10 Romantic Getaways Near Chicago, Illinois

Posted by
Brittany Varano
November 08, 2022
Updated March 28, 2023

The River Birch Cabin. Photo: Airbnb

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Romance undoubtedly fills the Chicago air, but sometimes a romantic getaway from the bustle of city life helps reignite love’s spark.

Home to an iconic skyline of glass skyscrapers along the Chicago River, the Windy City is a destination that needs no introduction. As the country’s third largest city, Chicago offers many romantic things to do for couples, like going for a walk on the beaches of Lake Michigan, catching a Broadway show in the Theater District, or sipping cocktails high above at the CloudBar.

But as thrilling as Chicago’s best attractions are, it’s only natural to want to spice things up. Around the city and off into neighboring states, couples can spend quality time together while escaping the chaos of the concrete jungle. Whether a visit to the countryside or a glamorous hotel on the lake, these romantic getaways near Chicago will add a little zing to your love life.

Related Read: 8 Cozy Cabins Near Chicago Offering an Escape to Nature

1. Deer Path Inn

Deer Path Inn
Photo: Deer Path Inn

Why you should stay: A sophisticated four-star hotel along Chicago’s North Shore.

  • Location: Lake Forest, Illinois
  • Sleeps: 2-4
  • Minimum stay: 1 night
  • Rates from: $349/night

Housed in a half-timber Tudor mansion, Deer Path Inn offers a European escape without traveling far outside the city. Home to English hospitality and an assortment of unique experiences, guests can enjoy traditional afternoon tea, grab a cold beer at the authentic pub, or relax in the English garden.

Tastefully decorated rooms are on offer at the inn, and upgrade options include spacious suites, some of which feature a wet bar or fireplace. The hotel is also equipped with a fitness studio and a highly regarded restaurant, The English Room, serving international cuisine and, surprisingly, a large sushi menu for carry-out.

This romantic getaway isn’t far from Forest Park Beach and the best restaurants in Lake Forest (one of Chicago’s ritziest northern suburbs), so you can easily craft an entire romantic weekend. The hotel is also near the Lake Forest metro stop, only about an hour’s train ride from Union Station.

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Follow ‘em: @DeerPathInn

2. The Buffalo House

buffalo house getaway
Photo: Airbnb

Why you should stay: A quaint countryside home within walking distance to the idyllic shores of Lake Michigan.

  • Location: Michiana, Michigan
  • Sleeps: 8
  • Minimum stay: 2 nights
  • Rates from: $225/night

Trade the concrete streets and steel skyscrapers of Chicago for a stay at The Buffalo House. This log home is the definition of cabin chic and features beautiful touches like a buffalo bust, a stone fireplace, and exposed wooden rafters. In the kitchen, a Smeg fridge and retro oven will inspire you to whip up home-cooked meals during your visit.

The wooded property is peaceful and serene, made even more enchanting by the outdoor fire pit and screened-in porch that’s complete with lounge chairs and a couch. There is also a public beach just a five-minute walk down the road, perfect for turning your trip into a beachy getaway.

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Follow ‘em: @BuffaloHouseMichigan

3. Modern Cabin in the Woods

modern romantic cabin near chicago
Photo: VRBO

Why you should stay: A spacious and private cabin with an outdoor hot tub.

  • Location: Saugatuck, Michigan
  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $500/night

Active couples seeking a romantic getaway have plenty to keep them busy at this modern cabin in the woods. The house features an open floor plan where floor-to-ceiling windows illuminate the tasteful and contemporary decor. The primary bedroom’s ensuite bathroom features a luxurious soaking tub and walk-in shower. There’s also a game room where couples can enjoy billiards and ping pong.

For those looking to venture out, Saugatuck is a beloved destination known for its Lake Michigan beaches, artistic flair, and LGTBQ+-friendly attitude. Not to mention, the cabin is near local wineries and cideries, the shores of Lake Michigan, and trails through the Allegan State Forest.

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Related Read: 9 Fabulously Unique Places to Stay in Illinois

4. Serenity Springs

serenity springs cabins
Photo: Serenity Springs

Why you should stay: Well-appointed private cabins at a couple’s resort about an hour from downtown Chicago.

  • Location: La Porte, Indiana
  • Sleeps: 2
  • Minimum stay: 1 night
  • Rates from: $259/night

Outdoorsy couples will appreciate the romantic reprieve in nature offered at Serenity Springs. This cabin resort was designed with couples in mind, reflected in the romantic amenities provided in the cabins. Each cottage is outfitted with heated floors, a fireplace, and a jacuzzi tub, and guests can choose between a lake, pond, or channel view.

While booking, you can purchase add-on romance packages that include rose petals, wine, and candle-lit dinners, perfect for celebrating a special event. The 85 wooded acres help create distance between the cabins and provide a place to wander during your stay, plus the sweeping dunes and natural beauty of Indiana Dunes National Park are less than 20 minutes away.

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Follow ‘em: @SerenitySpringsGetaway

5. Dunefarmhouse

Photo: Airbnb

Why you should stay: A modern home in the Tyron Farm green community near Lake Michigan beaches.

  • Location: Michigan City, Indiana
  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $254/night

The Dunefarmhouse is an architecturally stunning home that’ll wow you the moment you pull into the driveaway. Inside, the open floor plan, fireplace, and colorful furniture create a welcoming environment. This home is so unique that travel publications like TimeOut have dubbed it one of the top getaways in the Midwest.

