The Best Winter Midwest Getaways from Chicago

October 20, 2023

Chicago winters are long and brutal. It’s this time of the year we need to get out. But when hopping on a plane from ORD to LAX isn’t in the cards, try these 6 places to escape the daily grind. All of these getaways are five hours or less.

Lake Geneva, Wisconsin

Located in the southeastern part of Wisconsin, Lake Geneva is a beautiful destination that is filled with fun and adventure. We always stay at the Grand Geneva Resort & Spa and take the kids to the Moose Mountain Falls Waterpark at Timber Ridge Lodge, which is a part of the Grand Geneva. It’s nice because once you are at the hotel, it has everything you need and you don’t need to leave. If you can sneak away for some adult time, I love their spa too. It’s located in a separate building tucked away.

If you’re looking for a more relaxed weekend, you can take a leisurely tour of the local wineries or book yourself a spa appointment. Afterward, take a walk around the charming downtown area of Lake Geneva and explore the historic architecture and shops. It’s probably one of my favorite, easiest getaways from the city.

Galena, Illinois

One of our favorite getaways is Galena! It’s an easy drive – just a little over 3 hours from Chicago with lots to do and see. We have stayed at an Airbnb or the townhomes at Eagle Ridge Resort, which is then a short drive to downtown. Indoor pool, spa, and beautiful grounds. They also have townhomes to rent on the property, great for families! See my babymoon blog post about Eagle Ridge here.

Grab a coffee and take the trolley (check their winter hours) on a scenic, historic tour of Galena where you’ll see many of the original early nineteenth-century buildings. You can take a hike with goats with Hoof It Goat Treks, and then shop the small boutiques & cafes that line the main streets. I love Bread and Vine or Otto’s (it’s rumored to be haunted!) for breakfast, brunch, or lunch, Isabella Ltd for gifts and home decor, Bloody Mary’s at Fried Green Tomatoes, and Poopsies for toys and gifts.

New Buffalo, Michigan

Many people think that New Buffalo is only a summer destination, but we actually love it during the winter because it’s empty! We love to go to David’s Deli for brunch, have Italian dinner at Brewster’s, and head to Sawyer for Sawyer’s Market which is next to Greenbush Brewing! For coffee, Whistle Stop is cute with great bagel sandwiches, and stopping by the Swedish bakery on Red Arrow Highway is a must! We also like taking a hike at Galien River County Park.

We usually get an Airbnb (here are two of the homes we have rented, home 1 and home 2– both highly recommended for families and both are walkable to town. We have also stayed at the Marina Grand Resort a few times and love it! It’s crazy expensive in the summer, but prices are much better in the winter. They have an indoor pool, a very small game, room, suites that come with kitchens, and an on-site restaurant! It’s right on the water. It’s beautiful!

Kenosha, Wisconsin

If you want to go skiing, we went to Wilmot Mountain which is about 50 miles outside Chicago. It’s an easy drive! You could easily do it in one day, but we decided to stay overnight in Kenosha, which is about 20 minutes from Wilmot.

We stayed at the Apis Hotel, a small boutique hotel and restaurant. It’s new and gorgeous! Walkable to downtown coffee shops like the Buzz Cafe and restaurants. Sazzy B is a good bar/restaurant! There’s a pretty path along the lake and a Kenosha public museum close by.

As for skiing, we loved Wilmot! Highly recommend a ski lesson if you’re a beginner like me.

Des Moines, Iowa

Des Moines, Iowa is such a cute little town. It’s family-friendly with also plenty to do if you want to make it a girl’s getaway or romantic weekend. Stroll the super cool Pappajohn Sculpture Park and then have dinner at the festive Exile Brewing (reservations recommended). The Science Center of Iowa is an interactive museum that is great for kids! Des Moines offers lots of holiday light shows, like the Jolly Holiday Lights at Adventureland Park and Gingerbread Lane, a neighborhood where 31 homes participate in telling an original Gingerbread story. Another favorite restaurant is Lachele’s Fine Foods!

Indianapolis, Indiana

Indianapolis, Indiana is about a 3-hour drive and it’s great for kids! The Children’s Museum of Indianapolis is phenomenal and can keep those kids busy all day. If the weather isn’t too frightful, visit 100 Acres: The Virginia B. Fairbanks Art and Nature Park for hiking, playing, and exploring. The Garden at Newfields has a Winterlight Show and for dining, I recommend: Almost Famous tapas bar, Festiva for Mexican cuisine, and Big Bear Biscuits for brunch!

Hopefully, some of these have inspired you to get outta town this winter season! If you need other winter or Chicago staycation things to do, check out my winter holiday hotel guide HERE.


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