Why you should visit: This beautiful little lakeside town hosts a magical Christmas market every year. A few of the upcoming options on our road trip list are all due north in Wisconsin. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. 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. You should definitely visit New York in winter so you can say you've experienced them all first-hand. 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. The museum also contains an extensive selection of art by well-known artists and has a collection of Native American Art. 8 hours 40 minutes from Chicago (530 miles). The festival also hosts many fun events. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well. For summer fun during the winter months, Grizzly Jack's Grand Bear Resort is the place to be. You can see Cinderella's Castle made even more magical at Walt Disney World, or visit EPCOT's International Festival of the Holidays to take a whistle-stop tour around the world's traditions. Other activities include spending the day at Kalapaki or Po'ipu beaches, setting. From here, pick up I-76 and follow it straight down to Denver. You can also enjoy a number of holiday markets, to really get you into the festive spirit. 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. 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. From jazz to soul, St Louis has been one of the most prominent musical cities in the US - Tina Turner and Scott Joplin started their careers here among others. 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. 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 name gives away what this place is all about - everything here stems from Holland's Dutch origins. 809 Civic Center Dr., Niles; 847-972-2540 or kingspa.com. So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers. There are festivals throughout the year from the world's largest Bratfest (you can eat a lot of sausages here!) Instead, workers used dynamite to shape most of the sculpture. You'll finally turn off the interstate at Rapid City, joining US-16 for the last few miles of your drive to Mount Rushmore. 4 hours 20 minutes from Chicago (300 miles). A new report shows the most dangerous cities in the USand the safest places. The Louisville Muhammad Ali Center and the Frazier History Museum will keep you busy! Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions. Only an hour away from downtown Chicago, Indiana Dunes became the newest National Park in the United States in 2019. You can easily visit on a short day road trip from Chicago, but if you want to explore the different trails and get away from it all, a weekend trip might work better despite being so close. Leave time to explore. 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. 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. 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. 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. It's a popular place to visit, so book lift passes in advance if you know when you're travelling. Alternatively, if you'd prefer to just relax and unwind, maybe after a tour round the Christmas market or some time on the ice rink, head to the luxurious Aspira Spa to round off your trip. 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. Beer and baseball are the two things the city is particularly known for. 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. If you're able to visit mid-week, you'll probably find the slopes are quieter. If you're not visiting for the Derby, it's best to avoid going in May as hundreds of thousands come for the event and prices go sky high. 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. Constructed between 1906 and 1907, the Conservatory was conceived and designed by Chicago's West Park Commission's general superintendent and chief landscape architect, Jens . Make sure you grab some food at the Root beer Stand. Originally a very rural part of Michigan with a few small towns and their corresponding harbors on the lake, the area has grown into a popular tourist destination. Choose from a lodge room, suite, 4-bed or 8-bed luxury cottage, ideal for multi-generation or multi-family groups. Around 20 miles south of New Glarus and a little closer to Chicago is the city of Monroe. You might not have heard of it, but the United States has its very own Gevena Lake and it's located in Wisconsin, just across the border from Illinois. Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December. Once you arrive at Mount Rushmore, you can also spend time exploring the stunning Black Hills and surrounding area. This Mom n pop classic fast food diner has been in Oglesby since 1955 and serves top notch root beer floats and burgers. Chicago is a fantastic hub for history, architecture, gastronomy and sports. Make sure you check out a few live music venues. 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. You have a few to choose from, including the outdoor Downtown DC Holiday Market, the Swedish Christmas Bazaar in Georgetown, and the Heurich House Museum Christkindlmarkt. The high temperatures that hit Chicago Thursday broke a record that stretched all the way back to 1887, according to the National Weather Service. During the daytime, Saugatuck Interurban Transit Authority provides an on-demand bus service which takes you to your destination of choice within the local area for just $1. The area is also home to a number of very decent wineries. 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. 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. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here. Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. First is the village of New Glarus. Sept. 2, 2022, at 12:30 p.m. 24 Top Weekend Getaways From Chicago. 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. Head across the border to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. But that's just the welcome mat to this SoCal haven. Join I-90 E to head out of Chicago then merge onto I-94 to continue to follow the shore of Lake Michigan. Staying by the lake, seeing as the water freezes over, you can go ice fishing here with a guide, who can provide all the equipment you need if you don't have your own. 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. Things to do on Kauai include exploring the Waimea Canyon, Kkee State Park, Na Pali Coast and the Kalalau Trail. 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. Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s. 1 hour 35 minutes from Chicago (83 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. 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. 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. 506 miles southeast of Chicago: Toe River Campground. 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. 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. This popular vacation town is also less crowded in winter compared to the summer months. Although this is a long drive, it's a really straightforward one. No need to get on the flight. Plus, if you're in the market for some Christmas shopping you can take your pick of fabulous department stores, designer brands and boutique sellers. 1. Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. You can easily visit for a day or stay the night to see more of the local sights and museums. The main attraction is the carved cliff face featuring four Presidents of the United States. You can get a tour of the mansion and explore the vast grounds which include 620 feet of shoreline. Many visitors head to Denver en route to the Rockies, which are right on your doorstep if you're staying in the city. One is the Forever Curious Children's Museum - a non-profit organization created to spark a love for learning in kids of all ages. Also running from Thanksgiving right up to New Years Day is Celebration in the Oaks. After crossing the border into Canada, the road becomes ON-401. 