Weekend Trips From Chicago: 10 Places To Go To Escape The Big City

Need an escape from the noise of the big city? Fortunately, Chicago is surrounded by incredible cities and small towns that make for perfect weekend getaways. Whether you're craving a taste of nature, cultural exploration, or simply some relaxation, there's a retreat waiting just beyond the city limits. Let's dive into 10 unforgettable weekend trips from Chicago, each offering its own unique charm and allure.

Table of Contents:

1. Exploring Milwaukee's Breweries

2. Explore Nature in Door County

3. Adventures in Starved Rock State Park

4. Cultural Delights in Madison

5. Scenic Beauty of Lake Geneva

6. Historic Charm of Galena

7. Thrills and Entertainment in Indianapolis

8. Nature's Wonders at Michigan's Sleeping Bear Dunes

9. Tranquil Escape to Michigan City

10. Charming Getaway in St. Louis

1 —

Exploring Milwaukee’s Breweries

Travel Time:

• Car - 1hr 45mins

• Train - 1hr 30 mins via Amtrak’s Hiawatha Service

• Bus - 2hr 15mins

Milwaukee, a beer lover's paradise, is just 1.5 hours away from Chicago, making it a perfect choice for weekend trips from Chicago. Whether you drive or take the train, the journey is straightforward. Opting for the train means you'll be conveniently dropped off in the city without worrying about parking. Departing from Union Station, you can explore Milwaukee's vibrant brewing scene hassle-free. Sample iconic brews from Miller and Pabst, and discover craft breweries for a memorable "weekend trips from Chicago" adventure.

2 —

Explore Nature in Door County

Travel Time:

• Car - 4hr 30mins

• Train - None

• Bus - None

Door County, Wisconsin, is just a scenic 3-hour drive or train ride from Chicago, making it a perfect choice for weekend trips from Chicago. This tranquil peninsula offers picturesque landscapes and serene beaches for a perfect getaway. Indulge in delicious cherry pie, explore charming art galleries, and bask in the peaceful ambiance. Whether you're driving or taking the train, Door County is the ideal destination to unwind and recharge away from the city bustle.

3 —

Unwind in Starved Rock State Park

Travel Time:

• Car - 1hr 30mins

• Train - None

• Bus - None

Towering canyons, cascading waterfalls, and lush forests at Starved Rock offer a tranquil escape, making it a perfect choice for weekend trips from Chicago. Whether hiking scenic trails, kayaking along the Illinois River, or simply soaking in the natural beauty, Starved Rock promises rejuvenating adventures just a short journey away from the city.

4 —

Discover Delights in Madison

Travel Time:

• Car - 3hr 30mins

• Train/Bus - 3hr 5 mins via Amtrak’s Hiawatha Service to Milwaukee & Thruway Connecting Coach to Madison

• Bus - 3hr 45min

Discover the vibrant capital city of Madison, Wisconsin, offering a blend of culture, cuisine, and natural beauty, making it a great destination for weekend trips from Chicago. Explore the State Capitol, stroll by Lake Mendota, and indulge in farm-to-table dining experiences.

5 —

Scenic Beauty of Lake Geneva

Photo: Visit Lake Geneva

Travel Time:

• Car - 1hr 45mins

• Train/Bus- 5hr 30 mins

• Bus Only - 6hr 15mins

Nestled in Wisconsin's countryside, Lake Geneva beckons with its serene beauty, making it an ideal choice for weekend trips from Chicago. Relax on sandy beaches, cruise on crystal-clear waters, and explore charming lakeside towns and boutiques. This picturesque destination offers a range of activities, from leisurely boat tours to adventurous hikes in nearby trails. Whether you're looking for a peaceful retreat or an active getaway, Lake Geneva provides the perfect blend of relaxation and excitement for a memorable escape from the city.

6 —

Historic Charm of Galena

Travel Time:

• Car - 3hr

• Train - None

• Bus - 4hr 15min

Step back in time in Galena, Illinois, renowned for its preserved 19th-century architecture and charming Main Street. Enjoy boutique shopping, historic home tours, and outdoor adventures in the surrounding area. This historic town offers a unique blend of history, culture, and natural beauty, making it a delightful destination. Galena is a perfect spot for weekend trips from Chicago, where you can unwind and immerse yourself in a slower-paced, enriching environment.

7 —

Thrills and Entertainment in Indianapolis

Travel Time:

• Car - 3hr

• Train - 5hr

• Bus - 3hr 20mins

Embark on an adventure to Indianapolis, just a few hours' drive from Chicago. Explore iconic attractions like the Motor Speedway, delve into museums, and savor diverse culinary delights. This vibrant city offers a mix of sports history, artistic culture, and gastronomic experiences, making it an enriching destination. Indianapolis is an ideal choice for weekend trips from Chicago, where you can discover new facets of Midwestern charm and innovation.

8 —

Nature's Wonders at Michigan's Sleeping Bear Dunes

Photo: Sleeping Bear Dunes Visitors Bureau

Travel Time:

• Car - 5hr

• Train - None

• Bus - None

Experience the breathtaking beauty of Sleeping Bear Dunes National Lakeshore, offering towering sand dunes, pristine beaches, and scenic trails. Witness unforgettable sunsets and stargazing opportunities. This natural paradise provides a tranquil escape with its stunning landscapes and serene atmosphere. Sleeping Bear Dunes is an excellent choice for weekend trips from Chicago, where you can connect with nature and enjoy a variety of outdoor activities in a majestic setting.

9 —

Tranquil Escape to Michigan City

Travel Time:

• Car - 1hr

• Train - 2hr

• Bus - None

Find tranquility in Michigan City, Indiana, with its pristine beaches, scenic parks, and vibrant downtown scene. Explore art centers, historic sites, and waterfront dining options for a relaxing weekend escape. This charming city combines natural beauty with cultural richness, offering a diverse array of activities for every visitor. Michigan City is a fantastic destination for weekend trips from Chicago, where you can unwind and experience the best of lakeside leisure and urban exploration.

9 —

Charming Getaway in St. Louis

Travel Time:

• Car - 4hr 30mins

• Train - 5hr

• Bus - 9.5hr 15mins

Discover the charm of St. Louis, Missouri, boasting iconic landmarks, museums, and entertainment districts. From the Gateway Arch to cultural experiences, there's something for everyone in this vibrant city. Enjoy exploring diverse neighborhoods, sampling delicious cuisine, and experiencing live music and performances. St. Louis is an excellent destination for weekend trips from Chicago, offering a blend of history, culture, and modern attractions for a memorable getaway.

As we wrap up our journey through these 10 weekend trips from Chicago, it's amazing to see the variety of experiences just a short drive or train ride away. From Milwaukee's vibrant breweries to the historic allure of Galena, each destination offers its own unique charm. Whether you're in search of the tranquil beaches of Door County or the rich cultural tapestry of Madison and St. Louis, there's a perfect escape for every Chicagoan. So pack your bags and set off on a weekend adventure that will rejuvenate and inspire you, leaving you with cherished memories until your next escape from the city.