Day Trips & Weekend Getaways from Chicago

By Rosalind Cummings-Yeates, author of Moon 52 Things to Do in Chicago

From scenic lakefronts and mouthwatering bites to refreshing hikes and literary history, there are plenty of options for a Midwest escape. Enjoy an afternoon away with these unique day trips from Chicago or head out of state for a weekend getaway—whatever you’re looking for, we’ve got you covered.

Day Trips

Explore the eclectic in Evanston

lighthouse in evanston illinois
Gross Point Lighthouse in Evanston. Photo © Jim Roberts/Dreamstime.

Why go: Find unexpected attractions in this quirky lakefront suburb.
Where: 13 miles north of downtown via Lake Shore Dr./U.S. 41 • L train Purple Line to
Timing: Spend a day wandering the town’s sights.

Set along the shores of Lake Michigan and dotted with Victorian homes and landscaped boulevards, Evanston is a picturesque village that draws lots of attention. Home of Northwestern University and noted for its diversity and liberal political activism, it’s the rare suburb with a hip reputation. Adding to its progressive renown, in 2021 Evanston became the first city in the United States to approve a reparations program for African Americans. The town’s progressive politics and openness to different perspectives has created an environment that has spawned quite a few quirky sights.

Retrace Hemingway’s footsteps in Oak Park

Why go: Head to this leafy suburban village to gain insight into one of its famous sons.
Where: 10 miles west of the Loop via I-290 • L train Green Line to Oak Park
Timing: Although only a 20-minute drive from downtown, Oak Park feels worlds away and deserves a full afternoon to explore.

With Victorian houses painted in crayon colors and rolling, emerald lawns flanked by blooming trees, Oak Park is a picturesque small town. It’s also famously the home of the world’s largest collection of Frank Lloyd Wright-designed buildings. But, for me, the most defining Oak Park creative is Ernest Hemingway, one of my favorite writers.

Walk in the woods at Morton Arboretum

Why go: Wander through miles of majestic landscape that make you feel like you’re in another country.
Where: 25 miles west of downtown Chicago via I-290/I-88 • 4100 Rte. 53 • Lisle, IL • 630/968-0074 • • $15 adults, $10 children
Timing: The drive to the arboretum from downtown Chicago takes 45-60 minutes, so once you’re here, settle in for the day. While a trip to the arboretum is worthwhile any time of year, it’s particularly spectacular in late October, during fall foliage.

Chicago is home to numerous parks and nature preserves, but if you want to feel like you’ve traveled to another part of the world, head to the Morton Arboretum. For a day out, I pack a hat, scarf, snacks, and a book, just like when I board a plane. On the drive up, the arboretum at first glance looks like just another strip of land amid the suburban sprawl. But once you park in the lot, you’ll start to catch glimpses of the gardens. Established in 1922, the Morton Arboretum is recognized as one of North America’s most comprehensive collections of trees and shrubs, encompassing 17,000 acres, with areas devoted to oaks, beeches, and maples; honeysuckles, roses, and magnolias; and the flora of Appalachia, Europe, Korea, and China.

Hike in Starved Rock State Park

wooden walkway through trees in Starved Rock state park
Starved Rock State Park. Photo © Eddie Rodriquez/Dreasmtime.
Why go: Wander trails through one of the state’s most beautiful landscapes.
Where: 100 miles southwest of Chicago via I-55 and I-80 • 2678 E. 875th Rd., Oglesby, IL • 815/667-4726 • free
Timing: The park is a great natural escape from the city for a day or weekend. It takes about 1.5 hours to drive there from downtown.

Starved Rock State Park became Illinois’ first state park in 1911. It covers 2,630 acres and contains several different ecosystems: oak, maple, cedar, and pine forests; prairies; and wetlands. It’s renowned for its 18 jaw-dropping sandstone canyons, formed by glacial meltwater and erosion over time. Every season at the park supplies a special treat. In spring and summer, the canyons glisten with waterfalls; in fall, the oak and maple forests turn deep crimson and gold; and in winter there are fewer hikers on the trails, the waterfalls transform into icefalls, and you might spot bald eagles soaring over the river—Plum Island, a 45-acre sanctuary in the middle of the Illinois River right across from the park, is a wintering spot for the birds.

Weekend Getaways from Chicago

Go back in time in Galena, Illinois

Why go: This remarkably preserved riverfront town transports you to the 19th century.
Where 165 miles northwest of Chicago via I-94 and U.S. 20
Timing: It takes about three hours to drive from Chicago to Galena. Expect to spend a relaxing weekend.

Illinois is filled with small towns, but few are as charming as Galena, located in the state’s northwestern corner. Surrounded by rolling hills and green valleys, and with red-brick Victorian buildings set along the Galena River—a tributary of the Mississippi River—this port town is a visual delight. Most of its streets and structures look as they did during the town’s 1860s heyday. Galena boasts more than 1,000 buildings listed on the National Register of Historic Places and is justifiably hailed as “an outdoor museum of the Victorian Midwest.”

