Keep reading to find out where you could go, how to get there, and our pick of what's waiting for you when you arrive. How to get there: Join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Once you get to halfway point, you should spend a day or longer on Mackinac Island. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter. Here you will find a great white sand beach and stroll along the boardwalk, watch local boats go by or explore the shops along the docks. Denver also has a host of fabulous cultural attractions, so don't overlook the city itself on your way up to the mountains. But that's just the welcome mat to this SoCal haven. You can easily fill a weekend here with fun and varied runs. If you're here in winter, check out the National Gingerbread House Competition visitors can view entries into this big-money event. Remember that Minneapolis can get cold, and even feel cool in the summer. 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. ETA: 10+ hours with couple of short breaks. 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. You must try the Glarner Stube restaurant in town. Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. 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. It's not all about the outdoors though. St Louis, MO Driving time from Chicago: 4 hrs 30 min While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly. A quick road trip from Chicago to Milwaukee will take you north along the I-94 to the point where three separate rivers (Milwaukee, Menomonee and the Kinnickinnic) merge and flow into Lake Michigan. 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. Fridays at the Hollywood Beach Theatre feature free live jazz, blues and pop music at oceanfront cafes. The same road takes you right into Philadelphia. This idyllic shoreline in Michigan's southwestern corner stretches from the Indiana border to the town of Sawyer. After crossing the border into Canada, the road becomes ON-401. And one of the three sections of the Hoosier National Forest is immediate to this area. How to get there: This is a really simple trip just follow I-90 all the way from Chicago. Alternatively, tour the galleries and independent shops in the city's downtown area, which showcase the work of the thriving local arts community. You can also go on a tour of the Cedar Creek Winery and try the local wines which might just surprise you. One of the great things about Toledo is that although it's one of the largest cities in Ohio, visiting is relatively straightforward. It eventually turns inland to take you right to Grand Rapids. Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. 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. 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. Alternative options are the Frederik Meijer Sculpture Park and the Fish Ladder Park. Greater . Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own. You might consider day trips from Chicago to Milwaukee on the train. Back in town, the Ice Castles at Geneva National Resort & Club are a must-see. Cool down in warmer weather by riding the natural waterslide at Sliding Rock. There are also several events to mark Dia de los Muertos in late October and early November. 3 hours 20 minutes from Chicago (190 miles). 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. PC . It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities. Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest! Outside of the downtown Fennville, you'll find rolling fields and orchards that are both pretty and make some great food. You also don't have to book attractions weeks in advance, and you can find reasonably priced accommodation in the downtown area. 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. Bonus: These days you usually need to take a ferry across from Manhattan to Staten Island, but back in 1780 the entire harbour froze so hard that it was possible to walk all the way across the river. Where to Stay. Everything here is about cheese. So, sit back, relax, and learn all you need to know in planning a road . 1. Drive, reach and enjoy the beautiful states around. The 830-mile road trip from Chicago to Washington DC will take you around 14 hours to drive non-stop. Why you should visit: Orlando is known as a winter sun favorite so pack your sun cream and enjoy some time outdoors. Named after the tall cedar trees, it is particularly well known for its lush forests that cover the hills around Cedarburg. Located 90 . 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. Treat your group to an exhilarating zip line adventure with Shawnee Bluffs Canopy Tour. 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! The extensive and varied ski slopes here are great for a wide range of skiing abilities. 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. As well as all the holiday attractions and the chance to see some of the world-famous monuments beautifully surrounded by snow, the crowds at the city's museums are likely to be quieter during the winter. Any suggestions fellas? Weekend Getaways from Chicago: Market Street Inn - 3 hours . San Diego San Diego boasts 260 sunny days a year, miles of rugged beachside and barking seals. 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. 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. 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. Although this is a long drive, it's a really straightforward one. 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. Best road trips from Chicago Shutterstock 1. The whole town gets decked out in style for the holidays. If you're visiting at other times during the winter, there's still plenty to do in Elkhart Lake. The city was offered up to President Lincoln as a Christmas Gift during the Civil War. 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. 1. As well as being able to see the famous memorial in person, this is a great road trip that takes you from one side of the Great Plains to the other via some interesting and varied cities. 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. 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. While both parks are not as large as some, there is plenty to explore with trails going through canyons and some amazing rock formations. 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. The main attraction is a 21-mile loop around the lake with stunning forest scenery and great views of the water. You could . You might not have thought of Minneapolis as a city break destination from Chicago, but Minnesota's largest city is an amazing mix of culture, music, awesome food and the outdoors which you really have to visit. The detour will add around two and a half hours so bake that into your planning and consider stops along the way. 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. Rising 462 feet above the sea, the carillon tower recently reopened to the public after 80 years in solitude. You could come to Cedarburg on a long day drive, but it's really perfect as a weekend getaway destination. 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. 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. The Garfield Park Conservatory, of course. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts. 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. 