top Road Trips From Chicago for Cars

Why Take a Road Trip From Chicago?

Sometimes you just need to escape the hum of the city and the endless stoplights. Whether you’re craving wide-open roads, small-town charm, or lakeside serenity, road trips from Chicago by car offer the perfect mix of adventure and freedom. And the best part? You don’t have to travel far to find unforgettable destinations.

There’s something uniquely rewarding about hopping in your car, playlist queued, snacks in reach, and the whole day stretching ahead. From scenic byways to peaceful countryside, the Midwest packs plenty of beauty within a few hours’ drive from the city.

Here’s why hitting the road from Chicago is a fantastic idea:

• Total freedom: No TSA lines, no train schedules—just you, your car, and the open road.
  
• Variety in every direction: Drive north for lakes and lighthouses, south for history and food, or west for natural wonders.
  
• Perfect for weekend getaways: Many destinations are 2–4 hours away—ideal for a quick reset.
  
• Cost-effective travel: With gas prices often lower than plane tickets, road trips can be budget-friendly too.
  

So whether you’re solo cruising with your favorite podcast or packed in with the family for a weekend getaway, the road from Chicago is always calling.

What to Know Before You Hit the Road

Before you put the pedal to the metal, it pays to plan a little. A smooth road trip starts with smart prep—especially when you’re relying on your car to carry you the distance. Here’s what you need to know:

1. Prep Your Car Like a Pro

Make sure your vehicle is road-ready to avoid any surprises mid-journey:

•  Check tire pressure and tread depth
  
•  Top off fluids: oil, coolant, windshield washer
  
•  Test your brakes and lights
  
•  Ensure your spare tire and jack are in good condition
  

Consider getting a quick tune-up if it’s been a while. Peace of mind is worth it.

2. Pack Smart (and Light)

You don’t need to bring the whole house. Just focus on the essentials:

• Snacks and water (because no one likes a “hangry” co-pilot)
  
• Phone chargers and backup power banks
  
• Printed directions or offline maps (cell signals can fade in rural areas)
  
• Comfort items: travel pillows, sunglasses, hand sanitizer, wet wipes
  

3. Use Apps That Make Driving Easier

These tools can turn a good road trip into a great one:

• Google Maps or Waze for smart navigation
  
• GasBuddy to find cheap fuel stops
  
• Roadtrippers to discover quirky roadside attractions
  
• Spotify or Audible to keep boredom at bay
  

4. Budget for the Unexpected

From tolls on I-90 to surprise detours, keep a little wiggle room in your budget. Carry some cash for rural stops that may not take cards.

Starting your journey with the right mindset and preparation means less stress and more joy on the road. Whether you’re planning a spontaneous day trip or a full weekend escape, setting yourself (and your car) up for success makes all the difference.

Ready to explore? Let’s dive into the best scenic road trips from Chicago next.

Top Scenic Road Trips From Chicago (Under 3 Hours)

Looking for a quick escape that feels worlds away from city life? You’re in luck. Chicago is perfectly positioned for some of the best short-distance road trips in the Midwest. Within just a few hours’ drive, you’ll find peaceful beaches, lush forests, and charming small towns—all perfect for a day trip or overnight stay.

These routes are not just close—they’re scenic, car-friendly, and packed with things to see along the way. Let’s hit the road!

 1. Indiana Dunes National Park, Indiana

Drive time: ~1 hour
Why go: If you’re craving beach vibes without the flight, this is your go-to.

• Explore 15+ miles of Lake Michigan shoreline
  
• Hike towering sand dunes and forest trails
  
• Spot wildlife at the Great Marsh Trail
  
• Perfect for: beach lovers, photographers, and families
  

Insider Tip: Visit during sunrise or sunset for breathtaking lake views with fewer crowds.

 2. Lake Geneva, Wisconsin

Drive time: ~1.5 hours
Why go: This lakeside resort town oozes charm and relaxation.

• Stroll the scenic Shore Path that circles the lake
  
• Rent a boat or take a guided cruise
  
• Shop and dine in the quaint downtown area
  
• Perfect for: romantic getaways and spa weekends
  

Pro tip: Book a lakeside Airbnb in advance during summer—it gets busy fast.

 3. Starved Rock State Park, Illinois

Drive time: ~1.75 hours
Why go: Nature lovers, this one’s for you. Starved Rock offers dramatic canyons and seasonal waterfalls just a short drive away.

• Hike over 13 miles of trails through sandstone bluffs
  
• Catch stunning views from Lover’s Leap Overlook
  
• Ideal picnic spots and scenic drives nearby
  
• Perfect for: hikers, families, and fall foliage chasers
  

Don’t miss: Matthiessen State Park, just a few miles south—it’s a hidden gem with fewer crowds.

