Romantic Weekend Getaways in Illinois
Plan a weekend trip to one of these beautiful inns to relax with spa treatments, great food and wine tasting.
Illinois has a quiet way of revealing its charm, one historic inn, vineyard suite, or lakeside escape at a time. Whether you’re wandering cobblestone streets in Galena, savoring a French dinner in Homewood, or cozying up at a golf resort in Glenview, the state offers a variety of romantic getaways that feel both close to home and worlds away. I remember thinking, "We don’t always need to travel far to feel completely transported." Each place held space for connection, whether it was a grand gesture or a simple shared meal.
Best Romantic Weekend Getaways in Illinois:
Goldmoor Inn - 2 hours 45 minutes from Chicago, Illinois
We drove about 3 hours west (165 miles) from Chicago to Galena (population around 3,200), a riverfront town once booming with lead mining and steamboats. More than 85% of its buildings are on the National Register of Historic Places. We strolled down Main Street lined with 19th-century brick storefronts, toured Ulysses S. Grant’s home, and capped the evening with dinner in a converted warehouse along the Galena River.
Perched above the Mississippi River with sweeping views and quiet grace, the Goldmoor Inn in Galena felt like stepping into a romantic dream. The turret suites, the in-room fireplaces, and the gentle hush of the countryside all came together like a love letter in motion. I remember thinking, “This is the kind of place you don’t want to leave, not just because it’s beautiful, but because it feels like it knows you.”
What I Loved Most: Soaking in a whirlpool tub while watching the sun set through arched windows, the softest music playing and time standing still.
My highlights? A candlelit dinner at the inn’s restaurant, pan-seared duck breast with wild mushroom risotto, paired with a glass of velvety Pinot Noir. Every bite was rich with flavor and perfectly timed with the view beyond the windows.
The trade-off? Goldmoor Inn’s secluded setting made spontaneous dinners out a bit tricky.
Travel Tips:
- Location: 9001 N Sand Hill Rd, Galena, IL 61036
- Vibe: Romantic, refined, secluded
- Best For: Couples celebrating an anniversary or honeymoon
- Amenities: Suites with whirlpool tubs, spa services, on-site fine dining, private patios
- Cost: $$$ – Rates from ~$300/night
- Tip: Reserve a turret suite for the best views and ultimate privacy
The Deer Path Inn
We drove about 45 minutes north (35 miles) from downtown Chicago to Lake Forest (population around 19,000), one of the North Shore’s most historic communities. Founded in 1857 as a lakeside retreat, the town is known for its tree-lined streets, grand estates, and Lake Forest College’s leafy campus.
Staying at The Deer Path Inn in Lake Forest was like being whisked away to the English countryside, without leaving Illinois. From the Tudor-style architecture to the roaring fireplaces and polished service, everything felt steeped in elegance and storybook romance. I remember thinking, “This is how it must feel to live inside a fairytale.”
What I Loved Most: An evening stroll through the garden courtyard, followed by cocktails in the pub, made us feel like the outside world had completely disappeared.
My highlights? Dinner in The English Room, filet medallions with port wine reduction and truffle mashed potatoes. The dim lighting, soft music, and white-gloved service made it a meal to remember.
If I had to nitpick… The pub and dining rooms were bustling rather than intimate on my weekend there.
Travel Tips:
- Location: 255 E Illinois Rd, Lake Forest, IL 60045
- Vibe: Sophisticated, old-world charm, upscale
- Best For: Couples seeking luxury and history wrapped in one
- Amenities: Fine dining, English pub, luxurious suites, elegant gardens
- Cost: $$$ – Rates from ~$350/night
- Tip: Reserve afternoon tea in the English Room, it’s as delightful as it sounds
La Banque Hotel, Homewood
We drove about 35 minutes south (25 miles) from downtown Chicago to Homewood (population around 19,300). Once a stop along the Illinois Central Railroad, Homewood grew into a classic South Suburb with tree-lined streets and a lively downtown.
La Banque Hotel made us feel like we’d discovered a slice of Europe tucked into the heart of Homewood, Illinois. Housed in a beautifully restored former bank, this boutique hotel blended timeless charm with luxurious ease. I remember thinking, “It’s amazing how a place can feel so familiar and so indulgent all at once.” From the marble floors to the arched windows and curated artwork, every detail told a story of thoughtful restoration and romance.
What I Loved Most: Curling up in the lounge with a glass of wine and soft jazz playing in the background, just the two of us, no rush, no distractions.
My highlights? Dinner at La Voute Bistro + Bar, the hotel’s in-house French restaurant. I had the duck confit served with whipped potatoes and haricot verts, finished with a citrus glaze that was perfectly balanced. We shared a crème brûlée for dessert that cracked like glass and melted in our mouths.
