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A street with parked cars and small brick and wood buildings. The main street has shops, a wide sidewalk, and street lamps.
Downtown of Galena, Illinois
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18 small towns near Chicago you need to visit right now

Hit the road and escape for a weekend to these Midwest towns

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Downtown of Galena, Illinois
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With a population close to 3 million, the hum and hustle of Chicago can be invigorating—until it’s not. When the traffic and noise get to be too much, it’s comforting to know that there are quaint small towns, prairie landscapes, and state parks that are just a short drive away. Whatever you’re after, we’ve got you covered with these equal parts charming and captivating Midwestern towns.

Perhaps you’re longing for a weekend on a scenic lake or a tour of architectural marvels and historic buildings? Maybe you need to soak up some nature on a calm, beautiful hiking trail? So, hit the road and explore these 18 towns. Escape for the day or take the whole weekend. The Midwest is yours.

Map points are arranged generally by shortest to longest distance from Chicago.

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1. Chesterton

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Situated directly alongside Indiana Dunes State Park, Chesterton has no shortage of natural beauty. The waves of Lake Michigan will have you believing that you’ve been transported to the seaside, along with sandy dunes that can reach a height of over 200 feet. Charming inns and local diners abound.

2. Dundee

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The Fox River runs all the way through this small, 6-square-mile town. Of course, there’s all the hiking, biking, and camping in forest preserves near the river. But, if you really need a change of scenery, Santa’s Village Azoosment Park is a kitschy Christmas-themed attraction with carnival rides and a petting zoo (it’s open May through October).

3. Fox Lake

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Part of the Chain O’ Lakes region, Fox Lake is a great waterfront getaway. Fishing enthusiasts and outdoorsy folks will love that the harbors and marinas with boat rentals all around the lake. If your up for trying something more active, Wilmot Mountain is just 15 minutes north. In the summer, it’s the site of obstacle courses and other athletic events. Come winter, the hills are filled with snow bunnies learning to ski.

4. Woodstock

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Although its claim to fame lies in a little Bill Murray film called Groundhog Day, Woodstock’s idyllic small-town scenery has other charms such as the brick streets and old buildings. The town square is on the National Register of Historic Places and features a historic opera house built in 1889 with Carpenter Gothic and Moorish influences.

5. New Buffalo

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Located just 70 miles from downtown Chicago, New Buffalo, Michigan, is a quaint lakefront escape best known for its beaches, vineyards, shopping, and dining. Explore downtown on your own or sign up for a tour of the area’s many wine tasting rooms and distilleries. For nature-lovers, nearby Galien River County Park is a great waterfront hiking spot.

6. Lake Geneva

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A favorite getaway among Chicagoans, Lake Geneva is a small town with stately mansions. The 26-mile Shore Path, previously used for thousands of years by Native American tribes, circles the entire lake, and it’s the perfect opportunity to see the area’s storied mansions up-close. Don’t miss Stone Manor, the largest historic home on the lake, and the Wrigley Estates, a collection of properties built by the chewing gum king.

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7. Ottawa

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Ottawa is only 15 minutes away from Illinois’ most popular natural area: Starved Rock State Park. Drawing in travelers with its waterfall and stunning hiking trails, Ottawa has its own eye-catching views, resting along both the Fox and Illinois rivers. The town center, Washington Square, is a historic district anchored by the Reddick Mansion. The Italianate home is one of the largest and most ornate residences built in the mid-1800s in the Midwest.

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8. St. Joseph

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St. Joe’s tag line? The Riviera of the Midwest. See sand dunes along the lakeshore and later on, explore the countryside’s orchards and vineyards. The picture-perfect lighthouse at the end of a long pier is one of the most scenic places. But, it’s worth it to check out the downtown shopping district, the shoreline on Silver Beach, and the views from Lake Bluff Park.

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9. Winamac

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This Indiana town is really all about its location along the Tippecanoe River. In fact, the name Winamac comes from the native Algonquian word for “Catfish.” Head to Tippecanoe River State Park for camping, kayak rentals, hiking trails, bike paths, and birding areas. Be sure to climb to the top of the Fire Tower for unparalleled tree-top vistas.

10. Fort Atkinson

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Nestled along the Rock River, Fort Atkinson got its start in 1832 as, you guessed it, a military fort. Nowadays, there’s plenty of entertainment to go around with a vibrant community theater scene, music festivals, and the celebrated Fireside Theatre, marked by its can’t-miss-it, blaze-orange sculpture designed in 1970 by a local art teacher. Cyclists should check out the sculpture-lined Glacial River Bike Trail.

11. Cedarburg

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Going to Cedarburg can feel a lot like stepping out of a time machine. The limestone buildings, preserved since the 1840s, now act as destinations for meandering tourists with shops, artists’ studios, restaurants, and an award-winning winery. The town’s covered bridge, built in 1876, is one of the last remaining examples in the entire state. The retired structure was made from local pine trees and milled 100 miles away in Baraboo.

