The 9 Best Weekend Getaways From Chicago

We love our fair city but sometimes all the noise, traffic, politics and people make us feel a little anxious, craving for a change of scenery just for a few days. Thankfully we’ve got plenty of options for weekend getaways that are just a short trip from Chicago.

We shared some of our favorites last year and added even more this time around. Whether you crave nature, a relaxing weekend of wining and dining or just a different skyline to enjoy, we share some of our favorite spots to check out the next time you feel a bit restless in the city.

Union Pier & Three Oaks Michigan
Sometimes you just need a breath of fresh air and a slightly slower pace compared to the daily hustle of life in Chicago. But if I’m heading outside the city for the weekend, I want to maximize my relaxing and minimize my travel time. Just less than 1.5 hours away right across the border of Michigan I’ve found the perfect spot to spend the weekend relaxing by a fire, soaking in a hot tub and enjoying a bottle of local wine. Union Pier is one of the many small communities right on the edge of the Michigan and Indiana border that are close enough to each other to drive and explore. I enjoy staying at the Sweethaven Resort in Union Pier. It’s right off the highway and a quick walk or bike ride down to the beach. It’s also just down the road from Round Barn Winery so stop in and grab a bottle of cherry wine on your way to your cabin. Sweethaven is ran by a lovely couple who make sure you have everything you need for your stay. Most of the cabins have private hot tubs which is the perfect place to relax and enjoy that cherry wine you picked up. Pick up a thin crust pizza from Mario’s and tuck in for a night by the fireplace with a good book.

After an evening of relaxing, spend the next day doing two of my favorite pastimes; drinking and eating. Round Barn has a great tasting room with a large selection of their wines, spirits and beer. And if you do a tasting they offer a discount on purchases. Next drive over to neighboring town Three Oaks and enjoy lunch at Pleasant House. These Bridgeport royal pies have many fans in Chicago and their second location also offers their own beer selections. My favorite meal to order is their chicken balti pie, flakey buttery crust packed with curry spices and chicken, some mash and buttered peas with mint. Afterwards head over to Journeyman Distillery just around the corner and grab a tour of the facility. At the end try some of the spirits they offer, grab a few bottles (my personal favorites are their Silver Cross whiskey and their Snaggle Tooth coffee liqueur) and then head to the bar for a seasonal cocktail or two. It’s nice to find a place so close to the city that still feels like a true getaway. — Lisa White

Union Pier And Three Oaks (Part of the Harbor County region) are located about 75 miles Southeast from Chicago off I-94.