Find a Romantic Illinois Getaway

December 03, 2018

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Illinois is home to millions of love stories. All over the state, you can escape the everyday with your special someone and enjoy the magic and beauty Illinois has to offer.

Chicago and Beyond

Oak Park

The tree-lined streets of suburban Oak Park are made for wandering and dreaming—maybe even dreaming of which house you’d most want to live in.

The homes here are simply beautiful. The Frank Lloyd Wright designs are the highlights—you’ll find more here than anywhere else in the world. But wander any streets of Oak Park’s historic districts and you’ll find plenty to think about for the next phase of your relationship…

When you’re done wandering, grab dinner around Lake Street and watch a movie at historic Lake Theatre. Be sure to try the pie from Spilt Milk for a slice of heaven.

Stay: Harvey House Bed & Breakfast

Harvey House BedroomHarvey House is not only a beautiful place to stay (and top-rated B&B on TripAdvisor), they specialize in romantic getaways. Get the Romance Package and you’ll arrive to find a bottle of chilled champagne and a box of locally made chocolates waiting for you in your room.


Woodstock is well-known as the filming location for the 1993 Bill Murray comedy Groundhog Day, but it’s also a delightful town perfect for a couple of days away (rather than the same day over and over again).

Take a walk around Historic Woodstock Square and the surrounding streets. It’s a wonderful mix of artisan retailers, restaurants and bars. During the summer months, it’s home to a farmers’ market on Tuesday and Saturday mornings. During the holiday season, it lights up for the enchanting Festival of Lights.

For the full Woodstock experience, catch a show at the Woodstock Opera House. It’s a spectacular building, home to concerts, musicals, plays, dance and more.

Stay: The Cherry Tree Inn Bed & Breakfast

cherry tree innIt was love at first sight for the owners—love of the inn, that is. They stayed at this Victorian-style mansion as guests, then decided they’d buy the place. You can’t get much better endorsement than that.

Great Rivers Country


If Hollywood needed to build a set for “charming small-town America,” it’d probably look a lot like Galena’s historic Main Street. The meandering rows of red brick buildings house more than 125 independent stores, eateries, boutiques and galleries you won’t find anywhere else. The perfect chance to surprise each other with one-of-a-kind gifts.

Once you’ve seen it up close, see it from the air. A hot air balloon ride at sunset is a moment you’ll never forget.

Stay: Goldmoor Inn

Goldmoor Inn Spring AerialsGoldmoor Inn sits on a bluff overlooking the Mississippi River, giving you a gorgeous, relaxing view of the water below. The suites offer whirlpool tubs, cozy fireplaces and hand-carved furniture. Or for a little more privacy and simple charm, choose your own cottage or cozy log cabin.


Elsah has been voted the most scenic spot in Illinois. A lot of contenders could have claimed that title—but you’ll see why people picked this small, secluded village between Grafton and Alton, right near the Mississippi River.

There’s beautiful scenery and a laidback atmosphere, but Elsah is perhaps most notable for what it doesn’t have: the hustle and bustle of 21st century life. Indeed, Elsah is often referred to as “the town that time forgot,” so if you’re looking for some quality time for just the two of you, make Elsah your getaway.

Stay: The Green Tree Inn Bed & Breakfast

Green Tree Inn, ElsahA quaint and peaceful village calls for quaint and peaceful lodging. The Green Tree Inn has well-appointed rooms, amenities aplenty and some of the friendliest innkeepers you’re likely to find anywhere. There’s even a pet-friendly room, should you want to stay close to your fur-baby.

Land of Lincoln


Here’s another town that’s like a step back in time. Almost as old as Illinois itself, Jacksonville is full of history, and full of impressive historic sites to explore.

But there’s plenty from the 21st century to enjoy, too. Try a couples’ massage and facial at Inner Harmony Day Spa. Admire the art at the David Strawn Art Gallery, housed in a former mansion. 

Stay: Blessings on State Bed & Breakfast

Blessings On StateYou’ll remember a stay at this award-winning bed and breakfast. Blessings on State is the realization of innkeeper Gwenn Eyer’s life-long dream, and the comfort and experience reflect that. Blessings on State offers more than one romantic package, so you know they specialize in giving couples that something special.

Trails to Adventure

Shawnee National Forest

Shawnee was made for couples who enjoy the great outdoors. It’s home to some of Illinois’ best natural sights – Giant City State Park, Lake of Egypt, Cave-in-Rock State Park and Garden of the Gods among them. All of them are fantastic for hiking, sightseeing and, of course, taking some amazing couple photos. (Proposal photos, too!)

Stay: Timber Ridge Outpost & Cabins

Timber Ridge InnTimber Ridge is home to an incredibly cool accommodation option: a treehouse! Sit outside under the trees and listen as the birds serenade you. Only risk is, you’ll feel so relaxed and at-one with nature you won’t want to get out and explore the wider area… but then again, on a romantic weekend, maybe that’s not a problem.

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