12. Fulton

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In Fulton, take a self-guided tour through Heritage Canyon, a forested area that spotlights 19th-century structures like the Canyon Church, blacksmith shop, and schoolhouse. And with its Dutch heritage, it’s only natural that this town has a bucolic windmill, originally manufactured in the Netherlands.

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13. Kohler

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The village of Kohler is the epitome of Midwestern charm. The five-star resort The American Club, rooted in its beginnings in 1918 as a home to European immigrant workers, is no stranger to twinkling lights and horse-drawn carriage rides. Here, you can relax with therapeutic water treatments at the Kohler Waters Spa or take a factory tour to see how the company makes vitreous china sinks and 6-foot cast iron tubs.

14. New Glarus

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The fingerprints of New Glarus’ Swiss settlers can still be witnessed today through the town’s buildings and murals—many of them look as if they’ve been plucked from the Alps. When you visit sample cheese curds and the local ale at New Glarus Brewing. The brewery sits on a hilltop and the outdoor patio is clad in limestone steps with a remnants of what very well could be a European castle.

15. Elkhart Lake

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About an hour north of Milwaukee, there’s a lakeside locale that’s both peaceful—tall cedars, gentle waves lapping at the shore—as well as heart-pounding. Home to Road America racetrack, Elkhart Lake’s road-racing history began back in the 1950s on its public roads. Visitors can still cruise the original street circuit with historical markers along the way.

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16. Galena

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The picturesque town is sure to recharge. More than three-quarters of Galena’s buildings are listed in the National Register of Historic Places. There’s an abundance of 1800’s architecture to admire as you amble along the town’s illustrious Main Street, coined “Helluva Half Mile” and brimming with delightful antique shops and restaurants. Don’t miss the Aldrich Guest House—a bed and breakfast set in an 1845 Greek Revival mansion.

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17. Spring Green

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Spring Green is your typical Wisconsin town, except for the local attractions. People are often surprised to learn that Frank Lloyd Wright’s home Taliesin resides in this quiet community. Down the road, you’ll find The House on the Rock, an architectural wonder built by Alex Jordan in 1945 to showcase his quirky collections. Also, be sure to take in a Shakespearean performance at the renowned American Players Theatre.

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18. Quincy

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Quincy is the furthest destination on our list but is worth the trip. The town is an architecture aficionado’s wonderland and features thousands of buildings in four National Historic Register Districts. Some are homes were constructed before the Civil War with distinct European influences, while others echo Frank Lloyd Wright’s Prairie style designs. Take a self-guided architecture driving tour or follow a guide to explore the area’s private homes.

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1. Chesterton

Chesterton, IN 46304

Situated directly alongside Indiana Dunes State Park, Chesterton has no shortage of natural beauty. The waves of Lake Michigan will have you believing that you’ve been transported to the seaside, along with sandy dunes that can reach a height of over 200 feet. Charming inns and local diners abound.

2. Dundee

Dundee Township, IL

The Fox River runs all the way through this small, 6-square-mile town. Of course, there’s all the hiking, biking, and camping in forest preserves near the river. But, if you really need a change of scenery, Santa’s Village Azoosment Park is a kitschy Christmas-themed attraction with carnival rides and a petting zoo (it’s open May through October).

3. Fox Lake

Fox Lake, IL

Part of the Chain O’ Lakes region, Fox Lake is a great waterfront getaway. Fishing enthusiasts and outdoorsy folks will love that the harbors and marinas with boat rentals all around the lake. If your up for trying something more active, Wilmot Mountain is just 15 minutes north. In the summer, it’s the site of obstacle courses and other athletic events. Come winter, the hills are filled with snow bunnies learning to ski.

4. Woodstock

Woodstock, IL 60098

Although its claim to fame lies in a little Bill Murray film called Groundhog Day, Woodstock’s idyllic small-town scenery has other charms such as the brick streets and old buildings. The town square is on the National Register of Historic Places and features a historic opera house built in 1889 with Carpenter Gothic and Moorish influences.

5. New Buffalo

New Buffalo, MI 49117

Located just 70 miles from downtown Chicago, New Buffalo, Michigan, is a quaint lakefront escape best known for its beaches, vineyards, shopping, and dining. Explore downtown on your own or sign up for a tour of the area’s many wine tasting rooms and distilleries. For nature-lovers, nearby Galien River County Park is a great waterfront hiking spot.

6. Lake Geneva

Lake Geneva, WI 53147

A favorite getaway among Chicagoans, Lake Geneva is a small town with stately mansions. The 26-mile Shore Path, previously used for thousands of years by Native American tribes, circles the entire lake, and it’s the perfect opportunity to see the area’s storied mansions up-close. Don’t miss Stone Manor, the largest historic home on the lake, and the Wrigley Estates, a collection of properties built by the chewing gum king.