One thing to keep in mind: Downtown Homewood had limited nightlife options within walking distance.
Travel Tips:
- Location: 2034 Ridge Rd, Homewood, IL 60430
- Vibe: Intimate, refined, European-inspired
- Best For: Couples looking for elegance and cultural charm
- Amenities: Boutique rooms, onsite French restaurant, art gallery, fitness center
- Cost: $$ – Rates from ~$180/night
- Tip: Book a couples’ package and don’t miss brunch at La Voute
The Glen Club, Glenview
We drove about 35 minutes northwest (20 miles) from downtown Chicago to Glenview (population around 48,000). Once a quiet farming community, Glenview grew rapidly after WWII and still balances suburban charm with cultural spots.
The Glen Club offered a quiet kind of luxury, wrapped in the manicured greens of its championship golf course and the peaceful rhythm of Glenview. Staying here felt like stepping into a slower, more graceful world. I remember thinking, “Everything here is designed to make you breathe a little deeper.” From the sweeping views of the fairways to the soft elegance of our room, it was the perfect balance of retreat and refinement.
What I Loved Most: Sitting on the terrace at sunset, glasses clinking, the fairway bathed in golden light, it felt like we had the whole place to ourselves.
My highlights? Dinner at the Club’s elegant dining room. I had the filet mignon with truffle mashed potatoes and grilled asparagus, paired with a bold red wine that lingered just right. It was a simple meal made exceptional by the view, the service, and the company.
Less perfect? My weekends felt dominated by a tournament crowd.
Travel Tips:
- Location: 2901 W Lake Ave, Glenview, IL 60026
- Vibe: Elegant, tranquil, golf-resort charm
- Best For: Romantic weekends, special occasions, golf lovers
- Amenities: Golf course, fine dining, private terraces, banquet rooms
- Cost: $$$ – Rates from ~$250/night
- Tip: Ask for a lake-view room for a stunning morning surprise
A Night at The Blackstone
The Blackstone felt like stepping into a quieter kind of luxury, the kind that hums low and steady, with velvet chairs, marble floors, and city stories tucked into the walls. I walked into the lobby, looked up at the stained-glass dome, and whispered, “We picked the right place.”
Our room faced Grant Park. Past the wide windows, the lake shimmered under a gray sky, and I could hear the occasional hum of the L in the distance. The building creaked in the comforting way old buildings do, timeless, not tired. We dropped our bags and didn’t speak for a while. Just let the stillness settle in after the rush of Michigan Avenue.
What I Loved Most: The way The Blackstone made the city feel close, but not loud. It offered a pause between moments, a place to catch my breath. I also loved that you can bring your dog.
My highlights? Breakfast downstairs at Mercat a la Planxa. I had the tortilla Española with manchego and roasted onions, served warm beside a small, sharp salad and thick coffee. The egg was custardy and rich, the cheese just starting to melt, the onions sweet as jam. The scent of paprika and olive oil lingered long after the plates were cleared.
One downside? The location along Michigan Avenue came with city noise at night.
Plan your stay at The Blackstone:
- Location: 636 S Michigan Ave, across from Grant Park
- Vibe: Historic glamour meets modern boutique comfort
- Best For: Couples, architecture lovers, weekend city escapes
- Nearby: Art Institute of Chicago, Lakefront Trail, Buckingham Fountain, Museum Campus
- Dining: Mercat a la Planxa, The Dearborn, Lou Malnati’s nearby
- Best Time to Visit: Spring and fall for cooler walks and lake views
Harvey House Bed and Breakfast - 15 min from Chicago
We drove about 20 minutes west (10 miles) from downtown Chicago to Oak Park (population around 54,000). This historic suburb is best known as the hometown of Frank Lloyd Wright, whose Prairie-style designs still line the streets. We toured Wright’s Home and Studio, admired Unity Temple, and strolled past rows of landmark houses before capping the day with dinner along Marion Street in the buzzing downtown district.
Harvey House Bed and Breakfast felt like walking into someone’s dream of comfort. Nestled in Oak Park, it wrapped us in warm hospitality and timeless elegance the moment we arrived. The crackle of the fireplace, the rich wooden accents, the clawfoot tubs, it all whispered relaxation. I remember thinking, “This is the kind of place that holds you, heart and all.” It was romantic in the most peaceful, effortless way.
What I Loved Most: Waking up to the scent of coffee and cinnamon, slipping into a robe, and enjoying breakfast by the fire without ever needing to leave the house.
My highlights? The morning spread of lemon-ricotta pancakes topped with berries, crispy bacon, and French-pressed coffee was perfection. Homemade, beautifully presented, and soul-warming.
