You can also snowshoe, tube or skate if you want a break from the slopes. 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. 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. Whether you're looking for an active break or a peaceful boat trip, there are plenty of opportunities to get out onto the water. 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. As you make your way from Chicago to Philadelphia, make sure to fit in a visit to Bethlehem, PA, too. Around one-third of the city's population is Hispanic so as you might expect, there are some big festivals and celebrations that you don't see in other parts of the US. 11 hours 10 minutes from Chicago (700 miles). Located 90 . Head to Macy's, Bloomingdale's or Saks Fifth Avenue for wall-to-wall shopping opportunities, or take a walk along Fifth Avenue to indulge in designer brands. You must try the Glarner Stube restaurant in town. 15 hours 10 minutes from Chicago (960 miles). Then warm up in one of the city's fantastic museums, including the Royal Ontario Museum where you'll find a fascinating and diverse collection. 2643 Illinois Route 178. The same road takes you right across Indiana and Ohio then along the whole length of Lake Erie, before you finally turn onto NY-5 through Buffalo around 5 miles before you reach your destination. 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. Make sure you grab some food at the Root beer Stand. Still under construction, this monument is dedicated to the Lakota leader who fought against the federal government to try and protect Native American land from being seized. The small town of Oglesby, home to 3,600 people, is renowned for its natural beauty. Record-breaking April 13: Chicago snaps 136-year-old warm weather Expect fabulous parades, live music and all-night parties. Rib Mountain, part of the ski area here, is Wisconsin's tallest mountain so you'll find plenty of downhill runs here to suit all abilities. 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. Motor City is the second largest city in the Midwest after Chicago and is worth making the drive for. Morning departure is around 5% cheaper than an evening flight, on average*. So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers. The Indian Museum of North America is nearby too. 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. Minneapolis straddles both sides of the Mississippi and has over a dozen lakes within it's city limits which makes for amazing scenery. How to get there: Join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Another is called the " Fire Sudatorium. Get into the festive spirit and enjoy the iconic holiday views of the city - if it feels familiar, it's probably because they've featured in so many films and TV shows over the years. The classic town of Ann Arbor is a great stop on your way - this university town has classic architecture, art galleries and great small coffee shops for you to relax or grab some lunch. Make sure you check out a few live music venues. High season is considered to be June and July. Our travel tips: Book in advance if you're visiting Winterfest, as the town gets really busy. The 2,470-mile road trip from Chicago to San Francisco takes 38 hours to drive. 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. 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. 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. For a really exhilarating ride, fly right above the snow on one of the 9 ziplines. Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience and one that's different to any other trip you might take. The main attraction is a 21-mile loop around the lake with stunning forest scenery and great views of the water. Little Orleans Campground. 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. 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. Best Winter Road Trips to Take From Chicago - Thrillist The Warmest Place in Chicago. The hip city has a lot of things to see and experience. At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! It is a huge historic mansion built by Chicago beer tycoon Conrad Seipp in 1888. If that gets your creative juices flowing it's also possible to take a one-day art workshop or a longer summer school in the city. The cheese fondue is right up there on our list of the best foods in the world! Once you get to halfway point, you should spend a day or longer on Mackinac Island. Once you arrive at Mount Rushmore, you can also spend time exploring the stunning Black Hills and surrounding area. Treat your group to an exhilarating zip line adventure with Shawnee Bluffs Canopy Tour. Your email will not be provided to third parties. Fridays at the Hollywood Beach Theatre feature free live jazz, blues and pop music at oceanfront cafes. 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. 20 Best Weekend Getaways From Chicago - Time Out Chicago Rockford is the largest city in Illinois outside Chicagoland (the Chicago metropolitan area). 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. It eventually turns inland to take you right to Grand Rapids. Heading towards Lake Michigan, you will find the small harbor village of Saugatuck. Road Trip from Chicago to San Francisco - LazyTrips If you're here to relax, escape the hustle and bustle with a stroll around Toledo Botanical Gardens or head out to Wildwood Preserve Metropark to follow its many trails on foot or 2 wheels. Roadtrips to do in 3 days from Chicago 8-9 hours driving max 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. 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. You can explore the spectacular underground rock formations on a guided tour, then spend some time looking for wildlife at the grass prairie which forms the overground part of the national park. For those who want to go on a longer road, trip, the options above may not quite cut it so here are some longer routes that you might like the sound of: By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. 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. 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. One of the great things about Toledo is that although it's one of the largest cities in Ohio, visiting is relatively straightforward. The festival also hosts many fun events. 2 hours 40 minutes from Chicago (145 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. Other activities include spending the day at Kalapaki or Po'ipu beaches, setting. Although this is a long drive, it's a really straightforward one. The dunes stretch along a 15-mile stretch of Lake Michigan and the National Park borders the State Park of the same name. Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. For a more magical festive feel, head to Frederick Meijer Sculpture Gardens. 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! 2 hours 50 minutes from Chicago (150 miles). Drive, reach and enjoy the beautiful states around. 24 Top Weekend Getaways From Chicago - US News & World Report Everything here is about cheese. Road Trip From Chicago To Washington DC - LazyTrips The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience. Weather at the end of March can be iffy. One that stands out for its festive themes is the Grinch-mas Who-liday Special at Universal Islands of Adventure. Mount Rushmore is set on the edge of the Black Hills, so if you're spending longer in the area you can head out into the great outdoors to hike, bike and enjoy the scenic drive along the Needles Highway. From here, follow I-196 further around the lake shore. 