I've always had a fun time visiting Chicago, especially on a family vacation. Once we started exploring other parts of Illinois, I realized how much we had been missing. I enjoyed exploring courthouse squares, bookstores in old train depots in small towns all around Illinois. Traveling through the state with my husband and son, I kept saying, “I didn’t expect to love this part so much.” And then I’d say it again an hour later.
Best Places to Visit in Illinois:
Springfield, Illinois: Lincoln’s Legacy and Small-Town Pride
Springfield didn’t exactly have the vibe of a capital city. As we pulled into town, I said to my husband, “I'm glad we finally made this trip.”
We began at the Abraham Lincoln Presidential Library and Museum. My son was amazed at the recreated log cabin and the candlelit White House.
Outside, downtown Springfield had wide streets, tidy storefronts, and a few bronze statues.
What I Loved Most: Springfield blended reverence and warmth. I liked that the city was both historic and modern.
My highlights? Lunch at Café Moxo. I ordered their pot roast sandwich with mashed potatoes and gravy, served on toasted ciabatta.
There are many great hotels for an overnight stay (from $98). We tried Crowne Plaza Springfield by IHG ($113) and the views were great!
Plan your Springfield trip:
- Drive Time from Chicago: ~3.5 hours southwest
- Vibe: Historic, proud, quietly moving
- Best For: History lovers, thoughtful weekenders, road trippers
- Lodging: The Inn at 835, State House Inn, local guesthouses
- Dining: Café Moxo, Obed & Isaac’s, Maldaner’s
- Activities: Abraham Lincoln sites, Dana-Thomas House, Route 66 Drive-In, Washington Park
- Best Time to Visit: Fall for golden leaves and fewer crowds
Chicago, Illinois: Markets, Murals, and Morning Heat
Chicago always wakes up before I do. By the time we stepped off the train at Ogilvie, the streets were already buzzing, the skyline cutting into a sky streaked with light. I turned to my husband and said, “Let’s find something warm, flaky, and made with butter.” We didn’t have to go far.
The Chicago French Market sat just around the corner—part commuter hub, part treasure trove. Inside, it smelled like fresh bread, espresso, spice, and sugar. We drifted past counters stacked with éclairs and croissants, then stopped at Vanille Patisserie. I ordered a ham and cheese croissant, still warm from the oven. The layers crackled as I bit in, buttery and salty, and the cheese melted just enough to stretch. We sat near the entrance watching travelers pass, and for a moment, the city felt small enough to hold in one hand.
What I Loved Most: That mix of motion and pause—how Chicago lets you move quickly but rewards you when you slow down.
My highlights? The U.S. Pizza Museum was playful and nostalgic, full of old menus, delivery bags, and pizza-themed everything. I laughed more than I expected. Later, we wandered to Pleasant House Bakery in Pilsen, where I ordered a steak and ale pie. The crust was golden and sturdy, the filling rich with rosemary and gravy. It came steaming and fragrant, served with a little jar of house-pickled vegetables. It felt like something a grandmother might make if she trained as a chef.
After lunch, we strolled the Fulton River District, where murals broke up the gray brick with splashes of color and bold outlines. I liked how the city tucked beauty into alleys and overpasses—never showy, always present.
Plan your Chicago trip:
- Drive Time from Milwaukee: ~1.5 hours south; or fly into O’Hare or Midway
- Vibe: Energetic, layered, modern with historic roots
- Best For: Food lovers, architecture fans, art-seeking weekenders
- Lodging: The Blackstone, The Publishing House B&B, or a boutique hotel in the Loop
- Dining: Chicago French Market, Pleasant House Bakery, The Purple Pig
- Activities: U.S. Pizza Museum, Riverwalk, Art Institute, French Market, lakefront biking, mural walks
- Best Time to Visit: Late spring and early fall for mild temps and city festivals
Galena, Illinois: Time Travel with Cobblestones and Charm
Galena felt like stepping into a painting—sloping streets, brick storefronts, and church steeples rising above tree-lined hills. I turned to my husband and said, “It’s like the past never left, it just slowed down.”
We walked through downtown where every window seemed to hold something handmade: soaps, quilts, old books, truffles. The sidewalks curved with the land, and even the air felt calmer. I loved how history wasn’t presented in plaques—it was baked into the streets, the staircases, the way people lingered over coffee on a cool morning.
What I Loved Most: Galena didn’t rush you. It offered beauty in the details—a doorknob, a railing, a long view down the river at dusk.
My highlights? Breakfast at Otto’s Place. I ordered the sweet potato pancakes with cinnamon butter and thick-cut bacon. The pancakes were soft and slightly crisp at the edges, warm and fragrant with spice. The maple syrup soaked in slowly, and the bacon added just the right salt. We sat by the window, watching the day come alive one antique shop at a time.
