 40 Minutes

Explore 30 distinct gardens in one place. Use your smartphone for a self-guided walking tour and admire the beautiful scenery. You can also find bike trails, bike rentals and birding classes at the Chicago Botanic Garden.

#11 Enjoy the Tranquil Anderson Japanese Gardens

Anderson Japanese Gardens (Courtesy Illinois Office of Tourism)

Location: 318 Spring Creek Rd, Rockford, IL
Time from Chicago: 1 hour and 45 minutes

For a peaceful escape from the city, head to Anderson Japanese Gardens. Master Craftsman Hoichi Kurisu designed this beautiful space. You can enjoy breakfast or lunch at the garden’s cafe.

#12 Get Active at the Indiana Dunes

Indiana Dunes Photo via: Travel & Leisure

Location: 1600 N 25 E, Chesterton, IN
Time from Chicago: 1 hour

The Indiana Dunes offer 15 miles of sandy beach and 50 miles of trails. It is recognized as one of the nation's National Parks! You can visit all year for hiking, biking, horseback riding, snowshoeing, and cross country skiing.

#13 Visit the Animals at Brookfield Zoo

Location: 8400 W 31st St, Brookfield, IL
Time from Chicago: 35 minutes

Meet more than 2,000 animals at this 200-acre zoo. Through the zoo’s Animal Encounters you can even pet a penguin or feed a giraffe!  

#14 Explore Nicholas Conservatory & Gardens

Nicholas Conservatory and Gardens near Sinnissippi Park in Rockford, Illinois. (Courtesy Travel Illinois by Alyssa Schukar)

Location: 1354 N 2nd St, Rockford, IL
Time from Chicago: 1 hour 50 minutes

With more than 11,000 square feet of tropical plants and flowers, the Nicholas Conservatory & Gardens is a beautiful place to explore. It sits along the Rock River in downtown Rockford, Illinois, so you can check out the city while you’re in town. I actually used to live walking-distance to the conservatory when I was a TV news reporter for Rockford’s NBC station!

#15 Take a Scenic Stroll through Morton Arboretum

Location: 4100 IL-53, Lisle, IL 60532
Time from Chicago 45 minutes

Walk along tree-lines trails to view more than 200 plants from all over the world. There are family-friendly events year round at the Morton Arboretum. Look out for six giant troll sculptures made of reclaimed wood. They make for a great photo!

#16 Climb the Warren Dunes

Location: 12032 Red Arrow Hwy, Sawyer, MI
Time from Chicago: 1 hour 25 minutes

Warren Dunes State Park is a 1,952-acre Michigan state park with large sandy beaches along Lake Michigan. I used to come here as a kid! Pack a picnic and plenty of SPF, and make a day of it!

#17 Go Wine Tasting in New Buffalo

Photo via Harbor Grand

Location: New Buffalo, Michigan
Time from Chicago: 1 hour 20 minutes

Head to Michigan for a quick and peaceful beach getaway. From hiking, shopping, and wine tasting there is plenty to do. This was my first trip with Kam and we had an amazing time going to the beach, renting bikes, and wine tasting! We stayed overnight in the cutest bed & breakfast.

#18 Take a trip to “Little Switzerland” in New Glarus

Photo via New Glarus Chamber & Tourism

Location: 2400 WI-69, New Glarus, WI
Time from Chicago: 2 hours 45 minutes

Take a trip to this charming little town and you’ll feel as though you’ve arrived in Switzerland.You’ll find unique restaurants, hotels, and shopping with a Swiss touch. The main attraction is the New Glarus Brewing Company which brews popular beer, Spotted Cow -- which is only sold in Wisconsin.

#19 Explore the State Capital of Wisconsin

University of Wisconsin Madison

Location: Madison, Wisconsin
Time from Chicago: 3 hours

Madison is recognized as progressive and green city with a lot to offer. You can visit the capitol building (which has a great farmer’s market around it in the summer), enjoy the arts, explore the outdoors including Lake Mendota, shop a super-cute boutiques and find the best brat. Madison is also home to the University of Wisconsin.

#20 Visit the Baha'i House of Worship

Photo Courtesy Illinois Office of Tourism

Location: 100 Linden Ave, Wilmette, IL
Time from Chicago: 45 minutes

The Baha'i House of Worship is the oldest surviving Baha'i House of Worship in the world and the only one in North America. The architecture is breathtaking and aims to illustrate Baha'i concepts of oneness. At the temple, there are no clergy, sermons or rituals, but it serves as a quiet space for prayer and service.

#21 Go Boating in Lake Geneva

Location: Lake Geneva, WI
Time from Chicago: Hour and 30 Minutes

With a lake that covers more than 4,500 acres, Lake Geneva is perfect for boating and kayaking. Take a walk on the 21-mile Lake Geneva Shore Path for gorgeous views the town's impressive waterfront homes. You can also enjoy zip-lining, shopping and dining. While I love visiting in the summer, Lake Geneva in the fall is exceptionally beautiful. (Check out my blog post about it!)

Hit the Road!

I hope these ideas inspire you to explore some of the attractions and cities around Chicago. Some of them are great day trips, but you can definitely turn many of these road trips from Chicago into weekend getaways. Are there any road trip ideas I left off the list? Leave them in the comments below!

Now, if you want to see more of the gorgeous 2019 Mazda CX-5, check out the photos below. The interior is just so chic! Thanks again to Aron Ianchici (@aronianchici on Instagram) for capturing these photos! Don't forget to pin this post for later.

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  • Road Trips from Chicago

SHOP THE LOOK

Comfy block heels: Nordstrom (on sale!) | Frayed hem jeans: Nordstrom | Tank Top: Express | Sunglasses: J.Crew (on sale!)

Thank you to Mazda for partnering with me on this post! Be sure to check out How to Get Around Chicago (advice & apps you need) as well as the VIP Ferris Wheel Experience at Navy Pier.

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Spending time at Theo’s great great grandparents Spending time at Theo’s great great grandparents’ place! His grandma spent summers here, I spent summers here and now he is taking his first overnight trip here. 🥰
Chicago museums are starting to reopen as we enter Chicago museums are starting to reopen as we enter stage four! 🙌 This photo was taken at @msichicago not long before lockdown. I was so happy to show Theo some of Chicago’s gems! 💎 Personally, I won’t be rushing back to anything indoors, but I’m glad to see things reopening and hope it can be done safely. By the way, @msichicago is expected to reopen this summer and you can get tickets now for @shedd_aquarium and @lincolnparkzoo. 🦥 What will you do now that we’re in stage four?
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Millennium Park is open again and today I stopped Millennium Park is open again and today I stopped by between doctor appointments (which I had been putting off!).You are supposed to wear masks in the park but there’s basically no one here so I found this spot to enjoy a quick lunch by myself. Today is the first time I left my baby with a sitter and the longest time I have been away from him. 😭 He is in good hands though. Poor guy hardly knows anyone but Kam and me. We kept him to ourselves the first 8 weeks of his life because we were scared of the flu. Then as soon as we felt ready to share him, Coronavirus hit! 🤦‍♀️
Happy Loving Day! 💙 Only 53 years ago the Supre Happy Loving Day! 💙 Only 53 years ago the Supreme Court struck down bans on interracial marriage. The case involved Mildred and Richard Loving who were arrested in Virginia for their interracial marriage. This case is a reason so many mixed-race families exist today. 💙 #lovingday #lovingday2020 📸: @fabiolacaravaphotography
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