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. 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. 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. 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. Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia. 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. I-80 is a notoriously busy road, with heavy commercial traffic and few landmarks of interest. If you're here in winter, check out the National Gingerbread House Competition visitors can view entries into this big-money event. Flight $$$: $500. How to get there: Follow I-90 out of the city then pick up I-94 and head east towards Detroit. The Swiss Historical Village is a great live museum which has kept 14 buildings in the style of the original 19th century settlement. 2 hours 30 minutes from Chicago (155 miles). 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. You can also enjoy a number of holiday markets, to really get you into the festive spirit. 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. Best Spring Break Road Trips from Chicago - Windings to Unwind Most people come to Saugatuck to spend time by the water, enjoying the sunshine and refreshing lake water by day then watching the sun go down with a local craft beer. The two-lane road winds its way through the mountains, with plentiful overlooks and hiking trails to stop and explore. Our travel tips: Visit the Luge in the evenings and you can warm up by a bonfire after your slide down the track. Denver is the gateway to Rocky Mountain National Park, as well as being a great place to head to in winter if you want to ski or snowboard on nearby slopes. 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. Why you should visit: The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. There's another dozen smaller lakes dotted around which breaks up the city into smaller neighborhoods and adds a lot of character. 'Peter Pan & Wendy' review: A real-live adventure this time from Disney " There's also an "Amethyst Room," whirlpools infused with jasmine and weirdly good organic fried chicken. Our highlights: The nation's capital is a fantastic place to visit during the holiday period. The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. Mount Rushmore is a unique national monument that's a must-see for many Americans and tourists alike, which makes it the perfect destination from Chicago. 489 miles northeast of Chicago: Lake Bernard Park. Then join I-196 and follow it north along the lake shore until you reach Holland. 20 Best Weekend Getaways From Chicago - Time Out Chicago Why you should visit: Wisconsin's state capital has all the cultural and foodie delights that you'd expect in a big city, with added snow that opens up a whole range of other activities to enjoy. Our travel tips: Pack layers, as even Florida can experience cooler days, but rest assured that with heated pools and plenty of daytime sunshine, you can enjoy yourself outdoors right through the winter. Join I-90 E to head out of Chicago then merge onto I-94 to continue to follow the shore of Lake Michigan. Once a month the district comes to life with live music and guided tours, plus the chance to taste local wine. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February. Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota. Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. The detour will add around two and a half hours so bake that into your planning and consider stops along the way. The 3 tallest sand dunes are all in the State Park with the tallest, Mount Tom, standing at 192 ft. This idyllic shoreline in Michigan's southwestern corner stretches from the Indiana border to the town of Sawyer. Olympian Mark Grimmette trained on the Luge track here when he was young and went on to compete at five Winter Olympic Games, winning medals at two of them. You must try the Glarner Stube restaurant in town. It's the perfect place for a romantic getaway - wrap up warm and enjoy snowy views over the beautiful city and lake before warming up with a hot chocolate and a loop or two around an outdoor ice rink. The hip city has a lot of things to see and experience. The city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment. At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. How to get there: Head east out of Chicago on I-90, keeping Lake Michigan on your left, then continue on I-94 as far as Lake Joseph. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter. There are also several events to mark Dia de los Muertos in late October and early November. The 10 Cheapest Flights from Chicago | Hopper It is more than 10-14 hours to get to a warm beach from Chicago. 5 Winter Road Trip Ideas to Warmer Destinations - Auto Lab Geneva, Illinois - 41.7 miles. Oglesby and its neighbor Utica lie nestled into a curve of the Vermilion River and is perfect for exploring some of the best outdoors in Illinois. The festival also hosts many fun events. The famous architect built the house in 1951 and it is interesting to see how far ahead of its time it is in terms of its design and accessibility - the look is incredibly modern despite some 70 years passing! 5 hours 40 minutes from Chicago (350 miles). 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. How to get there: Follow I-90 east across Indiana. Although there's the regular rush hour traffic that might slow you down a little, the city doesn't experience significant congestion. Nearby, Biltmore is a huge gilded-age mansion with vast formal gardens, trails to explore and its own winery. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience. Weekend Getaways from Chicago: Market Street Inn - 3 hours . Asheville is packed full of history, but the modern city has a distinctly creative vibe that makes it really unique. Or if you're feeling more active, there are sledding slopes in the park too. There's a real variety of activities to enjoy here take to the snow for an active day outside, then relax at a beautiful spa. Towns like New Buffalo, St. Joseph, Benton Harbor, Holland, Saugatuck and Grand Haven provide pristine beaches, great shopping, lakeside restaurants and front-row view of sunsets over Lake Michigan. All through the winter, you can also enjoy the shops and restaurants on fabulous River Street, the perfect place to spend some time whether you're looking for gifts to take home or just something special for yourself. You might get spring, and then again, you might have winter still hanging on! 4 hours 30 minutes from Chicago (300 miles). 4 hours 20 minutes from Chicago (290 miles). With a lot of water activities on the lake, the parking lots can fill up quickly so make sure you get here in the morning to get a spot. 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. It will satisfy a wide range of abilities, and you can also try out snow tubing and snowshoeing here. There are festivals throughout the year from the world's largest Bratfest (you can eat a lot of sausages here!) How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts. Your email will not be provided to third parties. 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. Motor City is the second largest city in the Midwest after Chicago and is worth making the drive for. 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. Remember that Minneapolis can get cold, and even feel cool in the summer. And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet Florida sun including hourly snow flurries. 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! 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! Once Christmas and New Year are behind you, the party season in New Orleans really gets going. The Garfield Park Conservatory, of course. Today the city is undergoing a massive regeneration effort - downtown Detroit is becoming more hip and vibrant and one by one, the delapidated old factory buildings are being converted or replaced by new structures. Winters are bitterly cold and very snowy - that drive from Chicago might not be the best idea in the middle of February! 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. I don't want to go to the Wisconsin Dells like every year but something different, fun, good places to visit, similar to New York. 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 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. Why you should visit: As you'd expect in a town that sees significant snowfall from December to February, you can enjoy a range of winter sports. Winter Weekend Getaways Near Chicago - Chicago Parent After passing New Baltimore and Everett, change onto I-70 and continue on through the Appalachians before joining I-270 at Frederick and following it right into the center of Washington DC. These Are the 5 Warmest Places in Chicago Right Now - PureWow The best thing about Madison, like many places in Wisconsin, is the food. 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. Skate beneath the massive Christmas tree at the famous Rockefeller Ice Rink, before heading up to the Top of the Rock to take in the view of New York in the snow. Many visitors head to Denver en route to the Rockies, which are right on your doorstep if you're staying in the city. Plus the views from the vineyard are sublime! Some travellers prefer to make this journey on a longer route via the I-90, heading south near Mount Rushmore to reach Denver. Why you should visit: Orlando is known as a winter sun favorite so pack your sun cream and enjoy some time outdoors. Then head quickly back into the warmth of your hotel to warm up. There are a number of museums to explore - some of the main ones located along the Museum Row. 6 Best Road Trips From Chicago | Travel + Leisure Best road trips from Chicago Shutterstock 1. Bonus: If you're here before the holidays, get into the festive spirit at the Distillery District Christmas Market, which runs from mid-November until New Year. This leads you eventually onto I-95, which you'll follow south to Savannah. Hot Springs (Arkansas) Distance: 650 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). How to get there: Similar to the Grand Rapids trip, follow I-90 then I-94 east out of Chicago as far as St Joseph. 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. You could come to Cedarburg on a long day drive, but it's really perfect as a weekend getaway destination. Minneapolis straddles both sides of the Mississippi and has over a dozen lakes within it's city limits which makes for amazing scenery. 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. Best Warm Weather Destinations For Winter - CBS Chicago If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. Boyne Mountain Resort Distance: 5-hour drive Michigan winters are best captured with the ski resort of Boyne. With its artisan produce, a relaxed country vibe and outdoor activities on and off the lake, Harbor Country is a perfect antidote to the hustle and bustle of the city. 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. Our travel tips: The town will be extremely busy while the Christmas market is running, so book accommodation and any special activities well in advance. Getting to St Louis is easy - the I-55 will take you all the way to the Gateway City. Another is called the " Fire Sudatorium. Fun/Scenic Places within 10 hours hour or less roadtrip from Chicago - Yelp 12 Best Road Trips From Chicago - TripHobo The cheese fondue is right up there on our list of the best foods in the world! Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races! You could probably make the return trip in a day, but the journey can take up to 3 hours one way from Chicago so make it into a weekend and add a few stops at Fennville and the Harbor Country (see both above) on your way. From Louisville, I-64 takes you east to Lexington, then turn onto I-75 to make your way through Tennessee to Knoxville. Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. The parade brings together dragons and lions dancing through DC's streets, as well as drummers, dance troupes and firecrackers - it's a real feast for the senses. Add in beautiful beaches all over, some big sand dunes, including the Indiana Dunes National Park and the pretty towns of Harbor Country. 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. Savannah is a great place to visit all year round but come in winter to enjoy this fabulous city without the summer crowds or humidity. Home to the huge Miller Brewing Company, Milwaukee is better known for having a huge selection of seriously good micro-breweries and small beer manufacturers. Drive, reach and enjoy the beautiful states around. The whole town gets decked out in style for the holidays. At Denver Art Museum you can see another collection dedicated to the heritage of this part of the country, as the Petrie Institute for Western American Art is housed here. So, sit back, relax, and learn all you need to know in planning a road . This Mom n pop classic fast food diner has been in Oglesby since 1955 and serves top notch root beer floats and burgers. One of the best places to visit in Illinois, this state park features 18 canyons and 13 miles of hiking trails to explore. Greater . One is the Forever Curious Children's Museum - a non-profit organization created to spark a love for learning in kids of all ages. If you're crossing over the Canadian border to visit Niagara-on-the-Lake, the Icewine vineyards and wineries are probably the first thing that will get your attention. 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! 24 Top Weekend Getaways From Chicago - US News & World Report Though it was longer drive but not bad. You will be forgiven for thinking you were teleported to central Europe the moment you get to New Glarus. 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. If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well. 8. Rising 462 feet above the sea, the carillon tower recently reopened to the public after 80 years in solitude. Roadtrips to do in 3 days from Chicago 8-9 hours driving max It was founded by a group of Swiss settlers from the Swiss canton of Glarus in 1845. At night, you can see the falls lit up in spectacular illuminations as part of the Winter Festival of Lights. 11 hours 10 minutes from Chicago (700 miles). Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. 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. Absolutely. Spring Break Family Destinations Near Chicago - Chicago Parent Alternative options are the Frederik Meijer Sculpture Park and the Fish Ladder Park. Follow the Great River Road as it twists and turns and you will be rewarded with great views the entire way. Everything here looks, feels, smells and tastes Swiss. 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! Bozeman, MT. The Indian Museum of North America is nearby too. To make the most of it, though, you really should consider stopping the night and exploring the local beer scene. 11 hours 50 minutes from Chicago (760 miles). 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. If you're having issues using the site, please enable JavaScript and refresh your browser. You should definitely visit New York in winter so you can say you've experienced them all first-hand. No, it's not a typo - this is the third destination on our list of road trips from Chicago that is exactly 300 miles away! As you make your way from Chicago to Philadelphia, make sure to fit in a visit to Bethlehem, PA, too. 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. RV campgrounds 500 miles from Chicago. When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. Of course, there are two sides to every story, and a few miles from Mount Rushmore you can visit the Crazy Horse Memorial. Galleries, restaurants and local businesses come together to bring some warmth and cheer to the new year, with a legendary chilli cook-off, Soup-A-Thon and ice sculptures dotted around town. 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. If St Louis Cardinals are playing, it's worth going if you can get your hands on some (expensive) tickets - they are one of the most successful baseball teams of all time and baseball is the number one sport in town. So, pack up your skis and look out for your skates - but don't worry if you're not the biggest fan of the slopes, since you'll also find great restaurants, beautiful views and stunning spas at these weekend destinations. 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. Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. The event runs in late Jan or early Feb, and hundreds of the city's restaurants showcase their best meals at reasonable prices - the perfect way to brighten up a long, cold winter. You can also snowshoe, tube or skate if you want a break from the slopes. This waterfront city is the only destination on this list that takes you to another of the Great Lakes. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here. Otherwise you can find a selection of different cheese styles and types. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow. (Getty Images) Known as . The track is open to kids as young as 8 so bring the whole family and see if any of them catch the sliding bug.