Romantic getaways are a must for all couples, no matter how much you love your hometown of the Windy City.

Whether you choose a day trip in the Midwest or a weekend getaway by plane, the best romantic getaways transport you from the everyday routine to a memorable intimate escape.

Destinations await where you'll find balance together, share experiences, and create new memories.

Quick Answer Guide to 9 Romantic Getaways From Chicago

‌Romantic Day Trips From Chicago‌

‌Weekend Getaways for Couples From Chicago‌

‌Best Couples Getaways From Chicago‌

Romantic Day Trips From Chicago

The best romantic day trips from Chicago are getaway spots close enough to be a two-hour drive.

Whether you barely approach the Illinois border or venture into another state, having limited time for an adventure won't limit the relaxed vibes, picturesque scenery, and thoughtful romance you'll find in these destinations.

1. Lake Geneva, Wisconsin

‌How to Get to Lake Geneva‌

Driving to Lake Geneva from Chicago is an easy 90 minutes, whichever way you go. Take the Dan Ryan (I-90W/I-94W) to the Tri-State Tollway (I-294N), then to WI-50/75th Street.

You can also take the Eisenhower (I-290) to Route 12 and take that right into Lake Geneva.

‌Things to Do in Lake Geneva‌

Geneva Lake is the stunning centerpiece of this romantic weekend getaway, with plenty of outdoor activities on or near the lake. Take in the sun at Big Foot Beach State Park in the summer, or enjoy snowshoeing and cross-country skiing in the winter.

Enjoy a romantic lake tour on Lake Geneva Cruise Lines while eating brunch or dinner or enjoying jazz and cocktails.

Hike the Geneva Lake Shore Path for an up-close view of lakefront architecture and gardens. Many of the estates were built in the 19th century by some of Illinois' wealthiest industrialists. The full path is 26 miles, so pick up a map and decide how much you want to conquer before a romantic dinner or drink at one of more than 30 spots in the charming downtown within walking distance of the trail.

‌Where to Stay in Lake Geneva‌

Depending on your idea of romance, Lake Geneva has accommodations to fit the bill. Camp at Big Foot Beach State Park or book your own idyllic spot smack in the heart of downtown, like this intimate studio Airbnb on Main Street.

Airbnb intimate studio Wisconsin Book Now

Want something a bit more swank? I love Grand Geneva Resort & Spa because it has everything a twosome needs to relax, recharge and indulge. Spa treatments, indoor and outdoor swimming pools, upscale dining, a private 20-acre lake with a scenic walking path, and guest rooms with all the amenities.

Grand Geneva Resort & Spa US Book Now

2. Madison, Wisconsin

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‌How to Get to Madison‌

It takes about two and a half hours by car from Chicago to Madison. Take I-90 W to US-12 W/US-18 W. Follow the signs for John Nolen Drive and cross Monona Bay into Madison.

A flight from O'Hare to Dane County Regional Airport takes about an hour and lands 15 minutes outside downtown.

If you want to pit-stop in Milwaukee, take I-94W from Chicago to E St. Paul Ave. in Milwaukee, then take I-794 onto I-94W into Madison.

‌Things to Do in Madison‌

Madison makes food lovers' lists for a bunch of reasons, from the fabulous Saturday on the Square farmers market to the impressive and varied array of restaurants and bars. Get in on a guided food adventure with Madison Eats Food Tours or Madison Food Explorers, or stroll the square and discover your own romantic spot.

Start the day at indie Coffee for a perfectly prepared cortado and waffle before heading to Olbrich Botanical Gardens to stroll through its 16 acres of beauty. Or wander onto Madison's State Street in the historic downtown for the many unique boutiques.

Make time for the lakes! Madison has five of them, with plenty of parks, beaches, cruises, and waterfront restaurants to take in.

‌Where to Stay in Madison‌

The Governor's Mansion Inn is a stately landmark boutique hotel with five elegant guest rooms on Lake Mendota, walking distance from downtown Madison. While you won't find a whirlpool tub here, the building is part of modern plumbing history! Wisconsin Governor Walter Kohler Sr. installed the original Kohler bathtub in the mansion. The inn's Airbnb listing has excellent photos of what you can expect.