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. Alternative options are the Frederik Meijer Sculpture Park and the Fish Ladder Park. 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. 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. 605 S. Prospect St., Galena IL, 800-717-2317. Then head quickly back into the warmth of your hotel to warm up. 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! The Warmest Place in Chicago This Winter - L Stop Tours Of course, NYC is famous for its shops, so leave some space in your case for whatever gifts and treats you might pick up while you're in town. Visit the theme parks in their holiday finest whether your first choice is Walt Disney World, Universal Orlando, SeaWorld or Legoland Florida, each one will be suitably festive with parades and events to match. Or if you're feeling more active, there are sledding slopes in the park too. If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. Wisconsin Dells is known for two things - its scenic Wisconsin River gorge and the high number of waterparks which has given the town its nickname as the Waterpark Capital of the World. Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago. Cities 9 hours from Chicago 9 hours: Ely, MN 8 hr 56 min: State College, PA 8 hr 55 min: Huntsville, AL 8 hr 51 min: Pigeon Forge, TN 8 hr 46 min: Lutsen, MN 8 hr 46 min: Fergus Falls, MN 8 hr 41 min: Joplin, MO 8 hr 35 min: Niagara Falls, NY 8 hr 32 min: Topeka, KS 8 hr 31 min: Grand Rapids, MN 8 hr 27 min: Tunica, MS 8 hr 24 min: Hibbing, MN Best attractions: The Museum of the Rockies, which has the largest collection of dinosaur bones in the U.S. Also, just a 90-minute drive . After crossing the border into Canada, the road becomes ON-401. After heavy rainfall - this is also the perfect time for viewing colorful wildflowers. 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. Where's the warmest, sunniest place in Chicago during the winter months? Here are several interesting options that make a great family road trip and all within easy driving distance of Chicago. 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. 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. You might get spring, and then again, you might have winter still hanging on! You can also tour a museum ship to get a feel for the history of the lakes. How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville. 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!). Once Christmas and New Year are behind you, the party season in New Orleans really gets going. You can even ride across the river on the Chain Ferry, one of the last remaining in America. Lake Monroe is the state's largest man-made lake. The same road takes you right into Philadelphia. 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. If you're feeling active, there are places where you can sled on the frozen sand dunes. 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. Founded in 1778, Louisville is a really amazing mix of old and new. Hot Springs (Arkansas) Distance: 650 miles. Many visitors head to Denver en route to the Rockies, which are right on your doorstep if you're staying in the city. 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. It runs parallel to Lake Erie, so if you have a little longer to make your trip then you might like to pause along the way to admire views across the lake. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. 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. Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races! Time in the air: 3 hours. The local Fermentorium brewery has some 24 different beers on tap - not too shabby for a local place! Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia. Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota. You'll finally turn off the interstate at Rapid City, joining US-16 for the last few miles of your drive to Mount Rushmore. (866) 399-3866. www.grizzlyjacksresort.com. You can join the river at Savanna or a little further down at Clinton depending on the route you take. How to get there: This is a really simple trip just follow I-90 all the way from Chicago. 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. A particular highlight in Muskegon is its Luge track, which is open to the public. There's another dozen smaller lakes dotted around which breaks up the city into smaller neighborhoods and adds a lot of character. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades. 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. 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. 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. 1 hour 20 minutes from Chicago (80 miles). Chicago is a fantastic hub for history, architecture, gastronomy and sports. You'll have seen pictures of the beautiful and elaborate masks that are such a feature of the Mardi Gras parades. For the equestrian lover, Keeneland is a famous horse racing arena that attracts people from around the globe. Here you can join in with the 9-day Winter Festival (late January). The locals didn't stop at naming the lake after the slightly better known one in Switzerland. Overnight on the California Zephyr gets you to Denver where the weather is just as cold as Chicago but you'd be in a cosmopolitan city. 1 hour 30 minutes from Chicago (100 miles). Instead, workers used dynamite to shape most of the sculpture. Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. Driving time from Chicago: One and a half hours Our neighbors to the north will make you feel right at home with a seemingly endless supply of craft beer and cheese. Back in town, tour the River Arts District on foot to meet artists at work in their studios. 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 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. But that's just the welcome mat to this SoCal haven. You could . 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. The Garfield Park Conservatory, of course. Our travel tips: You don't have to have your own equipment to enjoy skating, snowshoeing or skiing it's available to rent at many of the attractions. If you want to test your senses, the Limburger cheese holds the title of the world's worst smelling cheese and is only made in Monroe. 'Peter Pan & Wendy' review: A real-live adventure this time from Disney Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions. 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: Granite Mountain is one of the oldest ski resorts in the United States, and it's been at the forefront of innovation in the skiing industry. Back on dry land, if you're still feeling energetic you can explore the trails of Saugatuck Dunes State Park, or follow the 300 steps to the top of Mount Baldhead to take in the lake view. 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. Our highlights: There are so many memorable festive moments to fit into a winter trip to New York City, it's hard to know where to begin. 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. Get a full list of up to 500 cities nearby Chicago. Why you should visit: The shortest trip on the list, Lake Geneva makes a great weekend getaway due to the short driving time, plus the area is perfectly set up for visitors to enjoy the winter weather. This idyllic shoreline in Michigan's southwestern corner stretches from the Indiana border to the town of Sawyer. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh. Then join I-196 and follow it north along the lake shore until you reach Holland.
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