Hit the beach in St. Joseph, Michigan

Why go: Bask by the lake in the charming “Riviera of the Midwest.”
Where: 100 miles east of Chicago via I-90 and I-94
Timing: It takes about 1.5-2 hours to drive to St. Joseph from Chicago. A weekend is the perfect amount of time to enjoy its offerings. Summer and early fall are the best seasons for a visit; many venues close by late fall.

St. Joseph’s is called the “Riviera of the Midwest.” Perched on a bluff along Lake Michigan’s shoreline and dotted with dune-filled beaches, it’s my favorite Midwestern beach town. It may be based around the same lake as Chicago, but the waters here seem to sparkle in a way I’ve never seen in the big city. The surrounding countryside, dotted with orchards and vineyards, also lends charm. Like most beach towns, St. Joe’s keeps a relaxed pace; this isn’t the place to be in a hurry or focusing on checking off a to-do list. Attractions can get crowded quickly, and service is slow-paced, but the warmth and friendliness of the locals make up for that.

Indulge in brats and brews in Milwaukee, Wisconsin

dusk over the milwaukee river
Milwaukee River. Photo © Alena Mozhjer/Dreamstime.
Why go: Delight in the delicious perks of this Midwestern city’s German heritage.
Where: 90 miles north of Chicago via I-94 • Amtrak’s Hiawatha line to Intermodal Station in downtown Milwaukee
Timing: It takes about 1.5 hours to drive to Milwaukee from Chicago. Make a summer weekend of it.

Milwaukee has its own sensibilities, a bit slower paced and grittier than Chicago, with a quirky German personality and burgeoning arts-friendliness and sophistication. Like Chicago, the city sits along Lake Michigan and was originally inhabited by Algonquin, Potawatomi, and Ojibwe people. French fur traders and missionaries established the area as a trading post in the late 18th century. Polish, Irish, and German immigrants poured into the city during the mid-19th century, the latter bringing their brewing and sausage-making traditions with them, heavily influencing the city’s developing culture.

Relax at Elkhart Lake, Wisconsin

Why go: Unwind in this charming 19th century-era resort town with modern amenities and amusements.
Where: 150 miles north of Chicago via I-94
Timing: It takes about 2.5 hours to drive to Elkhart Lake, which is a great place for a weekend getaway in the summer. Many venues close outside the prime season (Memorial Day-Labor Day). Book at least a month in advance for hotels.

Sometimes there’s nothing like leaving the fast pace of the big city and immersing yourself in the quiet of a small town. Elkhart Lake fits the bill. The pretty lakeside village has less than 1,000 residents and offers a singular vacation experience. Edging the shores of a pristine, sapphire blue lake—named by its original inhabitants, the Potawatomi, for its resemblance to an elk’s heart—and enveloped by the canopy of the lush Kettle Moraine forest, the town is a dreamy retreat.

Dine lakeside in Madison, Wisconsin

Why go: There’s no better way to enjoy this vibrant city that’s sandwiched between two lakes than by partaking in its waterfront food scene.
Where: 150 miles northwest of Chicago via I-90
Timing: It takes about 2.5 hours to drive to Madison. Spend a weekend in the summer.

Madison is mostly noted for being a college town—home as it is to the flagship University of Wisconsin campus—as well as the state capital, but it’s also one of only two cities in the country built on an isthmus. Downtown is nestled between Lake Mendota to the west and Lake Monona to the east, lending this mid-sized Midwestern town a breezy urban oasis vibe. Madison is also an unexpected foodie destination with a thriving restaurant scene. The best way to enjoy this atypical town is to combine these two features.

Enjoy the bounty of Door County, Wisconsin

Why go: From beaches and forests to orchards, vineyards, and culinary treats, this striking peninsula has it all.
Where: 235 miles north of Chicago via I-94 and I-43
Timing: It takes almost four hours to drive from Chicago to Sturgeon Bay, the closest and largest city in Door Country. Plan on a long weekend, at least.

If you’ve never traveled to Door County, Wisconsin, you’ve been missing out on the ultimate Midwest getaway. This stunning, pine-covered peninsula is your best bet for a nearby, year-round excursion. It’s been called the “Cape Cod of the Midwest,” with its 300 miles of shoreline and historic lighthouses. A narrow strip of land between Green Bay and Lake Michigan—only about 18 miles wide and 70 miles long—it’s truly a natural paradise, featuring an unusual landscape of wetlands, forests, sand dunes, limestone slopes, sea caves, and outlying islands. Adding to the magic, Door County encompasses a number of delightful small towns offering their own charms. Sturgeon Bay is the peninsula’s gateway town. But my favorites to base myself in are Fish Creek, Ephraim, and Sister Bay—all located in close proximity farther north along the peninsula’s western side—which offer great restaurants, inns, and access to parks. Highways 42 and 57 are the primary routes around the peninsula, and it takes about an hour to drive from one end to the other.

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