Romantic Weekend Getaways in Illinois

Illinois offers some of the best romantic weekend getaways in the Midwest, and it’s become one of my favorite states for couples looking to mix city excitement with peaceful escapes. I’ve been covering getaways in Illinois for 30 years, which makes me a true local expert.

Whether you’re sharing a night out in the best restaurants of Chicago, exploring the unique history of Galena, or discovering the underrated charm of Starved Rock’s hiking trails, Illinois has plenty of destinations made for two. That’s why these spots rank among the best romantic trips in the Midwest, and why they’ve become some of my favorite getaway recommendations.

The best part is the variety: world-class dining, cozy small towns, and beautiful natural parks. Think evenings enjoying the best live jazz, wine tastings in unique vineyards, or watching sunsets over the Mississippi River. These details are what make Illinois’s romantic escapes both unique and some of the best experiences for couples.

With destinations just a few hours apart, it’s easy to plan the best kind of weekend whether you want city lights or country charm. Whether you’re after relaxation, adventure, or a little of both, Illinois offers the best settings to spark romance.

Which Illinois escape will you choose? If you’re searching for the best mix of scenery, intimacy, and memorable moments, these weekend getaways deliver. They’re not just trips, they’re the best, sometimes underrated, always unique, and forever some of my favorite Midwest escapes.

Best Romantic Weekend Getaways in Illinois:

Goldmoor Inn - 2 hours 45 minutes from Chicago, Illinois

We drove about 3 hours west from Chicago to Galena , 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.

I felt such a magical sense of seclusion the moment I arrived at Goldmoor Inn, tucked along the bluffs of the Mississippi River with sweeping views that immediately took my breath away.

I loved how my suite felt both elegant and cozy, with a fireplace, whirlpool tub, and private balcony, and my favorite part was watching the sunset over the river from that perfect perch.

I enjoyed the gourmet breakfast delivered right to my door each morning—it was such a joyful way to start the day without ever leaving the comfort of my room.

I treated myself to dinner at the on-site restaurant, where every dish felt crafted with care and paired beautifully with the serene atmosphere, making it the coolest dining experience in Galena.

I appreciated the little luxuries like plush robes, fresh flowers, and thoughtful touches throughout the inn that made my stay feel both personal and indulgent.

I also spent time exploring the nearby town of Galena, with its charming shops and historic streets, but I always looked forward to returning to the inn’s peaceful embrace.

I found the property’s location perfect for a romantic getaway, though it also felt welcoming enough for a relaxing solo retreat where I could recharge in style.

I liked ending my evenings by the fire with a glass of wine, listening to the quiet of the river valley all around me.

I left knowing Goldmoor Inn was a brilliant idea for anyone seeking elegance, comfort, and unforgettable river views in one spectacular setting.

Check prices at Goldmoor Inn.

The Deer Path Inn

We drove about 45 minutes north from downtown Chicago to Lake Forest, 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.

I felt transported the moment I stepped into The Deer Path Inn, with its English Tudor style and old-world charm that gave my stay a magical sense of history and tradition.

I loved how my room felt like a private retreat, with elegant furnishings, a cozy fireplace, and a spa-like bathroom, and my favorite detail was the plush bed that made every night’s sleep incredibly restful.

I spent time in the inn’s stunning courtyard garden, sipping tea surrounded by blooming flowers and ivy-covered walls, and it felt like the coolest hidden escape right in the heart of Lake Forest.

I enjoyed dining at the White Hart Pub, where the menu offered hearty classics in a warm and lively setting, and it was such a joyful place to unwind in the evenings.

I also treated myself to a fine dining experience at The English Room, where the refined atmosphere and exquisite dishes made dinner feel truly special.

I appreciated the inn’s thoughtful touches—afternoon tea service, attentive staff, and cozy nooks throughout the property—that made the entire experience feel personal and inviting.

I liked exploring the nearby shops, lakefront, and historic streets of Lake Forest during the day, knowing I had such a romantic and welcoming retreat to return to.

I ended each night with a glass of wine by the fireplace, reflecting on how relaxed and content I felt in such a timeless setting.

I left knowing The Deer Path Inn was a brilliant idea for anyone craving European elegance blended with Midwestern warmth in one unforgettable stay.

Check prices at The Deer Path Inn

La Banque Hotel, Homewood

We drove about 35 minutes south from downtown Chicago to Homewood. Once a stop along the Illinois Central Railroad, Homewood grew into a classic South Suburb with tree-lined streets and a lively downtown.

I felt such a magical sense of surprise when I walked into La Banque Hotel in Homewood, with its restored 1920s bank building transformed into a boutique hotel full of elegance and charm.

I loved how the historic details were preserved—vault doors, marble floors, and soaring ceilings—while blending seamlessly with modern design, and my favorite part was how unique every corner of the property felt.

I stayed in a stylish room with plush bedding, sleek furnishings, and a spa-like bathroom, and it was the coolest combination of old-world character and contemporary comfort.

