By Rosalind Cummings-Yeates, writer of Moon 52 Things to Do in Chicago
From scenic lakefronts and mouthwatering bites to refreshing hikes and literary historical past, there are many choices for a Midwest escape. Take pleasure in a day away with these distinctive day journeys from Chicago or head out of state for a weekend getaway—no matter you’re searching for, we’ve bought you lined.
Day Journeys
Discover the eclectic in Evanston

Why go: Discover sudden sights on this quirky lakefront suburb.
The place: 13 miles north of downtown by way of Lake Shore Dr./U.S. 41 • L practice Purple Line to
Davis
Timing: Spend a day wandering the city’s sights.
Set alongside the shores of Lake Michigan and dotted with Victorian houses and landscaped boulevards, Evanston is a picturesque village that attracts a lot of consideration. House of Northwestern College and famous for its variety and liberal political activism, it’s the uncommon suburb with a hip fame. Including to its progressive renown, in 2021 Evanston turned the primary metropolis in the USA to approve a reparations program for African People. The city’s progressive politics and openness to totally different views has created an atmosphere that has spawned fairly a number of quirky sights.
Retrace Hemingway’s footsteps in Oak Park
Why go: Head to this leafy suburban village to achieve perception into one among its well-known sons.
The place: 10 miles west of the Loop by way of I-290 • L practice Inexperienced Line to Oak Park
Timing: Though solely a 20-minute drive from downtown, Oak Park feels worlds away and deserves a full afternoon to discover.
With Victorian homes painted in crayon colours and rolling, emerald lawns flanked by blooming bushes, Oak Park is a picturesque small city. It’s additionally famously the house of the world’s largest assortment of Frank Lloyd Wright-designed buildings. However, for me, probably the most defining Oak Park artistic is Ernest Hemingway, one among my favourite writers.
Stroll within the woods at Morton Arboretum
Why go: Wander by way of miles of majestic panorama that make you are feeling such as you’re in a foreign country.
The place: 25 miles west of downtown Chicago by way of I-290/I-88 • 4100 Rte. 53 • Lisle, IL • 630/968-0074 • www.mortonarb.org • $15 adults, $10 kids
Timing: The drive to the arboretum from downtown Chicago takes 45-60 minutes, so when you’re right here, settle in for the day. Whereas a visit to the arboretum is worth it any time of yr, it’s significantly spectacular in late October, throughout fall foliage.
Chicago is dwelling to quite a few parks and nature preserves, however if you wish to really feel such as you’ve traveled to a different a part of the world, head to the Morton Arboretum. For a day trip, I pack a hat, scarf, snacks, and a guide, similar to after I board a airplane. On the drive up, the arboretum at first look appears like simply one other strip of land amid the suburban sprawl. However when you park within the lot, you’ll begin to catch glimpses of the gardens. Established in 1922, the Morton Arboretum is acknowledged as one among North America’s most complete collections of bushes and shrubs, encompassing 17,000 acres, with areas dedicated to oaks, beeches, and maples; honeysuckles, roses, and magnolias; and the flora of Appalachia, Europe, Korea, and China.
Hike in Starved Rock State Park

Why go: Wander trails by way of one of many state’s most lovely landscapes.
The place: 100 miles southwest of Chicago by way of I-55 and I-80 • 2678 E. 875th Rd., Oglesby, IL • 815/667-4726 • free
Timing: The park is a good pure escape from town for a day or weekend. It takes about 1.5 hours to drive there from downtown.
Starved Rock State Park turned Illinois’ first state park in 1911. It covers 2,630 acres and comprises a number of totally different ecosystems: oak, maple, cedar, and pine forests; prairies; and wetlands. It’s famend for its 18 jaw-dropping sandstone canyons, shaped by glacial meltwater and erosion over time. Each season on the park provides a particular deal with. In spring and summer season, the canyons glisten with waterfalls; in fall, the oak and maple forests flip deep crimson and gold; and in winter there are fewer hikers on the paths, the waterfalls rework into icefalls, and also you would possibly spot bald eagles hovering over the river—Plum Island, a 45-acre sanctuary in the course of the Illinois River proper throughout from the park, is a wintering spot for the birds.
Weekend Getaways from Chicago
Return in time in Galena, Illinois
Why go: This remarkably preserved riverfront city transports you to the Nineteenth century.
The place 165 miles northwest of Chicago by way of I-94 and U.S. 20
Timing: It takes about three hours to drive from Chicago to Galena. Count on to spend a soothing weekend.
Illinois is full of small cities, however few are as charming as Galena, situated within the state’s northwestern nook. Surrounded by rolling hills and inexperienced valleys, and with red-brick Victorian buildings set alongside the Galena River—a tributary of the Mississippi River—this port city is a visible delight. Most of its streets and constructions look as they did throughout the city’s 1860s heyday. Galena boasts greater than 1,000 buildings listed on the Nationwide Register of Historic Locations and is justifiably hailed as “an out of doors museum of the Victorian Midwest.”
Hit the seashore in St. Joseph, Michigan
Why go: Bask by the lake within the charming “Riviera of the Midwest.”
The place: 100 miles east of Chicago by way of I-90 and I-94
Timing: It takes about 1.5-2 hours to drive to St. Joseph from Chicago. A weekend is the right period of time to get pleasure from its choices. Summer time and early fall are the perfect seasons for a go to; many venues shut by late fall.
St. Joseph’s known as the “Riviera of the Midwest.” Perched on a bluff alongside Lake Michigan’s shoreline and dotted with dune-filled seashores, it’s my favourite Midwestern seashore city. It could be primarily based across the identical lake as Chicago, however the waters right here appear to glitter in a method I’ve by no means seen within the large metropolis. The encircling countryside, dotted with orchards and vineyards, additionally lends allure. Like most seashore cities, St. Joe’s retains a relaxed tempo; this isn’t the place to be in a rush or specializing in checking off a to-do record. Points of interest can get crowded rapidly, and repair is slow-paced, however the heat and friendliness of the locals make up for that.
Take pleasure in brats and brews in Milwaukee, Wisconsin

