There are so many reasons to be titillated with Chicago—stunning architecture, a vivacious live music scene, and savory new 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.
📍Distance from Chicago: 30 miles north of Chicago
🕐 Time from 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.
📍Distance from Chicago: 70 miles northeast of Chicago
🕐 Time from Chicago: 1 hour and 30 minutes
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 On The River Tavern, a one-in-a-kind riverside pub that serves authentic American food and craft beer, or walk the Tiscornia Beach shoreline and capture the iconic red and white century-old lighthouse.
📍Distance from Chicago: 100 miles northeast of Chicago
🕐 Time from Chicago: 1 hour and 45 minutes
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.
📍Distance from Chicago: 24 miles north of Chicago
🕐 Time from 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.
📍Distance from Chicago: 146 miles northwest of Chicago
🕐 Time from 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.
📍Distance from Chicago: 90 miles east of Chicago
🕐 Time from 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.
📍Distance from Chicago: 75 miles northwest of Chicago
🕐 Time from Chicago: 2 hours
8. Chesterton, Indiana
Chesterton, a destination for 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.
📍Distance from Chicago: 50 miles southeast of Chicago
🕐 Time from Chicago: 1 hour
9. Geneva, Illinois
It is one of the charming towns near Chicago that reminds you of Star Hollow from Gilmore Girls—on a smaller scale. With over 160 specialty shops and restaurants, downtown historic Geneva is one of the best shopping and dining experiences with infinite choices, from the refurbished downtown storefronts to the dozens of treasured Third Street Victorian homes that now house over 100 unique specialty shops and quaint eateries.
📍Distance from Chicago: 45 miles southwest of Chicago
🕐 Time from Chicago: 1 hr 30 min
10. Evanston, Illinois
The home of Northwestern University, Evanston, is a beautiful small town with a gorgeous city center filled with palatable restaurants, stores, and live music venues. It’s also blocks from Lake Michigan, so you get the combination of vibrant city life with the tranquility of lakeside living. It’s a beautiful town near Chicago to spend the day at, so we highly recommend it.
📍Distance from Chicago: 20 miles
🕐 Time from Chicago: 1 hr