Chicago is a vibrant and exciting city, but sometimes you need to escape the hustle and bustle for a weekend getaway. Luckily, there are many amazing places to visit within a short drive of Chicago. Whether you’re looking for a charming small town, a stunning natural landscape, or a fun-filled city break, we have the perfect getaway for you.
15 Best Weekend Getaways from Chicago
Looking for the best weekend getaways from Chicago?
You’re in luck.
Sure, Chicago Illinois is one of the top travel destinations in the U.S., filled to the brim with amazing restaurants, great shopping, world-class museums and fun neighborhoods to explore. Sometimes, though, you need to step away from the excitement of the city and get away from it all.
Fortunately, Chicago’s proximity to the Great Lakes and the rolling hills of the Midwest means you don’t have to travel long distances from Chicago to escape into a relaxation paradise. There are tons of spots perfect for a weekend trip or day trips from Chicago that offer endless opportunities for outdoor activities and memory-making experiences year-round.
From taking long dune walks surrounded by the sounds of waves braking on the shore and kayaking along a gentle river, to exploring the small towns of Amish Country, you can easily find weekend getaways near Chicago to satisfy your need to escape.
Whether you’re looking for romantic getaway or a quick road trip from Chicago, we’ve rounded up some of the best destinations for you to explore.
Read on for my list of 15 favorite weekend getaways from Chicago, and be sure to scroll down for an interactive map to help you plan your getaway!
Weekend Getaways from Chicago in Indiana
Indiana Dunes
The Indiana Dunes National Park is an easy, quick getaway that will allow you to escape from the noise of the Windy City into a sandy oasis along the shore of Lake Michigan.
You’ll find 15 miles of Lake Michigan shoreline an hour from Chicago (traffic permitting). Here, you can immerse yourself in the beauty of the rugged dunes, pristine beaches, and lush forests as you embark on scenic hikes along the extensive network of trails. Capture the perfect Instagram-worthy shots at sunset from the iconic Mount Baldy or explore the diverse ecosystems of the Heron Rookery Trail.
Feel the sand between your toes at the world-renowned Indiana Dunes State Park and soak up the sun on the pristine beaches. Whether you’re a birdwatching enthusiast or a water sports lover, Lake Michigan offers endless opportunities for kayaking, swimming, and paddleboarding.
Be sure to make some memories at the charming lakeside villages offering local culinary delights and unique artisanal shops. Eat under twinkling lights on the patio of Ivy’s Bohemia House and Catering, or grab some picnic basket-ready treats and sandwiches from the Goblin and the Grocer and head for Indiana Dunes State Park.
PRO-TIP: Try a double scoop of Superman ice Cream at Valpo Velvet Ice Cream Shoppe, you’ll thank me later!
Fort Wayne Indiana
Located just three hours from the city, Fort Wayne makes a fun family getaway. You’ll love exploring the fascinating exhibits at the Fort Wayne Museum of Art. There’s a great collection of Midwest Impressionist paintings that capture the area’s stunning natural beauty that is a must-see.
Check out the city’s heritage at the History Center: if you plan your visit in late November, you can attend the “Festival of Gingerbread” and gawk at the amazing gingerbread creations.
There’s lot of family fun at the Fort Wayne Children’s Zoo, home to exotic animals and engaging activities, including the Australian House with dingo’s, kangaroos and black-tipped reef sharks! Be sue to stroll through the lush Foellinger-Freimann Botanical Conservatory or catch a captivating performance at the Embassy Theatre.
For a taste of local culture, explore the vibrant arts scene in the Arts United Center. Indulge in delectable dining options at local eateries like Baker Street Steakhouse (amazing prime rib) or try the amazing homemade pasta at Biaggi’s Ristorante Italiano. Finally, unwind with a scenic walk along the picturesque Rivergreenway, a scenic 26-mile linear park along the river.
South Bend Indiana
Explore the iconic University of Notre Dame campus, where architectural marvels meet collegiate charm. Even if you’re not a football fan, you can’t help but fall in town with this pure Midwest college town. Uncover the past at historical sites like the Studebaker National Museum and the Oliver Mansion, transporting you back in time.