Airbnb unit Madison Book Now

For couples wanting to get fancy with their romantic getaway, the historic downtown Edgewater Hotel is elegant, posh, urban, and right in the middle of everything. The lake views and sunsets are stellar, and spa services are top-notch.

Edgewater Hotel Madison Book Now

3. Indiana Dunes, Indiana

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‌How to Get to Indiana Dunes‌

A short 32-mile drive from Chicago, Indiana Dunes can be reached in under an hour via I-90 E to US-12 E/ Dunes Highway. Get off at N County Line Road and look for signs to lead you to the dunes.

‌Things to Do in Indiana Dunes‌

Indiana Dunes State Park is 15,000 acres of sandy dunes, woodlands, prairies, and marsh. Couples who love to hike, bike, bird watch, and camp will have no shortage of outdoor activities to run off to.

Serene and beautiful Porter Beach on the shore of Lake Michigan offers sparkly clean waters and views of the Chicago skyline. It's a great place to catch a romantic lake sunset.

The nearby locales of Chesterton and Valparaiso are fantastic for small-town exploration. Chesterton's European Market's food, art, entertainment, and the award-winning Lucrezia Cafe make you feel far from the Midwest. Stop in Valparaiso for quaint shops, the Central Park Plaza farmers' market, and the romantic garden walks of the Gabis Arboretum.

‌Where to Stay in Indiana Dunes‌

The Songbird Prairie Bed & Breakfast is a must-stay in nearby Valparaiso, tucked into the countryside about 13 miles from the Indiana Dunes. Gorgeous grounds, cozy-but-elegant rooms, breakfasts made from scratch, and spa services make it easily the most relaxing and secluded place near downtown Valparaiso. If a log cabin is what you're after, check out the Cabin on Swede Hill in nearby LaPorte.

Airbnb Cabin on Swede Hill Indiana Book Now

Closer to the Indiana Dunes, this one-bedroom condo on the marina is peaceful and romantic, with all you need to escape the city hustle.

Aibnb condo Indiana Book Now

Weekend Getaways for Couples From Chicago

If you have a bit more time for travel, put on a good playlist and juice up your carfor these weekend getaways for couples from Chicago. If you leave after morning coffee, you'll be settled in your getaway spot by lunch.

4. Door County, Wisconsin

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‌How to Get to Door County‌

Take I-94N to I-294N and head to I-43N. From there, take WI-54E/WI-57N to County Q to head into town. The trip takes about four and a half hours.

Cedarburg or Elkhart Lake are halfway points if you need to stop and stretch your legs in a quaint little town.

‌Things to Do in Door County‌

Door County's natural beauty is breathtaking, from the pristine waters of Cave Point County Park to the marvelous Niagara Escarpment. Trails, beaches, cliffs, waterfalls, and caves make Door County an ideal place to spend time together in the great outdoors kayaking, paddling, hiking, zip lining, or canoeing.

For those not-so-actively adventurous days, there are plenty of ways to snag some alone time and enjoy the stunning scenery from afar. Spend the day at Stone's Throw Winery, hop on the Door County trolley for a tour, or stay in a cozy Egg Harbor log cabin and venture into town for shopping, food, and drinks.

‌Where to Stay in Door County‌

Door County has no shortage of adorable cabins, charming bed-and-breakfasts, and boutique hotels. I recommend this Door County Honeymoon Barn Suite for its beautifully relaxing atmosphere, incredible lake views, and starlit nights.

Door County Honeymoon Barn Suite Book Now

The Chanticleer Guest House in Sturgeon Bay is one of my very favorite places to stay. The fully restored orchard farmhouse has lush bedding, beautiful gardens, and breakfast baskets, making it an ideal romantic retreat.