 4. New Buffalo, Michigan

Drive time: ~1.5 hours
Why go: This Lake Michigan gem blends small-town charm with upscale vibes.

• Relax on the sandy New Buffalo Public Beach
  
• Tour local wineries along the Lake Michigan Shore Wine Trail
  
• Enjoy fresh seafood at harborfront restaurants
  
• Perfect for: couples, wine lovers, and foodies
  

Road note: The I-94 stretch can get congested—leave early for a smoother ride.

These short road trips from Chicago are proof that you don’t need a full tank of gas or a week off to recharge. With scenic drives, memorable stops, and plenty of photo ops along the way, each destination offers its own flavor of escape.

Best Weekend Getaways From Chicago by Car

If you’re ready to trade your skyline view for something a little more scenic—but still want to keep it under a half-day’s drive—weekend road trips from Chicago are the way to go. These destinations let you unwind, explore, and recharge, all without needing a flight or extensive planning. They’re perfect for couples, families, or solo travelers looking to break the routine.

Here are some tried-and-true weekend getaways that are just a car ride away:

 1. Galena, Illinois

Drive time: ~3 hours
Why go: This historic town is like stepping into a postcard.

• Explore 19th-century architecture and cobblestone streets
  
• Visit Ulysses S. Grant’s home and other historic landmarks
  
• Shop local boutiques and enjoy cozy wine bars
  
• Perfect for: history buffs and antique lovers
  

Tip: Galena’s Main Street is especially charming in the fall and around the holidays.

 2. Milwaukee, Wisconsin

Drive time: ~1.5 hours
Why go: Don’t sleep on Milwaukee—it’s packed with energy, culture, and lakeside beauty.

• Tour Lakefront Brewery or check out the Harley-Davidson Museum
  
• Walk along the Riverwalk and explore the Public Market
  
• Catch a show or concert at one of the city’s many venues
  
• Perfect for: beer enthusiasts, art lovers, and urban explorers
  

Road tip: Take I-94 for a smooth, direct drive—but avoid rush hour traffic leaving Chicago.

 3. Holland, Michigan

Drive time: ~2.5 hours
Why go: Windmills, tulips, and a lovely beach—Holland offers a unique blend of Dutch heritage and Michigan charm.

• Visit the Windmill Island Gardens and Dutch Village
  
• Enjoy Holland State Park Beach on Lake Michigan
  
• Try authentic Dutch pastries downtown
  
• Perfect for: springtime escapes, family fun, and nature lovers
  

Best time to visit: Late April to early May during the Tulip Time Festival.

 4. Madison, Wisconsin

Drive time: ~2.5 hours
Why go: Wisconsin’s capital has a vibrant college-town feel paired with beautiful natural scenery.

• Stroll through the University of Wisconsin Arboretum
  
• Dine and shop around State Street
  
• Kayak or paddleboard on Lake Mendota
  
• Perfect for: active weekends, foodies, and first-time road trippers
  

Bonus: The drive through southern Wisconsin is full of rolling hills and photo-worthy farmland.

These destinations prove that a weekend is all you need to hit reset. Whether it’s lakeside views, boutique shopping, or delicious local eats, each of these car-friendly road trips from Chicago delivers memorable moments—no plane ticket required.

Longer Road Trip Routes Worth the Drive (4+ Hours)

Sometimes, the best road trips from Chicago are the ones that take you a bit farther. These longer drives are perfect if you have a long weekend or want to soak in more dramatic scenery and deeper adventures. Trust us—these are worth every mile.

 1. Door County, Wisconsin

Drive time: ~4.5 hours
Why go: Dubbed the “Cape Cod of the Midwest,” this peninsula offers coastal charm, cherry orchards, and art galleries.

• Visit Fish Creek and Ephraim for adorable small-town vibes
  
• Tour lighthouses and explore Peninsula State Park
  
• Enjoy wine tasting and cherry pie along the coast
  
• Perfect for: romantic weekends and family-friendly getaways
  

Road tip: Take the scenic drive up Highway 42—it’s beautiful in every season.

2. Route 66 (Illinois Stretch)

Drive time: Varies based on how far you go
Why go: Take a nostalgic journey along America’s most iconic road.

• Start in Chicago and head southwest toward Pontiac, IL
  
• Visit classic diners, old-school gas stations, and roadside murals
  
• Explore the Route 66 Hall of Fame Museum
  
• Perfect for: history lovers and vintage road trip fans
  

Fun idea: Create a playlist of retro hits and cruise with the windows down.

 3. Michigan’s Gold Coast (Saugatuck to Traverse City)

Drive time: ~3.5 to 6 hours depending on how far north you go
Why go: Gorgeous beaches, wineries, and dunes define this stunning stretch of Lake Michigan shoreline.