Why go: Delight within the scrumptious perks of this Midwestern metropolis’s German heritage.
The place: 90 miles north of Chicago by way of 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 season weekend of it.
Milwaukee has its personal sensibilities, a bit slower paced and grittier than Chicago, with a unusual German character and burgeoning arts-friendliness and class. Like Chicago, town sits alongside Lake Michigan and was initially inhabited by Algonquin, Potawatomi, and Ojibwe individuals. French fur merchants and missionaries established the realm as a buying and selling submit within the late 18th century. Polish, Irish, and German immigrants poured into town throughout the mid-Nineteenth century, the latter bringing their brewing and sausage-making traditions with them, closely influencing town’s growing tradition.
Loosen up at Elkhart Lake, Wisconsin
Why go: Unwind on this charming Nineteenth century-era resort city with trendy facilities and amusements.
The place: 150 miles north of Chicago by way of I-94
Timing: It takes about 2.5 hours to drive to Elkhart Lake, which is a good place for a weekend getaway in the summertime. Many venues shut outdoors the prime season (Memorial Day-Labor Day). E-book a minimum of a month prematurely for resorts.
Generally there’s nothing like leaving the quick tempo of the large metropolis and immersing your self within the quiet of a small city. Elkhart Lake suits the invoice. The beautiful lakeside village has lower than 1,000 residents and presents a singular trip expertise. Edging the shores of a pristine, sapphire blue lake—named by its authentic inhabitants, the Potawatomi, for its resemblance to an elk’s coronary heart—and enveloped by the cover of the plush Kettle Moraine forest, the city is a dreamy retreat.
Dine lakeside in Madison, Wisconsin
Why go: There’s no higher option to get pleasure from this vibrant metropolis that’s sandwiched between two lakes than by partaking in its waterfront meals scene.
The place: 150 miles northwest of Chicago by way of I-90
Timing: It takes about 2.5 hours to drive to Madison. Spend a weekend in the summertime.
Madison is usually famous for being a school city—dwelling as it’s to the flagship College of Wisconsin campus—in addition to the state capital, nevertheless it’s additionally one among solely two cities within the nation constructed on an isthmus. Downtown is nestled between Lake Mendota to the west and Lake Monona to the east, lending this mid-sized Midwestern city a breezy city oasis vibe. Madison can also be an sudden foodie vacation spot with a thriving restaurant scene. One of the best ways to get pleasure from this atypical city is to mix these two options.
Benefit from the bounty of Door County, Wisconsin
Why go: From seashores and forests to orchards, vineyards, and culinary treats, this putting peninsula has all of it.
The place: 235 miles north of Chicago by way of I-94 and I-43
Timing: It takes nearly 4 hours to drive from Chicago to Sturgeon Bay, the closest and largest metropolis in Door Nation. Plan on a protracted weekend, a minimum of.
For those who’ve by no means traveled to Door County, Wisconsin, you’ve been lacking out on the final word Midwest getaway. This gorgeous, pine-covered peninsula is your finest guess for a close-by, year-round tour. It’s been referred to as the “Cape Cod of the Midwest,” with its 300 miles of shoreline and historic lighthouses. A slim strip of land between Inexperienced Bay and Lake Michigan—solely about 18 miles broad and 70 miles lengthy—it’s really a pure paradise, that includes an uncommon panorama of wetlands, forests, sand dunes, limestone slopes, sea caves, and outlying islands. Including to the magic, Door County encompasses plenty of pleasant small cities providing their very own charms. Sturgeon Bay is the peninsula’s gateway city. However my favorites to base myself in are Fish Creek, Ephraim, and Sister Bay—all situated in shut proximity farther north alongside the peninsula’s western aspect—which supply nice eating places, inns, and entry to parks. Highways 42 and 57 are the first routes across the peninsula, and it takes about an hour to drive from one finish to the opposite.