You can easily fill a weekend here with fun and varied runs. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. Once you arrive at Mount Rushmore, you can also spend time exploring the stunning Black Hills and surrounding area. A few of the upcoming options on our road trip list are all due north in Wisconsin. A Little History. The World of Winter Festival is the perfect post-holiday pick-me-up - the ideal way to brighten up the dark, cold months after Christmas. Hot Springs (Arkansas) Distance: 650 miles. It is the only working Dutch windmill in the United States and it is beautiful in May when the weather gets good and the thousands of tulips flower. Morning departure is around 5% cheaper than an evening flight, on average*. If you are looking for cheap weekend getaways from Chicago, this is a good place to stay. 8 hours 40 minutes from Chicago (530 miles). 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. Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! After crossing the border into Canada, the road becomes ON-401. Any suggestions fellas? The village represents a historic view of Dutch settlements and you can even visit a wooden clog (shoe) making factory. 2 hours 50 minutes from Chicago (180 miles). This tradition has grown into thriving arts scene, making Toledo a great place to visit if you like exploring street art, outdoor sculpture or a trip to the theatre or concert hall. 506 miles east of Chicago: Upper - Kettle Creek State Park. Many visitors head to Denver en route to the Rockies, which are right on your doorstep if you're staying in the city. Parking can be difficult, especially in the summer months when hundreds of visitors head to town. The extensive and varied ski slopes here are great for a wide range of skiing abilities. Head up the CN Tower for great views of the city and Lake Ontario, which is particularly stunning when it starts to freeze over through the winter. Car production moved to other cities in the US, factories in Asia and Mexico and large blocks of Detroit became ghosts of their own past. Saugatuck, which sits at the center of the state's Art Coast, has been voted the Midwest's Best Beach Town, and its gently sloping sandy beach is the perfect place to spend an afternoon. Why you should visit: As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices. 506 miles southeast of Chicago: Toe River Campground. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience. For added romantic charm, put your skates on and have laps on one of the city's many ice rinks - there are over 50 to choose from. 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. A little further north from Chicago than Milwaukee is the town of Cedarburg. LazyTrips is a trading name of Uncle Bob Media Ltd. There's a real art to making Icewine and the conditions have to be just right to freeze the grapes for long enough on the vine. If you're able to visit mid-week, you'll probably find the slopes are quieter. 11 hours 50 minutes from Chicago (760 miles). The museum also contains an extensive selection of art by well-known artists and has a collection of Native American Art. The 830-mile road trip from Chicago to Washington DC will take you around 14 hours to drive non-stop. There are also several events to mark Dia de los Muertos in late October and early November. But did you know that every single participant has to wear one? Add in beautiful beaches all over, some big sand dunes, including the Indiana Dunes National Park and the pretty towns of Harbor Country. 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. As well as Mardi Gras, New Orleans is also a vibrant city where you can enjoy live music, fabulous food and warm winter weather - perhaps the closest you can get to a trip overseas without needing a passport! You can't take your car with you to Mackinac - you'll have to park it at one of the designated ferry parking lots and make your way across. 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. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition. It's not all about the outdoors though. While you're in town you can take a magical snowy hike through the trees at Madison Arboretum, then round off your day with outdoor dining - several Madison restaurants have heated outdoor domes so you can enjoy snowy views while dining al fresco. Stop at the Crane Orchards to sample one of their legendary pies as you make your way around! When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. High season is considered to be June and July. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh. There are a number of museums to explore - some of the main ones located along the Museum Row. PC . Though it was longer drive but not bad. 8 hours 20 minutes from Chicago (550 miles). Sundays have a free Jazz Brunch outdoor concert series along the scenic Riverwalk. Bonus: After Christmas, a free maze is built on the lake shore out of the branches of discarded Christmas trees, a custom that has become firmly cemented in Madison's holiday traditions now. Whether you want to enjoy the winter weather or escape from it, a winter road trip from Chicago can mean hitting the slopes at a ski resort, viewing iconic landmarks, taking a festive shopping trip or relaxing in the winter sun in the Southern states. After around 250 miles of driving you'll cross the Maumee River then turn off onto I-75 heading towards downtown Toledo. Outside of the downtown Fennville, you'll find rolling fields and orchards that are both pretty and make some great food. 