Chanticleer Guest House Chicago Book Now

5. Saugatuck, Michigan

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‌How to Get to Saugatuck‌

The drive from Chicago to Saugatuck is roughly 2 hours and 15 minutes via the Dan Ryan (I-94E). Take I-94E to the Indiana Toll Road and then to I-196N, following the signs to Holland/Grand Rapids. Head to the Blue Star Highway and drive into town via Lake Street.

Union Pier, Michigan is about the halfway point if you need a little breather.

‌Things to Do in Saugatuck‌

Saugatuck is called Lake Michigan's "Art Coast" for a reason. The galleries, artist studios, and overall colorful vibe of the town make for a very artsy getaway.

Picnic at calm, clear Oval Beach. We love to fill our picnic basket with local goodies from The Butler's Pantry, American Spoon, and The Wine Sellers of Saugatuck. Take a sunset cruise on the Star of Saugatuck or a tall ship sailing cruise on the Schooner Serenity.

Restore your mind-body connection through a couples massage at the Bella Vita Spa and walk through the Rose Garden, a little oasis at the corner of Mason and Butler in downtown Saugatuck.

Visit Virtue Cider for a cider house tour, enjoy a wine tasting at Fenn Valley Winery, or explore one of the Saugatuck Brewing Company breweries or tasting rooms.

‌Where to Stay in Saugatuck‌

The sweet Oriole cottage is a bright and cozy rental that feels secluded but is just a few blocks outside of town. It has a screened porch, a hot tub, and every comfort of home, including Wi-Fi.

Airbnb Oriole cottage Saugatuck Book Now

For its luxurious modernity, I also love The Hotel Saugatuck. Whether you stay in the boutique hotel or the cottage rooms, the guest rooms feature hydrotherapy tubs, fireplaces, and other high-end amenities that inspire romance.

The Hotel Saugatuck Book Now

6. Indianapolis, Indiana

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‌How to Get to Indianapolis‌

Chicago to Indianapolis is about three hours by car. Take I-90 E/I-94 E to I-65S toward Indianapolis. Take exit 113 toward Meridian Street straight into town.

‌Things to Do in Indianapolis‌

Indianapolis has at least six cultural districts, each with its own flavor. Explore them all on the Indianapolis Cultural Trail and the Monon Trail.

Mass Ave. is the artsy cultural district. Get a signature chocolate latte at Coat Check Coffee in the historic Athenaeum building. Broad Ripple, the oldest of the districts, hosts a year-round farmers market, and the up-and-coming East Market District is home to the Indianapolis City Market, a sprawling farmers' market and indoor shopping extravaganza. Love an old-school deli? Stop at Shapiro's.

Take a romantic, private gondola ride on the Indiana Central Canal, which runs right through downtown Indy. Stroll down the River Promenade to explore Indy's urban oasis, White River State Park. Put together a picnic and watch the sunset from Waterfront Pavilion.

Spend time surrounded by beauty at Newfield's, the art museum and 52-acre gardens about 10 minutes from downtown that also houses the original "LOVE" sculpture.

‌Where to Stay in Indianapolis‌

The swanky Bottleworks Hotel housed in the old Coca-Cola plant is modern, artsy, and lavish. It has it all, from a morning cup at Blue Collar Coffee Co. to a nightcap at Sundry & Vice cocktail lounge.

Bottleworks Hotel Indianapolis Book Now

This light-filled loft in downtown Indy is a cozy getaway in the heart of town. It's reasonably priced and has a private entrance and a hot tub.

Aibnb loft Indianapolis Book Now

Best Couples Getaways From Chicago

When you have a few days to spare for more than a quick day trip, hop on one of these short flights to romantic spots for couples getaways from Chicago that will make you feel like you're worlds away.

From South Carolina to Virginia, these hotspots aren't that far way by plane but still provide lots of exciting opportunities to explore.

7. Charleston, South Carolina

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‌How to Get to Charleston‌

Direct flights from O'Hare or Midway will get you to Charleston International Airport in under two and a half hours.

‌Things to Do in Charleston‌

Charleston's unique and historic charm makes it an ideal romantic destination, with cobblestone streets, colorfully dreamy architecture, and a gorgeous waterfront.

