There are so many reasons to be titillated with Chicago—stunning architecture, a vivacious music scene, and savory restaurants at every corner—however, every so often, we all need an escape. While there are many options for beautiful small towns in the vicinity of Chicago, distinctive historic ones stand out. Whether you want to meander down a secluded beach at sunset or peek into an antique shop for a treasured book, these small towns near Chicago will make you feel as if you have fallen straight into the scene of a Nicolas Sparks film.
1. Lake Forest, Illinois
While in Downtown Lake Forest, you can become lost while gazing at all the exquisite homes built along the water. The affluent neighborhood is situated along Lake Michigan and resonates an English countryside with its Tudor-style buildings and restaurants. Some popular places include Sweet’s, known for its ice cream, truffles, and chocolate, and the Deer Path Inn, styled after an English Manor Home and the quintessential place for afternoon tea.
📍: 30 miles north of Chicago
🕐: 1 hour
2. New Buffalo, Michigan
This nostalgic summer beach town is prominently understood as the Hamptons of the Midwest. New Buffalo has various beaches along the sandy, dune-packed Lake Michigan, making it the ideal getaway when you want a watersport adventure. When you’re not swimming along the shore, take in the sunset from the beach, assemble smores near a bonfire, or head into town and enjoy food from the local favorites such as Oinks Dutch Treats or The Stray Dog Bar and Grill.
📍: 70 miles northeast of Chicago
🕐: 1 hour and 30 minuites
3. St. Joseph, Michigan
St. Joseph is brimming with golden sand beaches, towering dunes, and restaurants that turn local ingredients into delicious meals with craft wines and beer. Eat at the Old Cabbage, a one-in-a-kind family-run restaurant that serves authentic German cuisine, or walk the Tiscornia Beach shoreline and capture the iconic red and white century-old lighthouse.
📍: 100 miles northeast of Chicago
🕐: 1 hour and 45 minuites
4. Long Grove, Illinois
One of our favorite small towns near Chicago, Long Grove is nestled within the cobbled-stone streets and lined with boutiques and dining options, such as Enzo and Lucia Ristorante and the Village Tavern. This quaint town has an annual Strawberry Fest, made up of three days of strawberry-infused food and drinks, carnival rides, and live music that lights up the usually quaint street.
📍: 24 miles north of Chicago
🕐: 1 hour
5. Galena, Illinois
The small town is a storybook setting with historic 1800s architecture that is dazzling as you stroll Main Street, coined “Helluva Half Mile,” which sprawls with more than 125 independently owned business shops. From a surfeit of dining options to wine tasting, it reverberates exuberance. Stop by Galena Sellers for a cozy and scenic vineyard and sip fermented red or white wine, or visit the Red’s Iron Yard & Wholesale Barn to find hidden gems and vintage pieces.
📍: 146 miles northwest of Chicago
🕐: 3 hours
6. Ottawa, Illinois
If you’re from Chicago, you’ve undoubtedly heard of Illinois’ most-visited national park: Starved Rock. It routinely draws in a surplus of outdoor enthusiasts and hiking newcomers because of its luscious waterfall and breathtaking trails. With spectacular views of Fox and Illinois rivers, it’s a little taste of the expansive Pacific Crest Trail while still only driving distance from Chicago.
📍: 90 miles east of Chicago
🕐: 1 hour and 45 minutes
7. Lake Geneva, Wisconsin
One of Chicagoans’ favorite small-town getaway destinations, notably the home of the Potawatomi Indians for eons, encompasses the entire lake and is sprinkled with Gilded Age mansions along the lakeside Shore Path. The charming tourist town offers a plethora of activities, from spa days to esteemed restaurants to dine at. You can even rent a scooter to make touring the downtown area a breeze.
📍: 75 miles northwest of Chicago
🕐: 2 hours
8. Chesterton, Indiana
Chesterton, a destination for the outdoor devotees, is located south of the Indiana Dunes National Park and the Indiana Dunes Park and boasts various trails if you’re in the mood for a strenuous hike or leisurely bike ride, all flooding from the beautiful beaches of Lake Michigan nearby. Wildlife enthusiasts can explore Coffee Creek Watershed Preserve, which includes the Chesterton Amphiteatre and Pavilion. Chesterton hosts a European Market every Saturday during the Summer.
📍: 50 miles southeast of Chicago
🕐: 1 hour