For a scenic escape, meander along the serene paths of the Potawatomi Zoo or enjoy a leisurely stroll along the East Race Waterway. Indulge in culinary delights at local favorites like Café Navarre or LaSalle Grill, savoring the taste of the region’s flavors.
For a unique shopping experience, peruse the boutiques in the charming Eddy Street Commons or discover treasures at the South Bend Farmer’s Market.
Also Worth Checking Out: Turkey Run State Park, just under three hours south of Chicago. You can explore rugged canyons, scenic trails, and lush forests here. Gather up your courage and walk the iconic Suspension Bridge as you hike along the challenging trails that wind through stunning sandstone formations. Discover natural wonders at places like Rocky Hollow and enjoy the refreshing coolness of Sugar Creek.
Weekend Getaways from Chicago in Michigan
Harbor Country, Michigan
Just under two hours from Chicago, you’ll see so many Illinois license plates in Harbor Country that you’ll think you’re in a suburb of Chicago. It won’t take you long to discover why though.
This picturesque area in Southwest Michigan is the perfect retreat from the city. You’ll find eight communities (New Buffalo, Harbert, Sawyer, Three Oaks, Grand Beach, Michiana, Union Pier and Lakeside) each with their own unique appeal and flavor.
Head to the Lake Michigan beach town of New Buffalo to play in the lake, wander the bustling downtown and grab a sandwich at the Stray Dog. Kayak the Galien River and then head to Greenbush Brewing Company in Sawyer for a burger and Michigan craft beer. Grab a loaf of Swedish Limpa Bread at Luisa’s Swedish Bakery in Harbert (get their early, it sells out fast) before heading over to Three Oaks to do some serious antiquing.
St. Joseph Michigan
You’ve seen the picturesque lighthouse at the end of the pier on countless Instagram posts. There’s nothing like seeing it up close and personal, and you can do it in under two hours’ time from the Windy City.
Silver Beach, one of the best beaches in the world, is a hub of activity with everything from a sprawling splash pad and children’s museum to paddleboard rentals, concessions and hiking trails. Play beach volleyball or simply stretch out and relax on the sandy beach. St. Joe is located on the Lake Michigan Shore Wine Trail, and you can do a wine tour or visit the tasting rooms in the charming downtown shopping and dining area.
PRO-TIP: Fall is my favorite time to visit Michigan, when I can stroll the downtown streets all decked out in brightly-colored mums and pumpkins.
Grand Rapids Michigan
One of the biggest cities in Michigan, Grand Rapids can be reached in just over two hours from Chicago.
Whether you go for the amazing breweries (there’s more than seventy breweries here, earning it the name “BEER CITY”), the stunning parks or the walkable downtown, you’ll find lots to fill your weekend in Grand Rapids Michigan.
Head over Millenium Park and take in beauty along the endless miles of hiking and biking trails, and then make your way to the Downtown Market, a popular shopping and dining destination with a fresh fish market, a bakery, cheese shop, dine-in restaurants and so much more. Follow Lake Street East to Brewery Vivant, one of my favorite stops in the and continue to East Town. Wander the eclectic shops and restaurants and don’t miss Argo’s Comic and Used Book Store. The historic Amway Grand Hotel in downtown Grand Rapids or the Double Tree Inn on 28th Street are favorite places to stay here.
Use the Interactive Map of 15 Best Getaways from Chicago
Ann Arbor
South Bend isn’t the only Midwest College town worth visiting. You can Go Blue in Ann Arbor, just about a four-hour drive from the heart of Chicago.
The University of Michigan campus may be one of the quintessential college campuses in the country, and you’ll enjoy checking out the historic buildings of the Law Quad. There are some cool and unique museums here, like the Museum of Natural History, with its amazing planetarium.
Plan your trip right and catch a Big 10 football game at the Big House or visit in the winter and watch a basketball game. The U-M campus isn’t the only game in own, though.
Downtown Ann Arbor is home to kid-friendly spots like the Hands On Museum and the Michigan Firehouse Museum. You’ll also find some great restaurants, ranging from Krazy Jim’s Blimpy Burger to Cuban street food of Frida Baditos. Plan some time to kayak or hike along the picturesque Huron River as it winds through southeast Michigan, and stop by the Matthei Botanic Garden, a peaceful spot featuring nature trails and stunning garden spaces.