Grab a morning coffee (or mimosa) and stroll the waterfront to admire the stunning historic homes, from Waterfront Park to the battery. Enjoy an evening carriage ride downtown.

Take a culinary tour of the historic French Quarter and City Market, or plan a sunset dinner cruise on Charleston Harbor. If you're a history-loving couple, don't miss the Fort Sumter tours and cruises.

‌Where to Stay in Charleston‌

This secluded, bungalow-style guest house is tucked within walking distance of historic downtown Charleston. It's cozy, private, and has its own porch and a little garden.

Aibnb bungalow South Carolina Book Now

If you want something that is ultra-Charleston in looks and vibe, stay at the John Rutledge House Inn. The stately national historic landmark has upscale southern amenities like evening port, sherry, and brandy. The romantic getaway package is perfect for anniversaries or special dates and includes champagne, strawberries, dinner, and a rickshaw ride.

John Rutledge House Inn South Carolina Book Now

8. Alexandria, Virginia

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‌How to Get to Alexandria‌

A direct flight from O'Hare or Midway will land you in Alexandria in under two hours.

‌Things to Do in Alexandria‌

The ad slogan "Virginia is for lovers" refers to lovers of just about anything, because Virginia has it all: beaches, mountains, architecture, food, wine — you name it.

To immerse yourself in the history of this destination, stroll down Captain's Row, an 18th-century cobblestone block of Prince Street in Old Town Alexandria. Move over to King Street for an utterly charming collection of boutiques, restaurants, and bars. I highly recommend the bottomless brunch at Mia's Italian Kitchen.

Explore the Alexandria waterfront and Potomac River on a water taxi cruise or book a dinner cruise from nearby Washington, D.C. Stroll along the river in Rivergate City Park at sunset to catch views of Maryland and Washington, D.C.

‌Where to Stay in Alexandria‌

Enjoy your private garden with a fire pit, fresh local pastries, and crisp, comfy accommodations within two blocks of shops and restaurants in this luxurious apartment rental.

Aibnb Apartment Virgina Book Now

If you want to stay in the historic heart of Old Town Alexandria, the Lorien Hotel & Spa has dreamy guest rooms and a full-service spa. It's charming, refined, and oh-so-relaxing.

Lorien Hotel & Spa Virginia Book Now

9. Traverse City, Michigan

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‌How to Get to Traverse City‌

A nonstop flight from O'Hare or Midway to Traverse City's Cherry Capital Airport will land you at your destination in under an hour and a half.

‌Things to Do in Traverse City‌

Poised on the southern shore of Traverse Bay and insulated by the eastern shore of Lake Michigan, Traverse City has the topography, soil, and growing season that wine grapes adore. Choose a Traverse City Wine and Beer Tour to get a taste.

Explore downtown Traverse City's 150 shops, galleries, boutiques and eateries. Take a sunset stroll along Clinch Park's beach, which is crowded during the day, but offers lovely views of Grand Traverse Bay in the evening.

Take the 35-minute drive west to Sleeping Bear Dunes for a gorgeously picturesque beach. Hike the two-mile Empire Bluff Trail for breathtaking views of Lake Michigan. Or drive 35 minutes east and north to Torch Lake, a body of water so clear you'll swear you're in the Caribbean.

‌Where to Stay in Traverse City‌

Grant Traverse Resort and Spa is a beautiful place to disconnect and reconnect with luxurious rooms and every amenity, including a spa, casino, golf course, indoor pool, and fitness space.

Grant Traverse Resort and Spa Book Now

This loft space is a rental on the grounds of The Village, part of a historic preservation site. The renovated buildings were once the Traverse City State Hospital — a psychiatric institution. There is an Asylum Twilight Tour if you want a look inside the hospital's history.

Airbnb loft Traverse City Book Now

Romantic getaways from Chicago can also be found inside the Windy City. Wherever you choose to go, take your sense of adventure and romantic spirit with you. They'll never steer you wrong.