Travel Tips:
- Location: 107 S Scoville Ave, Oak Park, IL 60302
- Vibe: Cozy, upscale, romantic hideaway
- Best For: Couples who love timeless elegance and gourmet breakfasts
- Amenities: Fireplaces, jetted tubs, homemade breakfast, walkable location
- Cost: $$ – Rates from ~$200/night
- Tip: Choose the Bungalow Suite for extra privacy and a two-person spa tub
Affordable Couples' Weekend at Inn at 835, Illinois
Instead of driving, we caught Amtrak’s Lincoln Service from Union Station in Chicago, a smooth 3.5-hour ride (about $20–$30) that drops you right downtown. The train rolled past farms and prairies, setting a relaxed tone. Once there, we toured the Abraham Lincoln Presidential Library and Museum, browsed local shops near the Old Capitol Plaza, and ended the evening with a quiet stroll past 19th-century brick buildings glowing under the lamplights.
The Inn at 835 transported us to another era, refined, elegant, and unhurried. Located in historic Springfield, it offered quiet charm and thoughtful touches that made us feel like cherished guests. I remember thinking, “This is where romance lives, in the pause between check-in and check-out.” The tall ceilings, antique furnishings, and vintage character added an old-world romance to every moment.
What I Loved Most: Sipping wine in the garden courtyard under string lights as the world slowed to a hush.
My highlights? A charcuterie board and glasses of red wine served in the parlor lounge, simple and cozy, with just enough indulgence.
Travel Tips:
- Location: 835 S 2nd St, Springfield, IL 62704
- Vibe: Historic, quiet, genteel
- Best For: Couples who enjoy classic architecture and Southern-style hospitality
- Amenities: Suites with whirlpool tubs, breakfast, garden, walkable to historic downtown
- Cost: $$ – Rates from ~$150/night
- Tip: Take the free bikes for a charming ride around Washington Park
Cloran Mansion Bed & Breakfast - 2 hours and 45 minutes
Set in the rolling hills of Galena, Cloran Mansion Bed & Breakfast felt like something from a storybook. The stone turret, stained glass, and ivy-covered walls whispered of history and heart. I remember thinking, “This is the kind of place where love lingers in the walls.” From the moment we stepped inside, it was all about warmth, welcome, and escape.
What I Loved Most: Watching snowflakes fall outside while soaking in the heart-shaped whirlpool tub with candlelight flickering nearby.
My highlights? A decadent breakfast of baked French toast with maple glaze, crispy sausage, and fresh-squeezed orange juice. It tasted like comfort and care.
The catch? Galena’s popularity meant the surrounding area was packed on my weekend there.
Travel Tips:
- Location: 1237 Franklin St, Galena, IL 61036
- Vibe: Romantic, historic, whimsical
- Best For: Couples seeking peace, pampering, and small-town charm
- Amenities: Fireplaces, whirlpool tubs, gardens, homemade breakfast
- Cost: $$ – Rates from ~$160/night
- Tip: Ask for the Tower Room for the full mansion experience
The Davie School Inn - 5 hours from Chicago
We drove about 2 hours southeast (120 miles) from St. Louis to Anna (population around 4,000), a quiet town in Union County. Founded in the mid-1800s and once a railroad stop, Anna still has a traditional town square and a slower pace of life. We explored downtown with its historic storefronts, stopped into a local diner for pie and coffee, and capped the evening with a stroll through the shaded streets as church bells rang.
Turning an old schoolhouse into a boutique inn? It sounds quirky, and it is, in all the best ways. The Davie School Inn in Anna, Illinois, was unexpected, full of character, and deeply charming. I remember thinking, “We’ve never stayed anywhere quite like this.” The rooms were huge, the ceilings high, and the vibe somewhere between nostalgic and luxurious. It was playful and romantic at once.
What I Loved Most: The blackboard still hung on the wall in our suite, reminding us of simpler days while we lounged in complete comfort.
My highlights? A full country breakfast delivered to our room: scrambled eggs with garden herbs, thick-cut bacon, pancakes, and fresh fruit. It was like home, but elevated.
Travel Tips:
- Location: 300 Freeman St, Anna, IL 62906
- Vibe: Eclectic, nostalgic, relaxed
- Best For: Couples seeking something different with a touch of whimsy
- Amenities: Oversized suites, breakfast delivery, Jacuzzi tubs, historic charm
- Cost: $$ – Rates from ~$170/night
- Tip: Bring a bottle of wine and enjoy a quiet night in with the original classroom blackboard as your backdrop
Plan Your Romantic Escape
Whether you're toasting under the stars at a countryside bed and breakfast or exploring a historic downtown hand-in-hand, Illinois delivers unforgettable romantic weekends. From the boutique luxury of La Banque Hotel to the castle-like charm of Goldmoor Inn, each of these stays brings its own unique atmosphere, wrapped in warmth, elegance, and the kind of moments you’ll want to revisit again and again.
Booking Checklist
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