Plan your Galena trip:
- Drive Time from Chicago: ~3 hours west
- Vibe: Historic, quiet, romantic
- Best For: Couples, antique hunters, peaceful wanderers
- Lodging: B&Bs in 19th-century homes, riverside inns, cozy cottages
- Dining: Otto’s Place, Fried Green Tomatoes, Log Cabin Steakhouse
- Activities: Main Street shopping, Ulysses S. Grant Home, hiking Horseshoe Mound Preserve, wine tastings
- Best Time to Visit: Fall for foliage, or spring for blooms and fewer crowds
Bloomington, Illinois: Courthouse Squares and Prairie Calm
Bloomington is kind of town where you can hear your own thoughts again. As we drove in, the streets opened up and the land flattened in that peaceful Midwestern way. I looked out at the horizon and said to my husband, “Let’s not fill every hour. Let’s just follow what feels good.”
We wandered around the courthouse square downtown, where old brick buildings held bookstores, cafés, and shops with creaky wood floors. People waved when they passed. There was a stillness in the alleys, a rhythm in the window displays. The town was welcoming.
What I Loved Most: Bloomington had a quiet sturdiness. You could feel its roots in every block.
My highlights? Brunch at The Coffee Hound. I ordered the egg sandwich with roasted red pepper aioli and cheddar on sourdough, and a lavender latte that smelled like spring. The eggs were soft, the bread grilled just enough to crisp, and the sauce tied it all together with heat and depth. The café buzzed with students and locals, but it still felt cozy. We stayed long after the plates were cleared.
I thought I would enjoy living here. But then I remembered that winters are very harsh here. Wind cuts across the flatland and makes you want to stay inside.
Plan your Bloomington trip:
- Drive Time from Chicago: ~2 hours southwest
- Vibe: Steady, relaxed, rooted in tradition
- Best For: Small-town explorers, quiet weekends, history lovers
- Lodging: Vrooman Mansion, local inns, or classic downtown stays
- Dining: The Coffee Hound, Epiphany Farms, Anju Above
- Activities: David Davis Mansion, Constitution Trail, downtown galleries, local theater
- Best Time to Visit: Late summer or early fall for farmers markets and fair weather
Champaign, Illinois: Campus Calm and Creative Corners
Champaign felt grounded—like a place that knew how to balance curiosity and comfort. The University buzzed with quiet energy, but the streets around it were soft-spoken. I told my husband, “Let’s take our time. This town doesn’t seem in a hurry, and neither are we.”
We wandered through the downtown square where murals bloomed on brick walls and shops carried everything from vinyl records to handmade chocolate. There was music floating somewhere—maybe from a bar patio, maybe just from someone’s window. It made the sidewalks feel warm.
What I Loved Most: The way Champaign lets art and intellect live side by side. It didn’t perform for us—it just was.
My highlights? Brunch at The Literary. I ordered the breakfast sandwich on focaccia with herb eggs, thick bacon, and a sharp white cheddar that melted just right. The bread was golden, warm, and faintly garlicky, and the café smelled like roasted coffee and paperbacks. We ate slowly, then browsed the shelves for books we didn’t need but couldn’t leave behind.
Plan your Champaign trip:
- Drive Time from Chicago: ~2.5 hours south
- Vibe: Intellectual, laid-back, artsy with a Midwestern backbone
- Best For: Couples, quiet creatives, small-city explorers
- Lodging: Local inns, downtown boutiques, or stays near campus
- Dining: The Literary, Watson’s Shack & Rail, Maize Mexican Grill
- Activities: Krannert Art Museum, downtown murals, campus walks, Curtis Orchard in fall
- Best Time to Visit: Spring and early fall for mild weather and student energy
Schaumburg, Illinois: Quiet Comfort Just Outside the Rush
Schaumburg gave us space—wider streets, tall trees, and the kind of suburban calm that makes you exhale without noticing. After the hum of the city, I said to my husband, “Let’s not rush. Let’s just let the day find us.”
We spent the morning at the Spring Valley Nature Center, walking the shaded trails where birdsong echoed and wildflowers grew in soft clusters. It felt like stepping into a quiet pocket of the Midwest—unbothered, gentle, and still. Later, we wandered into the Woodfield Mall, where the energy picked up. Even there, something about the town’s pace kept it grounded.
What I Loved Most: Schaumburg blended convenience with ease—like a town that knew how to hold both comfort and curiosity.
My highlights? Lunch at Chicago Culinary Kitchen. I had the brisket sandwich with burnt ends and a side of smoked elote. The meat fell apart with a fork, kissed with spice and hickory. The corn was rich, creamy, and just a little charred—brightened by lime and cotija. We sat at a picnic table near the window, the scent of smoke clinging to the air like memory.
