BEST Weekend Getaways From Chicago in 2023 (From a Local)

The best weekend getaways from Chicago in 2023 whether you love nature, beaches, cities or small towns. From romantic getaways for couples to fun vacations for friends or families, there is something for everyone on this list.

Best Weekend Getaways From Chicago

Looking for the best weekend trip from Chicago? Fortunately there are many places in the United States (and even Canada) that are a short drive or flight away. You will love these weekend getaways from Chicago – from amazing places in the Midwest that you can easily drive to from Chicago to a few incredible cities that are only a short flight away.

(And make sure to check out my essential road trip packing list (with free printable pdf) if you are driving or my carry on packing list to make sure you have all your travel essentials before you go!)

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Lake Geneva, Wisconsin

Lake Geneva Wisconsin is one of the best weekend getaways from Chicago

Lake Geneva, a resort city on the shore of Geneva Lake is a popular vacation destination from Chicago. In fact, wealthy Chicagoans built their mansions here during the Gilded Age. Visitors can still get an up close view of these beautiful homes by walking the 20 mile Geneva Lake Shore Path around the lake.

If being in the water is more your thing, you can rent just about anything (speedboats, jetskis, kayaks, pontoons, etc) for an adventurous day. While Lake Geneva is a great place for some beach fun, visitors can also enjoy zip-lining, a waterpark, golf, a petting zoo, spas and more.

Lake Geneva is also a great destination for a winter weekend getaway as visitors can go skiing and snowboarding or visit the ice castles.

Read about the best things to do in Lake Geneva here.

Stay: Grand Geneva Resort & Spa

Getting There: By Car: Lake Geneva is only 83 miles from Chicago

Elkhart Lake, Wisconsin

Elkhart Lake is a less known weekend getaway from Chicago

Elkhart Lake is a quaint town where visitors can really experience an authentic summer lake getaway but also enjoy the year-round offerings. Take a dip in the crystal clear waters, experience the various watersports (paddleboarding, kayaking, jet skiing), go fishing or just lounge around on a pool float.

While the lake is a big draw, there is so much more to the area. From hiking the picturesque Kettles, The Ice Age Trail or along the shore of Lake Michigan, there is no shortage of beautiful hiking spots. Golf enthusiasts will appreciate the top golf destinations located less than 30 minutes away. Motorsports lovers and thrill seekers will want to check out Road America Racetrack, North America’s longest natural road racing facility.

The fun doesn’t end when summer is over. Dog sledding, snowshoeing, skiing and carriage rides are available for winter time fun.

Stay: The Osthoff Resort

Getting There: By Car: Elkhart Lake is 150 miles from Chicago (about 2.5 hour drive)

Galena, Illinois

Galena Illinois is one of the best weekend getaways from Chicago

Galena is short road trip from Chicago but it is a great place for a weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House.

Some things to do in Galena including shopping downtown at the many boutiques and antique stores, eating at local restaurants and wine tasting at local vineyards or exploring the lush rivers and hiking trails dotted throughout the area. Galena is close to Apple River Canyon State Park, an Illinois state park, where you can go hiking, fishing and more.

Stay: Country Inn & Suites by Radisson

Getting There: By Car: 164 miles driving distance from Chicago

Cheap Car Rentals

Dubuque, Iowa

Dubuque, Iowa’s oldest town, is located across the Mississippi River about 20 minutes from Galena, Illinois. With its historic architecture and hilly landscape, Dubuque is worth visiting year round.

Some of the best things to do in Dubuque including visiting the 14-acre National Mississippi River Museum & Aquarium and enjoyng spectacular views of the river from Eagle Point Park.

From April though November, visitors can ride Fenelon Place Elevator Company (also known as the Fourth Street Elevator), a historic cable car. This funicular railway has been called “the world’s steepest, shortest scenic railway” and has great views of downtown Dubuque, the Mississippi River and 3 states.

Winter activities include skiing and snowboarding at Sundown Mountain Resort, cross country skiing, snowshoeing and hiking.

Stay: Hotel Julien Dubuque

Getting There: By Car: Dubuque is 178 miles from Chicago (just over a 3 hour drive)

Milwaukee, Wisconsin

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Stay: Brewhouse Inn and Suites (boutique hotel housed in what was once the main Pabst brewery building)

Getting There:
By Car:  93 miles driving distance
By Train: Amtrak Hiawatha train offers frequent daily service between Milwaukee and Chicago.
By Air: It probably does not make sense to fly but there are daily nonstop flights from Chicago O’Hare to Milwaukee Mitchell International Airport (MKE)

New Buffalo, Michigan

New Buffalo, Michigan is a charming beach town on the shores of Lake Michigan. The beaches face west and have beautiful sunsets.

In addition to the beaches, a must see attraction is Galien River County Park, a beautiful park with boardwalk paths through the marsh.  For those that enjoy gambling, New Buffalo is home to the Four Winds Casino Resort.

Getting There:
By Car: 70 miles driving distance
By Train: New Buffalo has daily Amtrak service from Chicago on the Blue Water and Wolverine lines.

South Bend, Indiana

One of the best things to see in South Bend is the Studebaker National Museum, featuring a large collection of Studebaker automobiles drawn from the history of the company, beginning with horse-drawn carriages. They also have the carriage that Abraham Lincoln took to Ford’s Theater the night he was assassinated.

For those with a sweet tooth, visit the South Bend Chocolate Company, which is home to one of the largest collections of chocolate memorabilia in the world, including a 1,300-year-old Mayan chocolate pot among the hundreds of tins, containers and chocolate boxes of all shapes and sizes.  Visitors can take a factory tour for a history lesson of chocolate and its origins, as a guide leads guests through all of the factory processes, including panning, enrobing and more, including a test sample at the end. For an extra special treat, you’ll dip a chocolate spoon, walk through the Chocolate Museum and receive 10% off your purchase that day.

