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.

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.

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.

Wisconsin Dells, Wisconsin

f you are looking for a fun family trip, Wisconsin Dells is a family playground with SO many things to do. We had a great weekend vacation there last fall and we can’t wait to go back! We stayed at the Wilderness Resort which is America’s Largest Waterpark Resort! The Wilderness Territory has 4 indoor and 4 outdoor waterparks, over a dozen attractions, 3 mega arcades, an 18-hole championship golf course, spa, plenty of onsite dining, and hundreds of different lodging options from various styles of hotel rooms, villas, condominiums, and even luxurious five bedroom cabins! And yes, waterparks are included with your stay!

We stayed in a Wilderness on the Lake condo, which had a kitchen, washer/dryer, dining room, living room, multiple bedrooms, a sunroom, fireplace, and whirlpool! We had access to the main Wilderness Resort by a free shuttle that runs every 15 minutes or so. The condos and cabins would be great to share with another family or grandparents. There are tons of dining options at the resort and many restaurants deliver directly to the hotel. We tried Moosejaw and it was great!

Read more about our adventure here!

Mall of America, Minnesota

Although this might be a short flight away, I know many people who have driven it. We just did Mall of America in Minnesota and it’s like Vegas – but for kids. There is SO much to do. Not only is there the Nickelodeon Universe, there are lots of other attractions like Sea Life (the underwater 360 tunnel is really cool), Crayola experience (great for younger kids), Lego attraction, Flyover America, and more. There are hotels connected to the mall – JW Marriott and Radisson Blu. We stayed at the JW and it was great, plus they have an indoor pool. You can see my reel here of some of the things we did! 

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.

Christine