4 hours 30 minutes from Chicago (300 miles). Key stops include Minneapolis, Sacramento, Albuquerque, Las Vegas and Monterey, plus the Grand Canyon, Mojave National Preserve, Lake Tahoe and Yellowstone National Park. If you're travelling at this time of the year you can also stop off at New Hope, PA, as you make your way from Chicago to New York City. For summer fun during the winter months, Grizzly Jack's Grand Bear Resort is the place to be. After around 250 miles of driving you'll cross the Maumee River then turn off onto I-75 heading towards downtown Toledo. You will pass by some imposing homes and quiet lakeside neighborhoods with picturesque cafes. Once you arrive at Mount Rushmore, you can also spend time exploring the stunning Black Hills and surrounding area. The main attraction is the carved cliff face featuring four Presidents of the United States. 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. 6 hours 30 minutes from Chicago (430 miles). But did you know that every single participant has to wear one? 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. 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! It's a tiny city with less than 1000 residents but its white-boarded houses, scenic sand dunes and fabulous beach make it a popular place to come to escape the city. Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check . Join I-90 W and follow it for over 900 miles, all the way to South Dakota. 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. 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. 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!). 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. If you've had about enough of cheese, you can go on an ATV ride around the trail network around Monroe. There are only 3 other Luge tracks in the whole of the United States, so if you've always fancied trying out this exhilarating sport, this is probably your best chance. From mid-January you can see parades and events starting up, then the main event, Mardi Gras, starts on Shrove Tuesday and carries on for two weeks. The 3 tallest sand dunes are all in the State Park with the tallest, Mount Tom, standing at 192 ft. You might get spring, and then again, you might have winter still hanging on! 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. Millions of years of geologic changes are reflected at the Garden of the Gods in 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. 1 hour 30 minutes from Chicago (100 miles). Otherwise you can find a selection of different cheese styles and types. With heavy snowfall possible, parts of the Blue Ridge Parkway and other smaller roads are likely to be closed at times in the winter, so check ahead if you're hoping to travel a particular route. The town on its western end is called Lake Geneva, the lake just to the north is called Lake Como with the town of Como sitting along it. As far as Nashville I-55 runs parallel to the Mississippi before passing through Jackson. PLAN YOUR TRIP: Visit Fodor's St. Maarten Guide Jo Ann. There are festivals throughout the year from the world's largest Bratfest (you can eat a lot of sausages here!) Why you should visit: New York City puts on an amazing display for the holidays from festive lights to Christmas trees and fabulous window displays throughout the city, all with a thick covering of snow. 17 hours 30 minutes from Chicago (1,130 miles). 2 hours 40 minutes from Chicago (150 miles) 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. When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. 15 hours 10 minutes from Chicago (960 miles). Flight $$$: $500. Absolutely. A particular highlight in Muskegon is its Luge track, which is open to the public. Combined with St Paul, the two merged metro areas are known as the Twin Cities and are one of the largest in the Midwest. Along the way you'll pass the cities of Madison, La Crosse and Sioux City, and you'll cross both the Mississippi and Missouri Rivers. For a different experience of New York in winter, skip the crowds and visit in January to enjoy NYC Winter Jazz Fest or NYC Restaurant Week, where restaurants put on their best fare at affordable prices. The main attractions are the two major parks - the Starved Rock State Park and the Matthiessen State Park. Our highlights: There might not be snow and ice on the ground, but Savannah manages to fill the holiday season with its very own brand of festive charm. Just after St Joseph, turn off onto I-196 where the interstate divides, and carry on north along the shore until you reach Saugatuck. Ride down the Kalamazoo River on a paddle steamer, explore the lakeshore and river in a kayak, or charter a yacht. 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. This can be particularly handy if you're staying a little way out of town, or if you want to avoid a long walk back to your parking spot at the end of the day. 8 hours 20 minutes from Chicago (550 miles). Though it was longer drive but not bad. If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. Then join I-196 and follow it north along the lake shore until you reach Holland. Once a month the district comes to life with live music and guided tours, plus the chance to taste local wine. You won't need any previous experience or equipment, as your entrance to the track includes a lesson and all the equipment you'll need to enjoy your visit safely. From here, turn onto Route 31 which takes you on to Muskegon. On the south side of the lake is the Black Point Estate. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. How to get there: Follow I-90 out of Chicago then merge onto US-41 at the southern tip of Lake Michigan and continue south past Terre Haute and Vincennes. A work on this scale had never been attempted in the country before and Gutzon Borglum, who led the project, quickly identified that chisels would hardly make a dent on the vast rockface. This makes for one of the best road trips from Chicago. 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. Asheville is packed full of history, but the modern city has a distinctly creative vibe that makes it really unique. 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. Toledo is known as the Glass City, after the many glassmakers that set up here in the 19th century. Sept. 2, 2022, at 12:30 p.m. 24 Top Weekend Getaways From Chicago. Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle. 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. 506 miles east of Chicago: Upper - Kettle Creek State Park. 1 hour 30 minutes from Chicago (88 miles). Our highlights: From Thanksgiving onwards, enjoy a Reveillon Dinner a local tradition which now sees restaurants across the city offering seasonal Creole-inspired food all through December. Fennville has a few quirky local museums and things to see. 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! 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. If you want to encourage a little less screen time during the summer break, take your family to explore the great outdoors in a Budget rental. LazyTrips is a trading name of Uncle Bob Media Ltd. 2 hours 50 minutes from Chicago (180 miles). 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. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here. 2 hours 20 minutes from Chicago (130 miles). The Indian Museum of North America is nearby too. Of course, there are two sides to every story, and a few miles from Mount Rushmore you can visit the Crazy Horse Memorial. Thanks 2643 Illinois Route 178. It's also a great place to enjoy fabulous snow-based activities - the temperature usually sits around freezing and the area experiences heavy snowfall, so conditions are perfect. 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. 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. 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. 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 can even ride across the river on the Chain Ferry, one of the last remaining in America. Head across the border to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake.

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