I enjoyed dining at La Voute, the hotel’s on-site French-inspired restaurant located in the former bank vault, and every meal felt joyful and memorable in such an unusual setting.

I appreciated the intimate atmosphere of the hotel, where the staff made me feel personally welcomed and cared for, creating a stay that felt both polished and warm.

I liked that the location put me right in the heart of Homewood, with walkable shops, cafés, and local culture just outside the door, making the experience both convenient and exciting.

I also found the rooftop terrace to be a brilliant idea—a perfect spot to enjoy a glass of wine while watching the town come alive below.

I ended each evening feeling grateful for the balance of history, style, and comfort that made the hotel stand out in such a unique way.

I left knowing La Banque Hotel was a gem for anyone seeking a boutique stay that blends heritage with modern luxury in the coolest way possible.

Check prices at La Banque Hotel

The Glen Club, Glenview

We drove about 35 minutes northwest from downtown Chicago to Glenview. Once a quiet farming community, Glenview grew rapidly after WWII and still balances suburban charm with cultural spots.

I felt an immediate sense of elegance when I arrived at The Glen Club in Glenview, with its classic clubhouse architecture and beautifully landscaped grounds that created a magical first impression.

I loved how my guest room overlooked the championship golf course, and my favorite moments were spent sipping coffee on the balcony while taking in the sweeping green views.

I enjoyed playing a round of golf on the Tom Fazio–designed course, which was both challenging and exciting, surrounded by rolling fairways and peaceful scenery.

I also treated myself to dinner at the on-site restaurant, where the refined atmosphere and creative dishes made every meal feel special and joyful.

I liked that the property felt private and peaceful, making it an ideal romantic getaway, yet it was close enough to Chicago to combine relaxation with city adventures.

I appreciated the little details in the guest rooms—plush bedding, elegant décor, and spa-like bathrooms—that made my stay feel polished and comfortable.

I found the staff to be warm and attentive, adding a personal touch that made me feel completely taken care of during my stay.

I ended my evenings enjoying the lounge, where the relaxed setting was the coolest place to wind down with a cocktail after a day outdoors.

I left knowing The Glen Club was a brilliant idea for anyone looking for a gem of a retreat that combines luxury accommodations, fine dining, and championship golf in one unforgettable setting.

Check prices at The Glen Club

A Night at The Blackstone

I felt a magical sense of grandeur the moment I stepped into The Blackstone in Chicago, with its historic Beaux-Arts architecture and lobby filled with timeless details that made me feel part of the city’s story.

I loved how my room blended historic charm with sleek modern touches—plush bedding, curated art, and views of Grant Park and Lake Michigan—and my favorite part was watching the city lights sparkle at night from my window.

I enjoyed wandering the hotel’s hallways lined with artwork, which gave the whole place a cool, gallery-like vibe that felt both sophisticated and unique.

I spent time in the lounge, where cocktails were crafted with care and the lively yet elegant atmosphere made evenings feel joyful and memorable.

I appreciated the location right on Michigan Avenue, which put me steps away from Grant Park, the Art Institute, and the lakefront—it was the absolute best base for exploring Chicago.

I also liked the way the hotel balanced its history with modern luxury, from ornate ceilings and marble floors to tech-friendly guest rooms designed for comfort.

I treated myself to a relaxed breakfast with a view of the park, which became a favorite ritual before heading out to explore the city each day.

I ended each evening feeling grateful for the mix of culture, style, and comfort that The Blackstone delivered so effortlessly.

I left knowing The Blackstone was a brilliant idea for anyone wanting a gem of a stay that captures Chicago’s history while offering all the modern amenities of today.

Check prices at The Blackstone

Harvey House Bed and Breakfast - 15 min from Chicago

We drove about 20 minutes west from downtown Chicago to Oak Park. This historic suburb is best known as the hometown of Frank Lloyd Wright, whose Prairie-style designs still line the streets.

I felt such a magical welcome when I arrived at Harvey House Bed and Breakfast in Oak Park, where the charming exterior and warm hospitality immediately set the tone for my stay.

I loved how each room had its own personality, blending elegant décor with thoughtful details, and my favorite part was the fireplace in my suite that made the space feel extra cozy.

I enjoyed waking up to a homemade breakfast each morning, with fresh ingredients and creative dishes that turned the start of my day into a joyful experience.

I liked that the inn was tucked away in a quiet neighborhood yet still close to downtown Oak Park, where I could explore shops, restaurants, and Frank Lloyd Wright’s famous architecture—it was the coolest mix of peaceful retreat and local adventure.

I appreciated the little touches, like plush robes, soft linens, and a welcoming common area stocked with books and treats, which made the whole stay feel personal and special.

I spent time relaxing in the garden and loved how the outdoor spaces felt like hidden gems, perfect for unwinding with a cup of tea or a glass of wine.