7. Ottawa

Ottawa, IL 61350

Ottawa is only 15 minutes away from Illinois’ most popular natural area: Starved Rock State Park. Drawing in travelers with its waterfall and stunning hiking trails, Ottawa has its own eye-catching views, resting along both the Fox and Illinois rivers. The town center, Washington Square, is a historic district anchored by the Reddick Mansion. The Italianate home is one of the largest and most ornate residences built in the mid-1800s in the Midwest.

8. St. Joseph

St Joseph, MI

St. Joe’s tag line? The Riviera of the Midwest. See sand dunes along the lakeshore and later on, explore the countryside’s orchards and vineyards. The picture-perfect lighthouse at the end of a long pier is one of the most scenic places. But, it’s worth it to check out the downtown shopping district, the shoreline on Silver Beach, and the views from Lake Bluff Park.

9. Winamac

Winamac, IN 46996

This Indiana town is really all about its location along the Tippecanoe River. In fact, the name Winamac comes from the native Algonquian word for “Catfish.” Head to Tippecanoe River State Park for camping, kayak rentals, hiking trails, bike paths, and birding areas. Be sure to climb to the top of the Fire Tower for unparalleled tree-top vistas.

10. Fort Atkinson

Fort Atkinson, WI

Nestled along the Rock River, Fort Atkinson got its start in 1832 as, you guessed it, a military fort. Nowadays, there’s plenty of entertainment to go around with a vibrant community theater scene, music festivals, and the celebrated Fireside Theatre, marked by its can’t-miss-it, blaze-orange sculpture designed in 1970 by a local art teacher. Cyclists should check out the sculpture-lined Glacial River Bike Trail.

11. Cedarburg

Cedarburg, WI

Going to Cedarburg can feel a lot like stepping out of a time machine. The limestone buildings, preserved since the 1840s, now act as destinations for meandering tourists with shops, artists’ studios, restaurants, and an award-winning winery. The town’s covered bridge, built in 1876, is one of the last remaining examples in the entire state. The retired structure was made from local pine trees and milled 100 miles away in Baraboo.

12. Fulton

Fulton Township, IL 61252

In Fulton, take a self-guided tour through Heritage Canyon, a forested area that spotlights 19th-century structures like the Canyon Church, blacksmith shop, and schoolhouse. And with its Dutch heritage, it’s only natural that this town has a bucolic windmill, originally manufactured in the Netherlands.

13. Kohler

Kohler, WI

The village of Kohler is the epitome of Midwestern charm. The five-star resort The American Club, rooted in its beginnings in 1918 as a home to European immigrant workers, is no stranger to twinkling lights and horse-drawn carriage rides. Here, you can relax with therapeutic water treatments at the Kohler Waters Spa or take a factory tour to see how the company makes vitreous china sinks and 6-foot cast iron tubs.

14. New Glarus

New Glarus, WI 53574

The fingerprints of New Glarus’ Swiss settlers can still be witnessed today through the town’s buildings and murals—many of them look as if they’ve been plucked from the Alps. When you visit sample cheese curds and the local ale at New Glarus Brewing. The brewery sits on a hilltop and the outdoor patio is clad in limestone steps with a remnants of what very well could be a European castle.

15. Elkhart Lake

Elkhart Lake, WI

About an hour north of Milwaukee, there’s a lakeside locale that’s both peaceful—tall cedars, gentle waves lapping at the shore—as well as heart-pounding. Home to Road America racetrack, Elkhart Lake’s road-racing history began back in the 1950s on its public roads. Visitors can still cruise the original street circuit with historical markers along the way.

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16. Galena

Galena, IL 61036

The picturesque town is sure to recharge. More than three-quarters of Galena’s buildings are listed in the National Register of Historic Places. There’s an abundance of 1800’s architecture to admire as you amble along the town’s illustrious Main Street, coined “Helluva Half Mile” and brimming with delightful antique shops and restaurants. Don’t miss the Aldrich Guest House—a bed and breakfast set in an 1845 Greek Revival mansion.

17. Spring Green

Spring Green, WI 53588

Spring Green is your typical Wisconsin town, except for the local attractions. People are often surprised to learn that Frank Lloyd Wright’s home Taliesin resides in this quiet community. Down the road, you’ll find The House on the Rock, an architectural wonder built by Alex Jordan in 1945 to showcase his quirky collections. Also, be sure to take in a Shakespearean performance at the renowned American Players Theatre.

18. Quincy

Quincy, IL

Quincy is the furthest destination on our list but is worth the trip. The town is an architecture aficionado’s wonderland and features thousands of buildings in four National Historic Register Districts. Some are homes were constructed before the Civil War with distinct European influences, while others echo Frank Lloyd Wright’s Prairie style designs. Take a self-guided architecture driving tour or follow a guide to explore the area’s private homes.