4 Days 240 Miles
4-Day Winter Road Trip: Outdoor & Urban Adventure from Chicago to Indiana Dunes National Park
Illinois, the Prairie State, is known for its gorgeous summers, but winter in this part of the U.S. stretches from November through April and is one of the most magical times of the year. Just because the temperature drops and the ground is covered with fluffy snow, it doesn’t mean that Illinois goes into hibernation. In fact, the crisp air and coating of white unlock a host of possibilities for fun and creating memories.
You can visit gigantic cities such as Chicago, or flat prairie lands, highlands, and rivers in the national parks. The state is also a haven for wildlife lovers, as you can spot many species roaming the snowy landscapes.
This four-day winter itinerary highlights some of the best things to do for an adventure-filled trip in a short space of time, including the canyons of Starved Rock State Park, the bright lights of Chicago, and the ruggedness of Indiana Dunes National Park.
O’Hare International Airport or Midway International Airport in Chicago offer the most flexibility and minimal travel time.
Where to Stay Near Starved Rock State Park
It is a good idea to stay at the Starved Rock Lodge to cut down on travel time, as it sits right at the top of the bluff. But the lodge also enhances the experience due to its history. You can opt to stay in one of the guest rooms or in the more contemporary hotel wing. The lodge has cozy lounges, a pool, and an authentic Midwest experience that you will struggle to find elsewhere. It even has a restaurant so you can enjoy a fantastic meal when you have finished exploring.
Day 1 – Starved Rock State Park
Starved Rock State Park is located 1.5 hours from O’Hare International Airport. It overlooks the Illinois River from its position high on the cliffs and is a favorite spot for day-trippers from Chicago.
The park was founded in the 1930s, attracting visitors who wanted to admire the area’s canyons and bluffs. As many of the rivers and streams are spring-fed, the canyons are home to majestic ice waterfalls in the winter.
Winter Hiking or Snowshoeing
Begin your first adventure at Starved Rock Lodge, our recommended lodging for the evening and the starting point of the canyons and a day of winter hiking.
Winter hiking is a little different from the summer. You will want to dress in layers and make sure to wear grippy waterproof boots. Alternatively, you can strap on some snowshoes to make getting to the frozen waterfalls much easier. Snowshoeing is easy and accessible to people of all fitness levels. It is the ideal way to see the delights of nature at a slower pace.
If you feel brave or energetic, you can go ice climbing on four of these frozen waterfalls. The smallest frozen waterfall, La Salle, is excellent for first-timers as it is only 20 feet high. More experienced ice climbers head to Wildcat, which is over 90 feet. If you are new to ice climbing, it is best to book a lesson. Ask at Starved Rock Lodge or the visitor center to find out about availability.
However, if you want to take it easy on your first day, jump in the car and head for the ice formations at the Ottawa and Kaskaskia Canyons. You can also start the Illinois Canyon Trail from the parking lot here, which provides spectacular views with a short hike.
But if winter hiking or ice climbing aren’t for you, you may want to head to the visitor center for a dog sledding demonstration. These usually take place in the morning, and there is a second one in the afternoon.
Day 2 – Chicago
Heading back to Chicago on day two of your trip gives you a very different backdrop for fun. The lower temperatures and snow give the windy city a magical ambiance and the opportunity for wintry adventures.
One of the must-do things in Chicago during the winter is ice skating at the Maggie Daley Skating Ribbon. The ribbon is located in downtown Chicago and is a unique experience. It’s a loop that takes you through a winter wonderland with urban scenery. Skating on the ribbon is free, but you can rent ice hockey and figure skates when you get there. You can even warm up with hot chocolate after your session.
Did you know Chicago is also an excellent venue for cross-country skiing? There are not many dedicated groomed cross-country skiing trails, so you have to do some homework to find them. But many of the nearby forests and state parks have terrain suitable for cross country skiing when the snow lands.
One of the best places for cross-country skiing in Chicago is the Arrowhead Golf Course in Wheaton. When the snow falls, the golf course is known as the Arrowhead Nordic Center and provides lessons and rental equipment. It is a great spot if you have never been cross-country skiing before, as the well-groomed trails are suitable for both classic and skate skiers. Once you get to grips with the basics, you can head to the neighboring Herrick Lake Forest Preserve for some lovely tree-lined trails.