PRO-TIP: Be sure to check out mymichganbeach.com. Michigan’s top travel site for even more ideas for getaways from Chicago!
Weekend Trips from Chicago in Wisconsin
Lake Geneva Wisconsin
Just over 80 miles northwest of Chicago is the charming haven of Lake Geneva, Wisconsin. Long a summer getaway for Chicago residents, this pretty getaway is a picture-perfect spot to relax any time of the year. History buffs will love touring the Gilded Age mansions dotting the shoreline and wandering the old-fashioned Main Street at the Geneva Lake Museum. Delve into history at Black Point Estate and Gardens or find family fun at the Safari Lake Geneva.
Big Foot Beach State Park, set on five miles of Lake Geneva shoreline, offers a swimming beach, hiking trails and a sprawling family campground. Take in a fall festival or arts and crafts fair, for a truly Midwest experience. Sure, this is a perfect summer and fall getaway, but plan a visit in the winter, too. In the winter, Lake Geneva becomes a frozen fantasy of ice castles and caves lit with LED lights. Be sure to try the cheese curds and Wisconsin street corn at Lake City Social in the Cove Hotel, a popular family restaurant and bar.
PRO-TIP: The Grand Geneva Resort and Spa is a favorite place to stay here, with luxury guestrooms and villas. Play golf, swim in one of the pools or Lake Geneva or simply unwind at one of the on-site eateries overlooking the lake.
Elkhart Lake Wisconsin
This pretty, aqua blue lake is a pretty spot for anyone who loves outdoor activities like swimming, hiking, boating, or fishing. It’s easy to unwind here, nestled by the pristine waters, whether you’re kayaking, paddleboarding, or simply basking in the sun on the sandy shores.
Discover history at the Road America Racetrack or indulge in a leisurely stroll through the Osthoff Resort’s Gardens. Culinary delights await at Lake Street Café or Paddock Club, where local flavors take center stage. For shopping, meander through the boutique shops downtown, where you can find artisan crafts, souvenirs, and more.
Elkhart Lake promises an unforgettable weekend escape with a blend of natural beauty, exquisite dining, and delightful shopping.
Madison Wisconsin
Located just two and a half hours from Chicago, Madison might be my favorite spot in Wisconsin.
There’s so much to do in the college town (the University of Wisconsin is here) sandwiched between two lakes, Lake Mendota and Lake Monona. Surrounded by endless parks and beaches, outdoors enthusiasts can swim, boat, hike, and bike around the city, or simply take a sunset cruise to enjoy the picturesque surroundings.
This is the heart of Wisconsin’s cultural area, and you’ll find two free art museums, including the Madison Museum of Contemporary Art, as well as many other fun museums that the kids will love (we’re looking at you, National Mustard Museum). Olbrich Botanical Gardens, home to an authentic Thai Garden is fun to visit any time of the year, and the Dane County Farmers Market is one of the best farm markets in the Midwest.
Take a tour of Frank Lloyd Wright’s First Unitarian Meeting House, an architectural masterpiece listed as a National Historic Landmark. A Wisconsin native, Frank Lloyd Wright lived in Madison at one point and you’ll see several of his designed throughout the city.
Milwaukee Wisconsin
Just over an hour north of Chicago is a treasure trove of activities for all ages. Immerse yourself in the city’s rich history with visits to the Milwaukee Public Museum and the Harley-Davidson Museum. For a family-friendly adventure, explore the Milwaukee County Zoo, where exotic animals await.
Stroll along the RiverWalk and enjoy the scenic views of the Milwaukee River. Indulge your taste buds at acclaimed eateries like The SafeHouse or Sobelman’s Pub & Grill, offering a true taste of the city’s culinary scene. Discover unique finds while shopping in the Historic Third Ward, home to boutiques, galleries, and artisanal shops.
Don’t miss out on sipping local brews at breweries like Lakefront Brewery or Milwaukee Ale House. With a blend of cultural experiences, kid-friendly attractions, dining delights, and shopping opportunities, you’re sure to have fun here.
Be sure to check out the Bay View shopping area, home to URSA, a lifestyle and pant shop which has been featured in Vogue as on of the best shopping experiences in the US.
Also Worth Checking Out in Wisconsin
Door County Wisconsin
Located about 300 miles north of Chicago is Door County, set on a rugged peninsula jutting out into Lake Michigan and Green Bay. There’s beautiful coastline to explore with tiny towns tucked away along the shoreline.