Plan your Schaumburg trip:
- Drive Time from Chicago: ~45 minutes northwest
- Vibe: Comfortable, family-friendly, surprisingly green
- Best For: Relaxed weekenders, suburban explorers, shoppers and walkers
- Lodging: Hotel at the Renaissance Schaumburg, boutique stays, and classic chains
- Dining: Chicago Culinary Kitchen, Pilot Pete’s, Lou Malnati’s
- Activities: Spring Valley Nature Center, Woodfield Mall, LEGOLAND Discovery Center, local breweries
- Best Time to Visit: Spring or fall for cool trails and pleasant walks
Naperville, Illinois: Riverwalks and Small-Town Ease
Naperville felt balanced—big enough to wander, small enough to feel familiar. I told my husband, “It’s the kind of place where you could lose track of time and not mind.” The town wrapped around us gently, full of cafes, fountains, and friendly nods.
We spent most of our morning along the Riverwalk, where the DuPage curved quietly past brick paths and flowerbeds. We are used to the charming Riverwalks in San Antonio and Boerne close to our home in Texas. But Naperville Riverwalk was truly a hidden gem.
Ducks floated under footbridges, and children ran along the stones in bare feet. There were spots to sit, spots to think, and spots to just listen to the water. It was the kind of calm that settled in slowly.
What I Loved Most: Naperville made space for stillness without ever feeling sleepy. There was movement, but no rush.
My highlights? Brunch at Egg Harbor Café. I had the farmers market skillet—roasted sweet potatoes, kale, zucchini, eggs just right, and a side of cranberry orange muffins still warm from the oven. The whole place smelled like maple and coffee. I remember the first bite of muffin—crumbly, citrus-bright, soft in the middle—and thinking, “We could stay here a while.”
Plan your Naperville trip:
- Drive Time from Chicago: ~45 minutes west
- Vibe: Cozy, polished, walkable
- Best For: Couples, weekenders, suburban explorers
- Lodging: Hotel Indigo, Harrison House B&B, boutique stays near downtown
- Dining: Egg Harbor Café, Sullivan’s Steakhouse, Le Chocolat du Bouchard
- Activities: Riverwalk, Naper Settlement, Naperville Art League, independent bookstores
- Best Time to Visit: Spring through fall for festivals and sunny strolls
Rockford, Illinois: Quiet Corners and Garden Paths
Rockford surprised me. It didn’t shout—it welcomed. The pace felt gentle, the spaces wide open. As we pulled into town, I looked out at the Fox River glinting through the trees and said, “Let’s not plan too much. Let’s just let the day unfold.”
We began at Anderson Japanese Gardens. The paths curved softly around ponds and stone lanterns. I heard my own footsteps, the rustle of leaves, the distant splash of a koi. I didn’t want to leave. It felt like a place built for stillness. From there, we made our way downtown where old warehouses had become galleries and bakeries, and people smiled when they passed by.
What I Loved Most: Rockford let us move slowly without feeling like we were missing anything. Every corner had a quiet purpose.
My highlights? Lunch at Fresco at the Gardens. I ordered the avocado toast with smoked salmon and a side of roasted potatoes. The bread was thick and warm, the avocado creamy, the salmon just salty enough. There was dill, lemon, and cracked pepper, and everything tasted fresh—like it had been plated with care, not speed. We sat near the window and watched a family of ducks wander past.
Plan your Rockford trip:
- Drive Time from Chicago: ~1.5 hours northwest
- Vibe: Serene, local, under-the-radar
- Best For: Garden lovers, art seekers, couples wanting a slower day
- Lodging: Riverview Inn & Suites, boutique Airbnbs, or nearby B&Bs
- Dining: Fresco at the Gardens, Abreo, Lino’s
- Activities: Anderson Japanese Gardens, Rockford Art Museum, Nicholas Conservatory, Riverwalk
- Best Time to Visit: Spring for blooms, fall for quiet charm
Leaving Illinois: What Stayed With Me
By the time we left Illinois, I’d stopped trying to pick a favorite. Each town had its own shape—its own voice. A garden path in Rockford. A lemon scone in Evanston. A shaded bench along the Mississippi in Alton. They came together like chapters in a book I didn’t know I’d needed to read.
If you're looking for places that invite you to slow down and look around, Illinois holds them gently. It’s not always about what’s on the map—it’s what lingers after you’ve gone. And I’m already thinking about the next page.
Jump to a Spot...
- • Springfield, Illinois: Lincoln’s Legacy and Small-Town Pride
- • Chicago, Illinois: Markets, Murals, and Morning Heat
- • Galena, Illinois: Time Travel with Cobblestones and Charm
- • Bloomington, Illinois: Courthouse Squares and Prairie Calm
- • Champaign, Illinois: Campus Calm and Creative Corners
- • Schaumburg, Illinois: Quiet Comfort Just Outside the Rush
- • Naperville, Illinois: Riverwalks and Small-Town Ease
- • Rockford, Illinois: Quiet Corners and Garden Paths
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