Whether you’re after romantic things like a riverside stroll or eager to explore new Midwest towns, there’s a list of Chicago getaways, just a few hours away that promises new adventures. Living in or around the Windy City offers more than just skyline views and bustling downtown energy, it opens the door to a variety of long weekend escapes perfect for every kind of traveller. Check out the best road trips from Chicago, blending lakefront charm, artsy small towns, and scenic trails all within driving distance from the Chicago River.
Wandering Through Galena’s Timeless Streets in the Heart of Fall
Located about 160 miles west of Chicago, Galena is one of Illinois’ favorite road trips. With its main streets lined by 19th-century architecture and boutique tea houses, this town charms with its nods to history and creativity. Galena is great for couples seeking romantic things to do, from long walks through town to cozy evenings at hotels like Eagle Ridge Resort.Take a day date through the historic district, explore the Marshall Fields building, and don’t miss the town’s quaint museum exhibits or guided ghost tours. Fall is the best time to visit, especially during the perfect fall road trip season when colourful leaves add magic to the cobblestone streets.
Saugatuck Feels Like Midwest’s Best Kept Creative Escape
Just over three hours from Lake Shore Drive, Saugatuck is the kind of place that blends culture with beachy fun. Bordered by Lake Michigan, this artsy town offers everything from contemporary art galleries and quaint home decor shops to long days at Oval Beach, which ranks high among the best spots for a summer dip or picnic.
Take a thrilling dune ride, visit the art galleries, and enjoy a long meal at The Southerner, a local favourite. The main strip is perfect for slow strolls and window shopping. If you’re visiting in fall, Saugatuck transforms into a harvest haven with pumpkin patches, cider houses, and rustic colour splashed views, ideal for your fall road trip Chicago getaways.
Rockford a Surprisingly Fun and Quirky Weekend Pick
A short two-hour drive northwest of the city brings you to Rockford, home to the Midway Village Living History Museum and one of the region’s largest sock monkey collections. Yes, really. The city offers a mix of museum museums, like the Burpee Museum of Natural History, perfect for families or curious adults. Rockford also boasts Anderson Japanese Gardens, one of the most serene places in the state.
Head downtown for live music, good eats, and great coffee at Trolley Depot Coffee. If you’re traveling with older kids, this is a super cool place for low-key fun. Try the local Swedish bakery for pastries and take home quirky gifts like hand-sewn sock monkeys.
Milwaukee Surprise with Culture, Beer, and Big Lake Energy
Milwaukee is less than 90 minutes from Chicago and brings a completely different city vibe to the table. Known for its vibrant lakefront brewery scene and cultural landmarks, it’s a luxury trip that doesn’t break the bank. Stroll the museum campus, including the Milwaukee Art Museum, or explore the waterfront via bike or river cruise.
Foodies will love original Gino’s East for pizza and nice rooftop bars like Café Benelux. Don’t miss Massive rooftop bars for sunsets and city views that rival any observation deck Chicago can offer. It’s also a top pick for long walks along the harbour, making it one of the most scenic new Midwest towns to explore during summer or fall.
Tasting, Shopping, and Relaxing Through Harbor Country
Just under three hours away, Harbor Country featuring New Buffalo, Three Oaks, and Sawyer is a cluster of coastal charm. Known for its main strip of antique stores, tea rooms, and scenic beaches, it’s a standout among favorite cities for those who love wine, wellness, and wandering.
Start your trip at Journeyman Distillery, swing by sock monkey shops and head to the beach for kayaking or watching sunsets over Lake Michigan. If you’re in the mood for shopping, explore local boutiques filled with home decor finds and artisan pieces. The best time to visit is late summer to early fall, when the air is crisp and the crowds start thinning.
Visit Starved Rock When You’re Craving a Nature Reset
Located two hours southwest of the Windy City, Starved Rock delivers jaw-dropping canyon views, especially in spring and autumn. It’s home to scenic trails, waterfalls, and overlooks, perfect for hiking or photography. Nearby Matthiessen State Park also draws visitors with similar rugged beauty minus the crowds.
Take a guided hike or try luxury glamping at Camp Aramoni, where long meals are served under the stars. After your trek, visit The Lone Buffalo for hearty eats and local brews. This Chicago getaways spot also features live music on weekends and a large outdoor patio perfect for cool-weather evenings.
Indiana Dunes is Closer And Totally Worth It
If you need a last-minute getaway, Indiana Dunes National and State Park is less than an hour from Chicago. With hiking trails, sandy beaches, and woodland preserves, it’s a compact escape packed with nature. Whether you’re tackling the 3 Dune Challenge or snapping Instagram shots along the lake shore, this trip has something for everyone.
Pop into nearby Chesterton or Valparaiso for food and tea houses, or plan a Monday morning retreat when the beaches are quiet and peaceful. It’s a good spot for couples, solo travellers, or families who need to disconnect and recharge.
Stick Around Chicago for a Local Getaway
Don’t underestimate Chicago itself when it comes to unforgettable getaways. Whether you’re a local planning a day date or a visitor spending a long weekend downtown, the city has no shortage of magic. Stroll through Millennium Park and snap a photo at the famous Cloud Gate sculpture. Take river cruises along the Chicago River to learn more about Chicago’s architectural history.
Explore the Art Institute, Field Museum, or 360 Chicago at the John Hancock Center for those unbeatable observation deck level views. Observation decks like the Skydeck or LondonHouse Chicago’s massive rooftop bar give you front-row seats to sunset over the skyline. Grab brunch on the LondonHouse Hotel terrace or explore the dazzling Tiffany Dome inside the Chicago Cultural Centre.
The museum campus alone offers days of discovery, especially if you’re exploring with family. Whether you love art, natural history, or photography, this blog post is your sign to rediscover the city and its most romantic corners.
Let These Chicago Getaways Kickstart Your Next Adventure
Whether you’re soaking up skyline views from a tall tower, chasing waterfalls at Starved Rock, or digging into deep dishes in New Buffalo, these favourite road trips from Chicago are packed with new flavours, scenic backdrops, and fresh perspectives. From nice rooftop bars to small-town art walks, there’s no shortage of super cool places waiting to be explored.
Now’s the time to pack your bags, grab your road trip playlist, and create your next unforgettable weekend memory.