I also found the innkeepers to be incredibly attentive, offering recommendations and ensuring everything about my stay was comfortable and seamless.

I ended each night feeling completely at home, which is rare to find when traveling.

I left knowing Harvey House Bed and Breakfast was a brilliant idea for anyone wanting a unique blend of comfort, charm, and unforgettable hospitality near Chicago.

Check prices at Harvey House Bed and Breakfast

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.

I felt a magical sense of history the moment I walked into the Inn at 835 in Springfield, Illinois, with its grand architecture and vintage details that made me feel like I had stepped back in time.

I loved how my suite combined historic character with modern comforts—ornate woodwork, tall windows, and antique furnishings paired with plush bedding and a spa-like bathroom—and my favorite detail was the private balcony overlooking the neighborhood.

I enjoyed the gourmet breakfast served each morning in the elegant dining room, and it was such a joyful way to start my day before heading out to explore.

I liked wandering the inn’s hallways filled with period décor, which gave the whole place a unique and inviting personality that felt warm and authentic.

I appreciated the location, just steps away from the Illinois State Capitol and downtown Springfield, making it easy to combine relaxation at the inn with exciting local adventures.

I also discovered the inn’s event spaces and gardens, which created a cool and charming backdrop for weddings or gatherings, adding to its versatility.

I spent time relaxing in the parlor, where the cozy atmosphere and timeless design made it the perfect spot to unwind with a book.

I ended each evening feeling grateful for the balance of elegance and comfort that made my stay so memorable.

I left knowing the Inn at 835 was a brilliant idea for anyone seeking a gem of a getaway that blends historic charm, modern amenities, and true Midwestern hospitality.

Check prices at Inn at 835

Cloran Mansion Bed & Breakfast - 2 hours and 45 minutes

I felt such a magical sense of welcome the moment I arrived at Cloran Mansion Bed & Breakfast in Galena, Illinois, with its Italianate architecture and beautifully kept grounds creating an atmosphere of timeless charm.

I loved how my room was filled with cozy details—plush bedding, a fireplace, and a whirlpool tub—and my favorite part was how romantic and peaceful the space felt, perfect for unwinding after a day of exploring.

I enjoyed the homemade breakfast each morning, served with care and fresh ingredients, and it was a joyful way to start the day while chatting with other guests.

I liked strolling the property’s gardens and sitting out in the gazebo, where the quiet surroundings felt like a hidden escape just minutes from Galena’s historic Main Street.

I appreciated how the innkeepers made everything feel personal and welcoming, offering suggestions for local restaurants, wineries, and shops, which made my visit even more exciting.

I also discovered that the inn had a charming cottage option, ideal for a family stay or a more private romantic getaway, which felt like the coolest feature.

I spent my afternoons exploring Galena’s rich history, boutiques, and scenic overlooks, always looking forward to returning to the warm comfort of the mansion.

I ended each evening feeling relaxed and cared for, with the glow of the fireplace adding to the atmosphere.

I left knowing Cloran Mansion Bed & Breakfast was a brilliant idea for anyone looking for a gem of a stay that blends history, comfort, and heartfelt hospitality in Galena.

Check prices at Cloran Mansion Bed & Breakfast

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 felt an unusual mix of history and comfort the moment I arrived at The Davie School Inn in Anna, Illinois, where a former 1910 schoolhouse has been transformed into a charming bed and breakfast.

I loved how each suite was located in a former classroom, with soaring ceilings, hardwood floors, and original chalkboards preserved, and my favorite part was how unique every room felt while still offering modern luxuries.

I enjoyed the spaciousness of my suite, complete with a whirlpool tub, cozy sitting area, and a bed so comfortable that every night’s sleep felt magical.

I liked the hearty homemade breakfast delivered right to my room each morning—it was such a joyful way to begin the day without ever having to leave my cozy space.

I appreciated how the inn combined its rich history with personal hospitality, making the whole stay feel both cool and meaningful.

I spent my afternoons exploring the Shawnee Hills Wine Trail and nearby state parks, always glad to return to the relaxing atmosphere of the inn afterward.

I also enjoyed the little details throughout—historic memorabilia, welcoming common areas, and the sense of nostalgia that came with staying in a schoolhouse reimagined for comfort.

I found it equally perfect for a romantic getaway or a family retreat, with spacious suites and a setting that felt both private and inviting.

I left knowing The Davie School Inn was a brilliant idea for anyone seeking a gem of a stay that blends history, comfort, and unique character in southern Illinois.

Check prices at The Davie School Inn

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.

Hi, I'm Ema. Ready to plan your next weekend getaway? Let me help. I have 30 years of experience, over 400,000 social media followers and I've been featured as a travel expert on abc6 Morning Show, Best of the Web, USAToday, and many other media outlets, government and educational institutions. When I'm not traveling around the USA, I live in Austin, TX with my husband and son. Click for more.

 

Leave a Comment