Fresh fish and cherries in the summer make it a must-visit spot. Stay in a log cabin or cozy bed and breakfast, and wake to the sounds of the waves landing on the rocky shore. The American Club in Kohler WI is a must-visit here.
Off the Beaten Path: If you really want to get away, head to Vilas County for hiking, biking, boating, swimming and more.
Weekend Getaways from Chicago in Illinois
Galena Illinois
This historic gem of a city near the Mississippi Rivers towering bluffs offers a perfect blend of charm and relaxation. Explore the cobblestone streets and marvel at the beautifully preserved 19th-century architecture. Discover the rich history at Ulysses S. Grant Home or explore the depths of the Dowling House.
Meander through boutique shops in the Main Street shopping district, where you’ll find unique antiques and local crafts. When it’s time to dine, indulge in local flavors at culinary gems like Fried Green Tomatoes or One Eleven Main. With its historic allure, delightful shopping, and savory dining options, Galena IL promises a rejuvenating weekend getaway.
Starved Rock State Park
Immerse yourself in the breathtaking landscapes of Starved Rock State Park, where majestic canyons, cascading waterfalls, and lush forests await your exploration. Embark on scenic hikes along the well-maintained trails and capture stunning vistas from Lover’s Leap Overlook. Unwind with a leisurely paddleboat cruise along the Illinois River, or indulge in birdwatching along the park’s diverse ecosystem. After a day of adventure, satisfy your cravings at the historic Starved Rock Lodge’s dining room, offering delectable local cuisine.
Discover the rich history of the region at the Rock Ridge Quarry and Kilgore Falls. After a day of exploration, satisfy your appetite at local dining spots like Falling Branch Brewery or Jarrettsville Creamery & Deli, where local flavors abound. For shopping, peruse the unique artisanal shops for souvenirs and handmade crafts. With a blend of natural beauty, savory dining, and charming shopping, Starved Rock is your perfect weekend escape.
Shawnee National Forest
Located just over 325 miles southwest of Chicago in Herod, IL, Shawnee National Forest is a true respite from the hustle and bustle of city life.
From the awe-inspiring Garden of the Gods’ rock formations to the serene beauty of the Little Grand Canyon, you’ll be amazed at the natural beauty of this area near the Mississippi River. Hike along the scenic trails of Rim Rock, and don’t miss the panoramic views from Inspiration Point.
For retail therapy, explore charming shops in nearby towns like Carbondale or Murphysboro, offering unique crafts and souvenirs. When hunger strikes, savor local flavors at restaurants such as Giant City Lodge or Yellow Moon Café. With its diverse landscapes, quaint shopping, and delectable dining, Shawnee National Forest promises an unforgettable weekend retreat.
Rockford Illinois
Explore the mesmerizing Anderson Japanese Gardens, a haven of tranquility and beauty. Discover history at the Burpee Museum of Natural History and embrace creativity at the Rockford Art Museum. For outdoor enthusiasts, the Rock Cut State Park offers hiking trails and serene lakes, perfect for boating and picnicking.
Savor the local flavors at dining hotspots like Abreo Restaurant or Octane InterLounge, offering a culinary journey through the region. When it comes to shopping, the boutiques of the historic Prairie Street Brewhouse or the CherryVale Mall promise delightful finds. With a fusion of exploration, delectable dining, and retail therapy, Rockford guarantees an unforgettable weekend escape.
Fox River Valley
Embark on relaxing boat cruises, paddleboarding adventures, or simply enjoy a leisurely stroll along the riverbanks. Explore the rich history at local landmarks like the Fabyan Villa Museum and Japanese Garden or the Batavia Depot Museum.
For a culinary journey, delight your taste buds at dining gems like The Office or Water Street Tavern, where local flavors shine. When it comes to shopping, the boutiques and galleries in charming riverside towns provide unique finds and keepsakes. With a mix of natural splendor, delectable dining, and delightful shopping, Fox River promises an unforgettable weekend escape. You’ll forget you’re just an hour west of Chicago busy streets.
EXPERT TIP: if youl’re looking for some great winter getaways, check out this post on the Best Skiing Near Chicago.