More than 200 acres of woodlands surround this contemporary home, where guests can take a stroll along a well-marked 5k trail or drive a few minutes to the nearby Indiana Dunes. This romantic getaway is just over an hour by car from Chicago but is also accessible via Amtrak and the South Shore Line.

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Follow ‘em: @Dunefarmhouse

6. The Nest

romantic cottage near chicago
Photo: VRBO

Why you should stay: An airy beach home with unobstructed lake views and high-end touches.

  • Location: Union Pier, Michigan
  • Sleeps: 4
  • Minimum stay: 3-4nights
  • Rates from: $450/night

The Nest is a small slice of paradise overlooking a quiet stretch of Town Line Beach. This one-bedroom boasts a cozy sunroom, perfect for soaking up majestic views of Lake Michigan. The magic continues throughout the home, especially in the bedroom.  Furnished with intimate touches like a fireplace and an ensuite bathroom with a jacuzzi tub, this property is sure to turn up the romance.

Relax outside on the wooden deck complete with a grill (and fantastic lake views), perfect for an afternoon cookout, and guests can take a dip in the hot tub around the back. There’s also tons of romantic activities nearby, like visiting St. Julian Winery or playing a round of golf at the Woodlands Course at Whittaker.

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Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

7. Hüüsli

romantic getaway in the dunes
Photo: Airbnb

Why you should stay: A stylish log cabin with an expansive outdoor area complete with a deck and firepit.

  • Location: Michiana, Michigan
  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $249/night

At Hüüsli, guests are treated to a recently updated home brimming with Swiss-inspired design. Eye-catching elements like white shiplap walls, vaulted ceilings, and a stone fireplace create an environment that’s both cozy and airy. In the kitchen, the hosts have set up a coffee counter stocked with a Keurig machine and all the fixings needed to make a perfect cup of coffee.

Other thoughtful details include a fondue kit for DIY date nights, high-speed WiFi, and convenient keyless entry. Whether you spend time relaxing in the sunny four-season room or curled up on the couch in the lofted nook upstairs, Hüüslii provides a relaxing getaway just over an hour from Chicago. Not to mention, Michiana’s quiet beach is an easy five-minute walk from the house.

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Follow ‘em: @Huusli_Cabin

8. Victoria Resort Bed & Breakfast and Cottages

Victoria Resort Bed & Breakfast and Cottages
Photo: Victoria Resort Bed & Breakfast and Cottages

Why you should stay: An all-inclusive bed and breakfast along the lake with an onsite pool and tennis courts.

  • Location: South Haven, Michigan
  • Sleeps: 2-6
  • Minimum stay: 1 night
  • Rates from: $139/night

Nestled along Lake Michigan, the Victoria Resort B&B is an excellent place to enjoy some rest and relaxation with a loved one. The resort offers spacious cottage rentals and homey hotel rooms for any occasion. Each room in the B&B comes furnished with romantic touches like a whirlpool tub and fireplace, as well as modern conveniences that include a coffee maker and mini fridge.

The cottages can accommodate four to six people and feature a living space, private kitchen, porches, and outdoor grills. Wake up each morning to a fresh breakfast spread complete with coffee, juices, fresh fruit, and more.

Located in South Haven, just about two hours away from Chicago, there’s tons to do around Victoria Resort, from hiking and biking to checking out the beaches, learning about the area’s maritime history, and exploring the quaint downtown filled with local shops, cafes, and galleries.

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Follow ‘em: @VictoriaResortBnB

9. LePin Cottage

le pin cottage
Photo: VRBO

Why you should stay: A 1920s cottage that oozes romance not far from Michigan’s Warren Dunes State Park.

  • Location: Sawyer, Michigan
  • Sleeps: 3
  • Minimum stay: 2 nights
  • Rates from: $200/night

Featured in Better Homes and Garden, the LePin Cottage is a quaint one-bedroom cabin with a screened-in porch. This historic home was once used to house local vineyard workers but has since been transformed into a peaceful vacation rental for two. Homey and luxurious touches fill the cottage, including a wood-burning fireplace and a bubbling hot tub. Better yet, pets are more than welcome, so you won’t need to worry about kenneling.

One guest review on Vrbo sums up the property perfectly, saying, “We loved our stay at Eileen’s cozy, well-appointed cabin! It was the perfect home base for beach trips, wine tasting, and antiquing. We also loved the hot tub and fire pit! The cabin is close to everything while also feeling very private—we even saw deer in the backyard on our first evening!”

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Related Read: 10 Best Illinois Glamping Rentals

10. The River Birch Cabin

The River Birch Cabin
Photo: Airbnb

Why you should stay: A mid-century modern A-frame cabin within walking distance of Lake Como.

  • Location: Lake Geneva, Wisconsin
  • Sleeps: 5
  • Minimum stay: 2-3 nights
  • Rates from: $238/night

The River Birch Cabin is a pet-friendly getaway that’s as welcoming as it is beautiful. The home’s sloping roof, wooden surfaces, and expansive windows are an interior design dream. Upstairs are two additional twin beds for larger groups, quartered off by a wall of colorful stained glass.

From the primary bedroom, sliding glass doors open to a spacious balcony overlooking the wooded backyard. In the evening, sit next to a blazing fire with your partner roasting marshmallows beneath the stars. Or, if it’s too chilly, warm up inside next to the stunning malm fireplace that anchors the main living area.

Lake Geneva isn’t far from the cabin and has long been a vacation getaway for Chicagoans, thanks to its historic downtown, massive lake, numerous trails, and history as a spa destination.

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Follow ‘em: @RiverBirchCbin_CabinFever

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