How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain. Though it was longer drive but not bad. With art, culture, caf patios and waterfront dining, Toledo is a great short trip if you want a change of scene from Chicago. You might get spring, and then again, you might have winter still hanging on! Chicago is a fantastic hub for history, architecture, gastronomy and sports. Our travel tips: Visit the Luge in the evenings and you can warm up by a bonfire after your slide down the track. Our highlights: Toronto is a vibrant cultural melting pot, so when you spend time in the city you'll be able to enjoy influences on food, art and recreation from all over the world. You'll learn about the many faces of Lake Erie, from the Underground Railroad which ferried slaves to safety across the lake, to prohibition bootleggers. Snow in the city often isn't much fun, so head out to one of the mountains or lakes for a one-day road trip that lets you enjoy the winter weather at its best. Flight $$$: $500. Toledo is known as the Glass City, after the many glassmakers that set up here in the 19th century. A few of the upcoming options on our road trip list are all due north in Wisconsin. The laid-back, pretense-free. As far as Nashville I-55 runs parallel to the Mississippi before passing through Jackson. Why you should visit: With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip. Everything from cow's milk to goat and sheep milk is used and there are imitations of European cheeses and unique local flavors available. Things to do on Kauai include exploring the Waimea Canyon, Kkee State Park, Na Pali Coast and the Kalalau Trail. Whether you're looking for a festive shopping experience to ease you into the holiday mood, or a snowbird heading south for the winter, there are plenty of fabulous longer road trips that start out from Chicago. 15 hours 10 minutes from Chicago (960 miles). Sitting on Lake Michigan with the Great Lakes and a number of states within easy reach, there is every reason to get in the car and explore the surrounding areas of Chicago whether you are looking for a day trip, a weekend out or a longer adventure. Make sure you visit the Slugger Museum and Factory - this baseball bat manufacturer has tours where you can see the whole process and the side of the building has an exact scale replica of the Babe Ruth's Louisville Slugger bat, albeit a little larger at a length of 120 feet. The route then follows the river north - you can cross in and out of Iowa and then Minnesota from Illinois and Wisconsin as the river continues to be the state border along the length of this drive. Our highlights: The nation's capital is a fantastic place to visit during the holiday period. Outside of the theme parks, you can enjoy the Winter Park Christmas Parade, a long-standing Florida tradition, with dozens of troupes followed by Santa. To get to Louisville from Chicago, you will need to drive the length of Indiana until you reach the Ohio River - St Louis is right across the John F. Kennedy Memorial Bridge. You could come to Cedarburg on a long day drive, but it's really perfect as a weekend getaway destination. The city is in a prime spot with a lot of road trip options for you to escape to the surrounding destinations within 5 hrs drive. You can survey the options from atop the California Tower in Balboa Park. After a rapid period of growth through the first two thirds of the 20th century, Detroit suffered an economic collapse and a massive decline since the 70s. Why you should visit: From January to March the town hosts the World of Winter Festival, which sees dozens of huge ice sculptures on display and special events held across the town. You can also go on a tour of the Cedar Creek Winery and try the local wines which might just surprise you. You can easily visit for a day or stay the night to see more of the local sights and museums. Nicknamed the Forest City due to the area's verdant woods and rivers, Rockford is also known as the Screw Capital of the World. The Great River Road runs the length of the Mississippi river and you can drive part of it on a scenic road trip from Chicago. The city's popular Longwood Gardens is transformed with amazing lights and live music, so it makes a great place to spend some time after the sun goes down (which happens early in winter!). It's not all about the outdoors though. Featuring city breaks, small coastal harbor towns, outstanding natural parks and the occasional wineries and breweries, here are our 20 best road trips from Chicago ordered from closest to furthest away - make sure to read further down for more epic road trip itineraries! You will pass through the cities of Milwaukee, Green Bay, Traverse City and Grand Rapids which are all worth going to in their own right. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights. You can also find out more about the site at the Lincoln Borglum Visitor Center, or visit the Sculptor's Studio to find out more about how the monument was created. Nearby, Biltmore is a huge gilded-age mansion with vast formal gardens, trails to explore and its own winery. When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest! For something a little different, visit Wings Over the Rockies Air and Space Museum to see a large collection of planes, including many vintage models. People in the Dutch Village wear traditional clothing, play Dutch music and you can join in one of the mass dances if you'd like. If you're in Philadelphia towards the end of the holiday season, you'll be able to watch the Mummers' Parade on New Year's Day. The Windy City also boasts a stellar location, just a drive away from fascinating landmarks, charming small towns, scenic lakes and iconic cities if you'd like to venture out to explore. Our highlights: Just outside the city at Cascade Mountain and Devils Head Resort you'll find some exhilarating downhill skiing as well as snowtubing and sledding. The local Fermentorium brewery has some 24 different beers on tap - not too shabby for a local place! The must-see attraction on your trip to Mount Rushmore National Memorial is the famous cliffside sculptures of the presidents, which you can see up close if you follow the short Presidential Trail. From here, pick up I-76 and follow it straight down to Denver. Located right by Lake Ontario, you can enjoy frosty views out across the water, then head back into the city to indulge yourself in some culture or plain old festive cheer. You should ride to the top of it to get unbelievable views of the city below - tickets are $14 for adults and $11 for children with discounts outside weekends. Our highlights: The World of Winter Festival usually starts in the first week of January, and as well as ice sculptures you can see interactive installations from artists all over the world, with walking tours taking you through some of the outdoor art highlights. You could . From here, follow I-196 further around the lake shore. Further afield, the city is packed full of other shopping districts, including the West Village, Bleeker Street, Union Square and the Meatpacking District to name just a few. To help you make the most of this great drive, we've set out the best routes and places to stop . Less than half of Toronto's residents were born in Canada, making for a varied and welcoming city that's the perfect place to head to on a road trip. After heavy rainfall - this is also the perfect time for viewing colorful wildflowers. Rockford is the largest city in Illinois outside Chicagoland (the Chicago metropolitan area). Our travel tips: Some of the outdoor activities that Niagara Falls is famous for, notably the Maid of the Mist boat cruise, do not operate in winter, but as we've identified, there are plenty of other ways to enjoy views out across the falls. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. There are a lot of activities for children - special rides and a petting zoo so bring the family and enjoy a great weekend out of the city! The Cinco de Mayo festival is one of the biggest in the country, with parades, live music and dozens of food stalls to choose from. Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races! 2 hours 45 minutes from Chicago (186 miles). LazyTrips is a trading name of Uncle Bob Media Ltd. 11 hours 10 minutes from Chicago (700 miles). Wrap up warm and walk out towards Muskegon South Breakwater Lighthouse a really stunning sight or take a walk on the lake's frozen beaches. The dunes stretch along a 15-mile stretch of Lake Michigan and the National Park borders the State Park of the same name. Time in the air: 3 hours. Drive, reach and enjoy the beautiful states around. For the equestrian lover, Keeneland is a famous horse racing arena that attracts people from around the globe. Drive time: 2 hours from downtown. Although there's the regular rush hour traffic that might slow you down a little, the city doesn't experience significant congestion. You must try the Glarner Stube restaurant in town. The fastest way to get to Minneapolis from Chicago is to go the I-90 and I-94 route across Wisconsin. However, it's also famous for its harsh winters, so there might be times you want to head out of the city during the coldest months of the year. With large distances to cover, some of the early pioneers of flight lived and worked in this part of the country and you can also find out about the former Air Force base where the museum is located. The theme parks of Orlando are popular year-round, but during the winter you get to experience them all dressed up for the holiday season, and without the heat and humidity that can be a feature at other times of the year. To make the most of it, though, you really should consider stopping the night and exploring the local beer scene. There are festivals throughout the year from the world's largest Bratfest (you can eat a lot of sausages here!) Here are several interesting options that make a great family road trip and all within easy driving distance of Chicago. 1 hour 30 minutes from Chicago (93 miles). Make sure you grab some food at the Root beer Stand. This after-dark spectacle sees City Park lit up with more than a million lights. Parking can be difficult, especially in the summer months when hundreds of visitors head to town.