BEST Winter Getaways Near Chicago (2024 Guide)

The best winter weekend getaways near Chicago in 2024. From romantic getaways for couples to fun winter road trips for families and friends, there is something for everyone on this list.

Winter Getaways Near Chicago/ Road Trips from Chicago in Winter

Looking for the best winter getaways from Chicago? If you can’t fly somewhere warm and escape winter in Chicago, embrace the cold and snow and visit these incredible winter getaways near Chicago.

(And make sure to check out my essential road trip packing list (with free printable pdf) to make sure you have all your road trip essentials before you go!)

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. 

Lake Geneva, Wisconsin

Visiting ice castles in Lake Geneva Wisconsin is one of the best things to do in the winter

Lake Geneva is a great winter getaway near Chicago. Located only about 90 minutes from downtown Chicago, it is close enough to visit on a long day trip from Chicago.

Visitors can go skiing, snowboarding and sledding at the The Mountain Top at Grand Geneva Resort. Wilmot Mountain, another skiing resort near Lake Geneva, also offers tubing.

Other winter outdoor activities in the area include snowshoeing, cross-country skiing as well as ice skating.

Lake Geneva Wisconsin ice castles at night

One of the best things to see in Lake Geneva in the winter is Winter Realms (formerly the ice castles), a unique frozen attraction. The man made ice castles are worth seeing both in the day and at night when they are lit by colored LED lights. Dates are announced about a week before their opening but the ice castles are usually open from mid-January to end of February. Read more about visiting the ice castles here.

A popular winter event in Lake Geneva is Winterfest (January 31 – February 4, 2024), a nine-day annual festival dedicated to art, winter, and fun. One of the highlights of Winterfest is watching teams of snow sculptors and artists compete in the U.S. National Snow Sculpting Championship.

Find more things to do in Lake Geneva in the winter here.

Stay: Grand Geneva Resort & Spa

Getting There: By Car: Lake Geneva is approximately 83 miles from Chicago

Elkhart Lake, Wisconsin

While Elkhart Lake is a great summer lake getaway, it is also worth visiting in the winter. Dog sledding, snowshoeing, skiing and carriage rides are some fun winter activities available in the area. Visitors can also explore The Ice Age Trail.

Schnee Days Winter Festival (January 26 – 28, 2024) is a weekend of winter fun and a celebration of snow, with various activities includding the SchneeLauf 5K run/walk, annual chili cook-off, and children’s games.

Find more things to do in Elkhart Lake in the winter here.

Stay: The Osthoff Resort

Getting There: By Car: Elkhart Lake is 150 miles from Chicago (about 2.5 hour drive)

Cheap Car Rentals

Galena, Illinois

Galena is great winter weekend getaway whether on a romantic trip or traveling with kids. Galena is a charming and historic small town. A large portion of the city is listed on the National Register of Historic Places and there are many historical sights to explore including the Ulysses S. Grant Home, the Elihu B. Washburne House, Dowling House and the Old Market House. Visitors will also enjoy strolling on half-mile historic Main St. loaded with one-of-a-kind shops and restaurants.

In addition to exploring the historic town, visitors can go skiing or snowboarding at Chestnut Mountain Resort, which has 19 total ski runs and a 7-acre terrain park suitable for a variety of experience levels.

The Nordic Center at Eagle Ridge Resort offers many fun outdoor winter activities including outdoor ice skating on their 1.5-mile long pond, cross country skiing, snowshoeing trails, sledding and even skijoring (a cross between cross-country skiing and dog-sledding).

Visitors can also go hiking or snowshoeing through Casper Bluff Preserve, the Buehler Preserve and the Galena River Trail.

Winter events include: Chocolate Lovers Stroll (February 10, 2024), Big Nut & Little Nut Big Air Competition (March 2, 2024), and the Galena Whiskey Weekend Grand Tasting (March 9, 2024).

Winter Carnival at Eagle Ridge Resort & Spa is a popular annual outdoor winter celebration during President’s Day weekend (February 16-19, 2024) featuring all types of winter activities including Fire and Ice winter shows, ice turkey bowling, s’mores making, ice carving stations and an ice bar featuring marshmallow shots.

Find more things to do in Galena in the winter here.

Stay: Country Inn & Suites by Radisson

Getting There: By Car: 164 miles driving distance from Chicago

Dubuque, Iowa

Dubuque, Iowa’s oldest town, is located across the Mississippi River about 20 minutes from Galena, Illinois. With its historic architecture and hilly landscape, Dubuque becomes magical when covered with snow.

Go skiing and snowboarding at Sundown Mountain Resort, with 21 ski runs and two terrain parks. Go hiking, cross country skiing or snowshoeing on the trails at Mines of Spain or Swiss Valley Nature Preserve.

Every year, Dubuque celebrates the Winter Arts Snow Sculpting Festival (the State of Iowa’s Official Snow Sculpting Competition) in its downtown Washington Park. Typically held the 2nd full weekend in February, teams of professional, amateur, and collegiate artists transform snow into masterful works of art. (The winning team is offered the opportunity to represent the state of Iowa at the U.S. National Snow Sculpting Competition in Lake Geneva, WI the following year.)

Find more things to do in Dubuque in the winter here.

Stay: Hotel Julien Dubuque

Getting There: By Car: Dubuque is 178 miles from Chicago (just over a 3 hour drive)

Frankenmuth, Michigan

Frankenmuth is known for being Michigan’s Little Bavaria. It is also home to Bronner’s Christmas Wonderland, the world’s largest Christmas store, which is open year-round.

Frankenmuth is a Christmas getaway from Chicago with many things to do during the holiday season.

Other things to do in Frankenmuth during the winter include ice skating, cross country skiing at Heritage Park and sledding at Memorial Park. Visitors than want to escape the cold can visit Frankenmuth Brewery and two of Michigan’s top indoor waterparks.

Don’t miss the annual Zehnder’s Snowfest (January 24-28, 2024), that includes one of the top snow and ice sculpting events, a fireworks display, petting zoo and children’s activities.

Stay: Bavarian Inn Lodge

Getting There: By Car: 298 miles (about a 4.5 hour drive) from Chicago

What are your favorite winter weekend getaway from Chicago?


Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.