You may be able to time your visit for the Polar Plunge in January. This annual event sees thousands of people taking a freezing cold dip in Lake Michigan. The event raises funds for Special Olympics athletes through fundraising and donation, but jumping in the cold water also has health benefits. It improves circulation, burns calories, and reduces stress. Those who brave the event are treated to food and drinks to warm them up when they emerge from the icy waters.
Where to Stay & Eat in Chicago
Staying along the lake in one of the city’s high rise hotels can be a luxurious treat. We recommend Fairmont Chicago, Millennium Park or W Chicago Lakeshore for their outstanding locations and amenities.
There are some excellent restaurants not far from The Level, including The Chicago Firehouse. This restaurant used to be home to Engine Company 104 of the Chicago Fire Department and is THE place to go for seafood and steaks.
Day 3 – Chicago
Chicago has far more to offer than wonderful outdoor activities in the winter, there are also world class museums, the extraordinary shopping along the Magnificent Mile, and of course the incredible views from atop some of the world’s tallest skyscrapers.
The Field Museum is one of the largest natural history museums in the world, its collections rival the Smithsonian and British Museum. A highlight of the museum is the Griffin Halls of Evolving Planet & SUE the T. Rex. This exhibition covers more than 27,000 square feet and includes more than a dozen dinosaurs, along with SUE the 40-foot-long Tyrannosaurus Rex. Beyond dinosaurs, the Field Museum has remarkable collections of American Indian artifacts, geological specimens, and dozens of new interactive exhibits and experiences that bring the wonders of the natural world to life.
Adjacent to the Field Museum is the Shedd Aquarium. The Shedd is closer to an indoor aquatic theme park than an aquarium, with indoor dolphin and sea lion shows, Beluga whales that live in their own 2 million gallon habitats, and penguins and alligators (not in the same habitat). The vastness of their exhibits and astounding array of aquatic life will transport you from the Arctic to the Caribbean, from the South Pacific to the shore of Lake Michigan.
Heading out from the museums, explore the Magnificent Mile, one of the city’s most famous areas for shopping and dining. There are more than 450 retailers along this stretch of Michigan Avenue, these range from small boutiques to grand department stores, to the shops of the most known luxury brands.
Finally, no trip to Chicago would be complete without heading to the top of a skyscraper. The Willis Tower, formerly the Sears Tower, was the world’s tallest building for nearly 30 years, and has one of the best observation decks in the city. On a clear day it is possible to see four states and more than 50 miles from the sky deck.
Day 4 – Indiana Dunes National Park
The final day of this Midwest adventure takes us to Indiana. Heading west of downtown Chicago, following Lake Michigan’s shoreline, you can get to Indiana Dunes National Park. The park runs for 15 miles along the banks of the lake and has lots to offer visitors.
The park’s 15,000 acres are perfect for spotting wildlife, hiking, cross-country skiing, and snowshoeing through the peaceful forests. You can rent your snowshoes and cross-country ski equipment for free at the Paul H. Douglas Center for Environmental Education for use on the Paul H. Douglas Trail. However, if you want to head to the Glenwood Dunes Trails or Tolleston Dunes Trail, you must bring your own equipment.
The Glenwood Dunes Trails is a large trail network with scenic loops through the rolling wooded dunes. There is a trail for everyone, as they range from less than a mile long to over 14 miles. The Tolleston Dunes Trail is just 2.9 miles and twists through the park’s oak savanna and wetlands. The trail is hilly in places, making it a good choice for advanced cross-country skiers.
Part of exploring the dunes is looking out over the frozen Lake Michigan. Here you will see that the ice turns the area into a winter wonderland. However, don’t get too close, as it is very dangerous. It may look strong, but it is, in fact, very brittle, so stay at a safe distance and certainly don’t step on it.
If you didn’t get around to ice skating in Chicago, you could have fun on the ice rink at the William E. Urschel Pavilion. It has a large arched roof and a state-of-the-art sound system to create a great atmosphere.
Where to Stay Near Indiana Dunes National Park
There are various accommodations to choose from near Indiana Dunes National Park. For example, you can stay in beachside vacation rentals, hotels, or even a vintage rail car turned into a B&B. Book a stay at Riley’s Railhouse in Chesterton for a one-of-a-kind experience to end your adventure.