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. Also running from Thanksgiving right up to New Years Day is Celebration in the Oaks. 4 hours 20 minutes from Chicago (300 miles). We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,. A wide selection of breweries includes European-style beers and the pizza-serving Harmony. Flight $$$: $500. Book a fantastic treatment or simply hang out in the sauna, steam room or heated outdoor pool to enjoy the mountain vibes from a different angle. You can get a tour of the mansion and explore the vast grounds which include 620 feet of shoreline. There are a number of different trails that will take you up and down the dunes, past groups of trees that have been overcome by the sand, dune blowouts and pine forests. You can easily visit Milwaukee for a day and see the beautiful architecture and the Harley-Davidson Museum where you can learn about the infamous motorcycle brand's history and have a go on a scarily realistic simulator. Join I-90 W and follow it for over 900 miles, all the way to South Dakota. Beer and baseball are the two things the city is particularly known for. Once you get to halfway point, you should spend a day or longer on Mackinac Island. to the Bacon and Brews event where you can sample fine bacon and beer pairings, there is always something happening. Traffic in Denver is heavy at rush hours as you might expect, but the Friday peak is a little earlier than other days so factor this in if you're trying to beat the crowds. If your time is limited, take your sled and enjoy a free downhill ride at one of the several hilly public parks in the city. Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Our highlights: You can see all the historic gems of Philly decked out with lights and trees for the holiday season, and the city's beautiful riverside setting just adds to the magic. Make sure you visit the Heidelberg project - the outdoor art installation uses salvage materials to highlight the plight of Detroit and its ongoing period of change through loud modern sculpture. Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. 13 hours 40 minutes from Chicago (925 miles). Alternative options are the Frederik Meijer Sculpture Park and the Fish Ladder Park. The town transported a 250-year old windmill from the Netherlands to Holland and placed it on its very own island that is now called the Windmill Island. As you'd expect, with much of the Midwest sitting under snow through the winter, the weekend trips you can take from Chicago all have a winter sports element to them. 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. This is a trip that will show off the best of what Lake Michigan has to offer - a complete circle of the lake, heading to Mackinac Island on the opposite corner before making the return trip. Absolutely. Whether you're looking for an active break or a peaceful boat trip, there are plenty of opportunities to get out onto the water. This means you probably won't see the grape harvest unless you're out in the vineyards at night - pickers tend to work by hand to make sure of the most perfect harvest possible. The route up to La Crosse will pass a few great stop off points - check out the steel Black Hawk Bridge over the Mississippi at Lansing and the Nelson Dewey State Park has some of the best panoramic views of the river and surrounding forests. You can also go on a tour of the Cedar Creek Winery and try the local wines which might just surprise you. As you make your way from Chicago to Philadelphia, make sure to fit in a visit to Bethlehem, PA, too. Our travel tips: Although temperatures are at or below freezing through most of the winter, you're not always guaranteed snow in Toronto, so be prepared that you might miss out on the insta-perfect images of this particular winter road trip. With art, culture, caf patios and waterfront dining, Toledo is a great short trip if you want a change of scene from Chicago. 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. It's a great way to experience this historic part of the city, full of character. Drive, reach and enjoy the beautiful states around. In Wasau, the nearest town to Granite Peak, there are some great food and drink options for the essential apres-ski part of the day! Continue along the interstate then, after skirting the west side of Lake Pontchartrain, merge onto I-10 which takes you into the center of New Orleans. Harbor Country is one of the most popular getaway destinations for Chicagoans. The 3 tallest sand dunes are all in the State Park with the tallest, Mount Tom, standing at 192 ft. The Blue Ridge Parkway starts in Asheville, and you can hop onto America's favorite drive to travel a section of this fabulous scenic route. Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races! 4 hours 20 minutes from Chicago (290 miles). Back in town, tour the River Arts District on foot to meet artists at work in their studios. Rockford lives up to its main nickname with plenty of outdoor spaces to explore - the Anderson Japanese Gardens, Klehm Botanic Garden and the Rock Cut State Park are all within the metropolitan area. The fast ferries will take under 20 minutes to get you there. If you're thinking of setting off on a road trip from Chicago in another season, check out our ultimate guide for Best Road Trips from Chicago for ideas and inspiration. Fennville has a few quirky local museums and things to see. It was an early adopter of snowmaking technology in the 1950s. Make sure you grab some food at the Root beer Stand. If you're wondering how the town got its name, it's as simple as it sounds it's because the lake is shaped like an Elk's heart. As well as being a relaxed and varied city, Asheville is the perfect gateway to the Blue Ridge Mountains, so a trip here offers a great combination of city vibes and the great outdoors. Of course, there are two sides to every story, and a few miles from Mount Rushmore you can visit the Crazy Horse Memorial.
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