Bridge Insights

Staycations for Remote Workers this Holiday Season in the Midwest

Dec 1, 2023

Are you looking to get away without the hassle of taking a flight somewhere? Some of the best “getaways” are within driving distance of your local city! In the Midwest, there are many wonderful places to go to for a weekend getaway. Maybe you’re looking for something scenic, a wine trail, or maybe a grand spa and shopping excursion.

The holidays can be stressful, and we encourage everyone to take the time to unplug this season. Check out our top list of places below for an awesome staycation that will give you more time to rewind and less time traveling.

For the City Dweller

Where: Chicago’s Gold Coast, Chicago, IL

Are you looking for a weekend in the city, with plenty to do within walking distance? If so, plan your next trip at the Claridge House in Chicago’s Gold Coast neighborhood. One of the oldest neighborhoods in the city, this area of Chicago brings you back in time with architectural details and charming streets filled with beautiful homes that are always decorated with ample detail during the winter season. Everything you need is within walking distance, and Rush Street is a few blocks away giving a visitor several choices when it comes to dining and shopping. This neighborhood also is only a walk away from the Lincoln Park Zoo and the Lakeshore Path.

Stay at: Claridge House

Eat at: LUXBAR

Visit: Lincoln Park Zoo (Holiday ZooLights)

For the Wine Connoisseur

Where: Nashville, IN

When people think of wine trails, they most often think of places like Napa and Sonoma. All throughout the Midwest there are fantastic winery trails and winery towns that have given California wines a run for their money. Who doesn’t love a quaint town where the wine samples are free and you can walk to all of them in a downtown setting? If you’re looking for a charming getaway, where the wine is great, the food is comforting, and the town feels like a Hallmark Christmas movie, head to Nashville, IN. This town has many wineries within its downtown setting, and many more that line the outskirts! Ever heard of Oliver Wines? Their home base is right outside of Nashville, IN. This area is also known for its moonshine and scenic views. Nicknamed the “Little Smokies” because of the area’s resemblance to the Great Smoky Mountains, Brown County encompasses nearly 16,000 acres of rugged hills, ridges, and fog-shrouded ravines.

Stay at: Brown County Inn

Eat at: Hard Truth

Visit: Brown County Winery

For the Self Care Novice

Where: Lake Geneva, WI

Speaking of charming towns, Lake Geneva, WI makes our list of places to visit for a wonderful staycation. The beautiful lakefront, sprawling estates, and plenty of winter activities to do are only a few of the things that make Lake Geneva a place for people to return to season after season. If you’re looking for a relaxing weekend and an entire spa experience, we recommend heading to The Grand Geneva Resort and Spa. From massages and facials, and many more service offerings, you will leave your staycation from Grand Geneva feeling relaxed and recharged. Their downtown has plenty of cute cafes, shopping, and dining experiences. Outside of Lake Geneva are other quaint Wisconsin towns that are worth stopping through. One of our picks if you want a nice glass of wine would be Staller Estate Winery in Delavan, WI.

Stay at: The Grand Geneva

Eat at: Oakfire Pizza

Visit: Staller Estate Winery

For the Unplugged Adventurer

Where: Ottawa, IL

For those looking for a remote setting with access to plenty of nature, we recommend renting a tiny home in Ottawa, IL. While you’re on your remote getaway, you will be close to several state parks, including Starved Rock. This state park is known for its 18 canyons, which feature vertical walls of moss-covered St.Peter Sandstone formed by glacial meltwater that slice dramatically through tree-covered sandstone bluffs. The Lodge at Starved Rock also has wonderful wintertime activities including a 4-course dinner, trolley rides, cocktail pairings, and a winery. While there are plenty of hiking and winter activities that require no contact with other people, this area also provides those looking for a little bit of both that opportunity. In the area are also many restaurants, grocery stores, and highway access for peace of mind.

Stay at: Tiny Home in Ottawa, IL

Eat at: Thyme Craft Kitchen

Visit: Starved Rock State Park

For the Shopaholic

Where: New Buffalo, MI & Michigan City, IN

For those looking for a winter getaway and plenty of shopping, look no further than a trip to Michigan City, IN, and New Buffalo, MI. For those wondering, these two cities are only 15 minutes away from one another on the coast of Lake Michigan. A fantastic outdoor shopping center is located in Michigan City and accommodations are only minutes away in New Buffalo. The area also boasts many breweries and wineries, with many shops, casinos, and outdoor activities. Many resorts line the coast of these towns, but there are plenty of Airbnb and vacation rentals for the whole family to take a trip!

Stay at: The Harbor Grand Hotel

Eat at: Shoreline Brewery

Visit at: Michigan City Premium Outlets