Just before Cleveland, merge onto I-80 and follow this all the way across Ohio, Pennsylvania and New Jersey before crossing into Manhattan via George Washington Bridge. 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. The whole town gets decked out in style for the holidays. Located 90 . They don't run every day, but when they do they're really magical. First is the village of New Glarus. 10 hours 10 minutes from Chicago (660 miles). 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. Why you should visit: Orlando is known as a winter sun favorite so pack your sun cream and enjoy some time outdoors. Our travel tips: Winter weather in Savannah is changeable, but the year-round humidity can make even warm days feel chilly when you're outdoors for a while. Drive, reach and enjoy the beautiful states around. 12 hours 40 minutes from Chicago (800 miles). Note that to enjoy all the attractions Niagara Falls has to offer, you might need to factor in crossing the US/Canada border so make sure you have any paperwork you need (dependent on nationality). There are also several events to mark Dia de los Muertos in late October and early November. If you've had about enough of cheese, you can go on an ATV ride around the trail network around Monroe. The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. 4 hours 20 minutes from Chicago (290 miles). The Dells Boat Tours will take you through the narrow river passages - these Dells are gorges through layered rock formations that become small tall islands as the river widens. Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago. If you're not planning a trip until after Christmas, you'll be able to visit the Toronto Light Festival, when fabulous installations brighten up the city through the cold winter nights. It will satisfy a wide range of abilities, and you can also try out snow tubing and snowshoeing here. Road Trip From Chicago To Washington DC - LazyTrips If there's one reason to visit Milwaukee, it is to see for yourself what the beer capital of the United States really looks like! 2 hours 45 minutes from Chicago (186 miles). It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities. Time in the air: 3 hours. You can easily do a day trip from Chicago, but if you decide to come for the weekend, you can stay over at the Starved Rock State Park Lodge that comes complete with a pool and spa to unwind after your hiking. Fly from Chicago to Columbus, Ohio, for $167 round trip The most costly of our cheapest air fares from Chicago's O'Hare International Airport still comes in at an attractive $167 round trip, meaning it's now easier than ever for Illinois locals to make the quick 1.25-hour hop straight across the heartlands of the Midwest. Back in town you'll get beautiful winter views over icy Lake Michigan. Toledo is known as the Glass City, after the many glassmakers that set up here in the 19th century. 4 hours 30 minutes from Chicago (300 miles). Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia. This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place. Hot Springs (Arkansas) Distance: 650 miles. Nearby, Biltmore is a huge gilded-age mansion with vast formal gardens, trails to explore and its own winery. This award-winning, community-focused gallery always has something new to see, and with sculptures and exhibits inspired by nature, it makes the perfect complement to a day enjoying the views out on the mountain. Went to New York (which was fun) so that is covered. The area is also home to a number of very decent wineries. 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. 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. For the perfect post-ski wind down, visit the Spa at Boyne Mountain before you head home. Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. Our highlights: For many visitors, the main draw is the Olde World Christmas Market, a 10-day festive spectacular bringing together Czech, German and Russian Christmas traditions. The 2,470-mile road trip from Chicago to San Francisco takes 38 hours to drive. 15 Best Winter Road Trips from Chicago - LazyTrips 25 Best Road Trips From Chicago - LazyTrips Although there's the regular rush hour traffic that might slow you down a little, the city doesn't experience significant congestion. With many travelers heading to Asheville to see the stunning display of foliage in the fall, we'd recommend booking ahead to guarantee your choice of accommodation at this time of year. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own. Whether you're looking for an active break or a peaceful boat trip, there are plenty of opportunities to get out onto the water. MoneyGeek came up with this year's list by analyzing the FBI's crime statistics for 2021 (the most recent . If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. 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. Little Orleans Campground. 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. If you want to maximize your Swiss experience, then combine your road trip to New Glarus with a stop in Monroe - the Swiss Cheese Capital of the USA. If you'd like to take a little shopping excursion, Nashville (IN) has a great many galleries and artisan shops. Our highlights: The nation's capital is a fantastic place to visit during the holiday period. Places to visit about 500 miles from Chicago - Within Hours Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Whatever kind of winter road trip you're interested in, we've put together some of the key facts for a whole host of fabulous destinations. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh. The town of Holland sits along the length of Lake Macatawa that flows into Lake Michigan. Although a lot of people will travel to Wisconsin Dells for the waterparks, don't forget to go on a tour down the Wisconsin River gorge. With no cars on the island and a super relaxed vibe, you can take strolls, visit lighthouses and hike to see the Arch Rock on the east side of the island. Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. 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. Why you should visit: You can see the Nation's Christmas Tree, a century-old tradition in the city - it's illuminated from early December in a popular ceremony that for many marks the start of the holiday season. Louisville is best known as the host of the Kentucky Derby - the famous horse race takes place on the first Saturday in May and has run since 1875. Founded in 1778, Louisville is a really amazing mix of old and new. 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. If you want to strike out a little further and explore, you can go horseback riding or cross-country skiing through the woodlands or try out snow biking for something new. The rinks are super-festive in the run up to the holidays, and you can relax with a hot chocolate or a local craft beer afterwards. A few of the upcoming options on our road trip list are all due north in Wisconsin. 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. You will pass by some imposing homes and quiet lakeside neighborhoods with picturesque cafes. It was an early adopter of snowmaking technology in the 1950s. Plus, you can fill yourself with festive cheer with a visit to the traditional market at Love Park's Christmas Village, or a stroll through streets filled with fabulous Christmas lights. Rockford is the largest city in Illinois outside Chicagoland (the Chicago metropolitan area). 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. 1. Our highlights: The highlight of most people's visit to Niagara Falls is to see the mighty waterfalls up close, but if you visit in winter you can also marvel at the massive icicles that form right by the viewing platform on the Journey Behind the Falls. 'Peter Pan & Wendy' review: A real-live adventure this time from Disney 17 hours 30 minutes from Chicago (1,130 miles). Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. The village represents a historic view of Dutch settlements and you can even visit a wooden clog (shoe) making factory. Our travel tips: Although average temperatures sit around 60 degrees Fahrenheit in winter, they can drop much lower or rise as high as 80, so it's wise to pack for three seasons to be prepared for a winter trip here! As Christmas gifts go, a whole city is one we wouldn't mind receiving! 15 hours 10 minutes from Chicago (960 miles). 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. Best Weekend Getaways From Chicago: Road Trips & Itineraries - Thrillist As a result, you will find some great restaurants and interesting art galleries and independent craft shops up and down the coast - New Buffalo is great for its boutiques and farm shops. Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. Geneva, Illinois - 41.7 miles. Another is called the " Fire Sudatorium. These will carry you up to a quarter of a mile across the resort's valleys, giving you a bird's eye view of your stunning surroundings. If you're able to visit mid-week, you'll probably find the slopes are quieter. Also running from Thanksgiving right up to New Years Day is Celebration in the Oaks. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. The extensive and varied ski slopes here are great for a wide range of skiing abilities. 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. Alexander Molony as Peter Pan, Ever Anderson as Wendy, Joshua Pickering as John Darling and Jacobi Jupe as Michael Darling in "Peter Pan & Wendy," directed by David Lowery. You can easily visit for a day or stay the night to see more of the local sights and museums. You can get a tour of the mansion and explore the vast grounds which include 620 feet of shoreline. After taking I-90 E towards the edge of the city, turn onto I-65 and follow the interstate south, driving past Indianapolis and right the way across Indiana until you reach Louisville, Kentucky. You can also go on a tour of the Cedar Creek Winery and try the local wines which might just surprise you. Don't forget to check out some of the Smithsonian museums too they're free to enter so you can visit one or many, and enjoy some of the more popular sites without the crowds, especially if you're visiting after the holiday period. Getting to St Louis is easy - the I-55 will take you all the way to the Gateway City. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow. 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. At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. The long rows of vines stand out proudly in the snow and make a beautiful backdrop while you're learning about Icewine production or, more importantly, tasting a glass or two. Or if you're here a little earlier in winter, you can get yourself into the holiday spirit with a snowy visit to the Sculpture Gardens or enjoy some exhilarating winter sports.