South Bend is famous for being home to the University of Notre Dame. There are many attractions on the beautiful, large campus including the Golden Dome, Notre Dame Stadium, the Basilica of the Sacred Heart and the Grotto of Our Lady of Lourdes, a replica of the famous shrine.

Stay: Aloft South Bend or Morris Inn at Notre Dame (if you want to stay on-campus)

Getting There:
By Car:  96 miles driving distance
By Train: South Shore Line commuter rail runs multiple daily trains between Millennium Station in downtown Chicago and South Bend Airport station.
By Air: United Express has multiple daily flights from Chicago O’Hare and South Bend International Airport (SBN)

Madison, Wisconsin

In addition to being the capital of Wisconsin, Madison is a fun college town full of cafes, breweries, restaurants, bookstores and other attractions. For those that enjoy being outdoors, Madison is a good base for nature-filled activities in the area including hiking, biking, fishing and boating.

Getting There: By Car: 147 miles driving distance from Chicago

Holland, Michigan

Located on the shores of Lake Michigan, the city of Holland, Michigan, which was founded by Dutch Calvinists in the late 1840s, proudly flaunts its Dutch origins, and is home to canals and a 250-year-old authentic Dutch windmill.

Holland is especially pretty in the spring when you can see colorful tulips in local gardens, parks, attractions and lining the streets. You can see millions of tulips at Veldheer Tulip Gardens. One of the mont popular times to visit is during the Tulip Time Festival, the largest tulip festival in the United States which is held every year in May.

Stay: Courtyard by Marriott Holland Downtown

Getting There: By Car: 150 miles driving distance from Chicago

Door County, Wisconsin

Door County, located in the northeast corner of Wisconsin, is a hidden gem full of charming villages and towns, lighthouses, state parks, vineyards, and outdoor attractions and activities.

Sturgeon Bay is a convenient base for exploring the area. The city is a fisherman’s mecca, with some of the best bass fishing in the world. You can also tour a restored tug, visit the Door County Maritime Museum, learn the history of Door County, stroll down historic 3rd Avenue, or enjoy nature at Potawatomi State Park on the city’s edge.

Explore one or more of several little towns located along the east and northeast coastline of Door County which full of unique shops, galleries, restaurants and breweries.

Bring your car or bike on the 30 minute ferry to Washington island, located northeast of the tip of the Door Peninsula.

Stay: Sturgeon Bay, Egg Harbor, Fish Creek, Bailey’s Harbor or Sister Bay all have good options

Getting There: By Car: 244 miles driving distance to Sturgeon Bay

Shawnee National Forest

Nestled between the Mississippi and Ohio Rivers in southern Illinois, the Shawnee National Forest is full of natural beauty, making it ideal for outdoor recreation from hiking to climbing.

The stunning Shawnee National Forest landscape features woodlands, hills, lakes, creeks, rock formations, cliffs and bluffs. You can also see wildlife such as bad eagles.

Shawnee National Forest is the best place to go hiking in Illinois with spectacular views. Trails include the long River to River Trail and the Rim Rock National Recreational Trail. The must see attraction is the Garden of the Gods wilderness area featuring ancient sandstone cliffs and formations.  Climbers should not miss the Jackson Falls climb on 60 feet of sandstone cliffs and boulders that include numerous freestanding towers.

If you enjoy wine, The Shawnee Hills Wine Trail features 11 wineries located along a 35-mile scenic drive along highway 127 and highway 51 in the Shawnee National Forest.

Stay: Riverview Mansion Hotel (a unique boutique style mansion)

Getting There: By Car: 300 miles driving distance from Chicago

Do you prefer to fly rather than drive? Here are a few cities worth visiting for the weekend that are only a short flight away.

Toronto, Canada

Canadian bucket list places to visit in canada during the summer

Although Toronto is in a different country, it is only a short flight away. You can even drive there in one day but that is long drive unless you have a long weekend.

Toronto is very similar to Chicago in that it offers great theater, shopping and restaurants. The CN Tower, the tallest freestanding structure in the Western Hemisphere is a must see attraction. If you are feeling brave, try the EdgeWalk, a walk outside on the ledge encircling the top of the CN Tower. Other must see places are St. Lawrence Market and the Distillery District.

Looking for more things to do in Toronto? Here is a 3 days in Toronto itinerary written by a local.

Stay: Fairmont Royal York (located right by Union Station)

Getting There:
By Air: Several airlines offer nonstop flights between Chicago O’Hare and Toronto Pearson International Airport (YYZ) which is approximately a 1.5-2 hour flight.
By Car:  523 miles (about 8.5 hour drive)

Atlanta, Georgia

Atlanta, Georgia is another great city for a weekend getaway especially if you want to indulge in some southern food.  Some must see attractions (especially for families) include Piedmont Park, Georgia Aquarium, College Football Hall of Fame and the World of Coke. Here are the best things to do with 2 days in Atlanta.

Getting There:

By Air: There are numerous flight options between Chicago and Atlanta from both Chicago O’Hare and Chicago Midway. Flight time is approximately 2 hours.

New York City

New York City is an easy city to fly to for the weekend. Here are the best things to do with 2 days in NYC.

Getting There:

By Air: There are numerous flight options between Chicago and New York City from both Chicago O’Hare and Chicago Midway. Flight time is approximately 2 -2.5 hours.

What are your favorite weekend getaway from Chicago?


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