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. 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. 5 hours 40 minutes from Chicago (350 miles). There are a lot of activities for children - special rides and a petting zoo so bring the family and enjoy a great weekend out of the city! There's another dozen smaller lakes dotted around which breaks up the city into smaller neighborhoods and adds a lot of character. PLAN YOUR TRIP: Visit Fodor's St. Maarten Guide Jo Ann. 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. The small town of Oglesby, home to 3,600 people, is renowned for its natural beauty. The cheapest month to fly from Chicago is January. 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. 2 hours 20 minutes from Chicago (145 miles). The forest includes a remarkable 289,000 acres of nature adventures to experience. Expect fabulous parades, live music and all-night parties. 3 hours 20 minutes from Chicago (190 miles). You will pass by some imposing homes and quiet lakeside neighborhoods with picturesque cafes. Bozeman, MT. Exhibits are very interactive and fun for the whole family. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet Florida sun including hourly snow flurries. Any suggestions fellas? This idyllic shoreline in Michigan's southwestern corner stretches from the Indiana border to the town of Sawyer. Weather at the end of March can be iffy. 1 hour 30 minutes from Chicago (88 miles). 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. Your email will not be provided to third parties. How to get there: Join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. At Coastal Georgia Botanical Gardens, you can follow the beautiful light trail through the magical gardens, for example, or take a holiday trolley tour or boat trip to see the city decked out in festive finery while enjoying a wonderful warm cider. The city was offered up to President Lincoln as a Christmas Gift during the Civil War. Fennville has a few quirky local museums and things to see. You can join the river at Savanna or a little further down at Clinton depending on the route you take. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park. 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. 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. Lake Monroe is the state's largest man-made lake. Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota. 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. 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. With art, culture, caf patios and waterfront dining, Toledo is a great short trip if you want a change of scene from Chicago. 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. 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. Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. 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. San Diego San Diego boasts 260 sunny days a year, miles of rugged beachside and barking seals. Hot Springs (Arkansas) Distance: 650 miles. When it's complete the statue of Crazy Horse will be taller than the presidents at Mount Rushmore. 1 hour 20 minutes from Chicago (80 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. 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. Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake. You can also go on a tour of the Cedar Creek Winery and try the local wines which might just surprise you. 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. Utica, IL 61373. When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster. Bonus: As well as being known for its winter sports, Grand Rapids is famous for its many craft breweries - in fact, it's been given the title of Beer City USA! 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. 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! Back in the city, entry to the world-class Toledo Museum of Art is free all year round. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south. Hemlock Hideaway Campground. also, you have the option of taking the ss badger car ferry across Lake Michigan to avoid traffic around the bottom of the Lake and to add an St Julian Winery or Lemon Creek are great to visit and well located just off the interstate. Also B&Bs. How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities. Our travel tips: Don't go to DC expecting reliable snowfall daytime temperatures are milder than the more northern destinations (in the mid-40 degrees Fahrenheit and above), though it still gets pretty cold at night, and snow is likely but not guaranteed in January and February. 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. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February. If you're staying overnight it's best to find accommodation with private parking. In the evenings from May to September there's also a 45-minute ranger talk which ends with the lighting ceremony. 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. For amazing views of the snow-covered landscape, head up the Skylon Tower. 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. 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. 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. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own. If you are looking for cheap weekend getaways from Chicago, this is a good place to stay. When you're ready to head into the warm, make your way to Leigh Yawkey Woodson Art Museum. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades. SBD is a respectable 2nd place, IMO, and added attractions are wine country, nice beaches, warmer water (usually) and resort options (homestead resort near glen arbor gets high marks in the MI-Fo's). There are a few museums and sights to see - the Grand Rapids Public Museum and the Art Museum are both worth going to. Sundays have a free Jazz Brunch outdoor concert series along the scenic Riverwalk. 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. Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. 605 S. Prospect St., Galena IL, 800-717-2317. 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. 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. 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. 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. 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. How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville. After Hopkinsville, join I-24 and follow it through Nashville to Chattanooga where you'll switch onto I-75 which runs all the way to Florida. It's called - you guessed it - the Cheese Country Trail System (no, really)! The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. Here you can join in with the 9-day Winter Festival (late January). Stop at the Crane Orchards to sample one of their legendary pies as you make your way around! It's all a little strange, perhaps. It's a great way to experience this historic part of the city, full of character. The first week of December is particularly busy, but many travellers report that the crowds and prices calm down a little mid-month. 1 hour 30 minutes from Chicago (93 miles). 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! 2643 Illinois Route 178. Expect congestion on the Blue Ridge Parkway, especially if you visit at weekends. Where to Stay. Toledo is known as the Glass City, after the many glassmakers that set up here in the 19th century. Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle. If it's your first time in Toronto, you'll probably want to see some of the city's sights while you're in town too. The Swiss Historical Village is a great live museum which has kept 14 buildings in the style of the original 19th century settlement. By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. 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.

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