• Hike the Sleeping Bear Dunes National Lakeshore
  
• Relax in Saugatuck or Grand Haven for artsy beach town vibes
  
• Tour vineyards near Traverse City
  
• Perfect for: nature lovers, wine drinkers, and summer adventurers
  

Pro tip: This is an ideal summer or early fall trip—book lodging early during peak seasons.

These extended road trips allow you to lean into the joy of the journey. With a little more time and a full tank of gas, you can uncover parts of the Midwest that feel like whole new worlds.

Car Travel Tips for Smooth and Safe Journeys

You’ve got the route, the snacks, and the destination—but don’t forget the details that make a road trip smoother. Whether you’re heading out for a couple of hours or a weekend away, these car travel tips will help you cruise with confidence.

 1. Pre-Trip Car Check

Give your car a once-over before you head out:

• Inspect tire pressure and tread
  
• Check oil and fluid levels
  
• Make sure headlights and signals are working
  
• Pack a spare tire, jack, and jumper cables
  

 2. Navigation and Route Planning

• Use Google Maps or Waze for real-time updates
  
• Download offline maps in case you lose signal
  
• Plan rest stops every 2–3 hours to stretch and refuel
  

 3. Pack Like a Road Warrior

Essentials to keep in your car:

• Chargers and cables
  
• Reusable water bottles and snacks
  
• First aid kit and hand sanitizer
  
• Sunglasses and sunscreen
  
• Travel pillow or blanket for naps on the go
  

 4. Apps That Make Travel Easier

• GasBuddy for locating cheap fuel
  
• Roadtrippers to find attractions along your route
  
• Spotify or Audible for entertainment
  
• HotelTonight for last-minute bookings
  

 5. Stay Flexible and Enjoy the Ride

Traffic jams, closed trails, or weather hiccups? It happens. The key to a great road trip is embracing the unexpected and staying relaxed

With a little preparation and the right mindset, your road trip from Chicago can go from good to unforgettable.

Seasonal Road Trips From Chicago: Where to Go & When

One of the best things about road tripping from Chicago is that every season brings its own kind of magic. Whether you’re chasing fall colors, spring blossoms, summer sunshine, or snow-dusted towns, there’s always somewhere worth driving to. Choosing your destination based on the season not only enhances the experience but also helps you avoid crowds and align with local events.

Here’s a breakdown of the best seasonal road trips to consider from Chicago:

 Fall – Starved Rock & Galena, IL

• Why: Fall foliage in the Midwest is breathtaking, and these spots offer some of the most vibrant leaf displays.
  
• Activities:
  
  • Hike through colorful canyons at Starved Rock
    
  • Take a scenic drive along Route 20 to Galena
    
  • Visit local harvest festivals and farmers markets
    
• Car tip: Pack layers and keep a cozy blanket in your trunk for chilly evenings.
  

 Spring – Holland, MI & Indiana Dunes

• Why: Flowers are in bloom, and lake towns start coming alive without the summer crowds.
  
• Activities:
  
  • Attend the Tulip Time Festival in Holland
    
  • Walk the blooming trails of Indiana Dunes
    
  • Spot migrating birds in the marshlands
    
• Pro tip: Spring showers are common, so keep an umbrella handy in your backseat.
  

 Summer – New Buffalo, WI & Door County, WI

• Why: Lake Michigan shines in summer, and beach towns are at their best.
  
• Activities:
  
  • Hit the beach and enjoy watersports
    
  • Visit farmers markets, wineries, and festivals
    
  • Enjoy outdoor dining and sunset picnics
    
• Navigation tip: Leave early on weekends to avoid heavy outbound traffic.
  

 Winter – Lake Geneva, WI & Milwaukee, WI

• Why: These cozy towns offer charming winter vibes, holiday lights, and indoor attractions.
  
• Activities:
  
  • Ice skate, shop, and sip hot cocoa
    
  • Explore museums and art galleries
    
  • Stay at a lakeside resort for a relaxing snowy retreat
    
• Winter reminder: Keep a winter emergency kit in your car—think blanket, flashlight, and scraper.
  

By aligning your road trips with the seasons, you’ll not only enjoy better weather and scenery—you’ll also get the most out of each destination’s unique offerings.

Final Thoughts: Make Your Road Trip Memorable

There’s something incredibly freeing about the open road—especially when it starts just outside your doorstep in Chicago. Whether you’re exploring lake towns, hiking forest trails, or chasing fall foliage, road trips from Chicago for cars offer the perfect blend of accessibility and adventure.

To wrap things up, here are a few parting tips to help you craft the perfect journey:

 Quick Recap Checklist:

• Choose your destination based on distance and season
  
• Prep your car for safety and comfort
  
• Use travel apps to enhance your experience
  
• Pack light but don’t forget the essentials
  
• Stay flexible and leave room for spontaneous detours