If you want to get better scenery, you can always cut across to the Mississippi and drive up the Great River Road (see #18 above). Just after St Joseph, turn off onto I-196 where the interstate divides, and carry on north along the shore until you reach Saugatuck. Around 20 miles south of New Glarus and a little closer to Chicago is the city of Monroe. 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. We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,. From wherever you're starting in Chicago, pick up I-90 E and follow it out of the city then right the way across Indiana passing La Porte and Shipshewana. If your time is limited, take your sled and enjoy a free downhill ride at one of the several hilly public parks in the city. For amazing views of the snow-covered landscape, head up the Skylon Tower. 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. Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle. 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. The capital of Wisconsin is often overlooked in favor of its bigger brother Milwaukee 80 miles east. Many visitors head to Denver en route to the Rockies, which are right on your doorstep if you're staying in the city. LazyTrips is a trading name of Uncle Bob Media Ltd. Our highlights: The nation's capital is a fantastic place to visit during the holiday period. This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place. To get to Louisville from Chicago, you will need to drive the length of Indiana until you reach the Ohio River - St Louis is right across the John F. Kennedy Memorial Bridge. Also B&Bs. Visit in early February when the Winter Carnival comes to town and you can see firework displays or catch a fun ride on one of the resort's snow groomers. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. 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. The cheese fondue is right up there on our list of the best foods in the world! Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s. 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. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February. When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster. 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 check out a few live music venues. 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 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. 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. It took 14 years to complete the huge memorial sculpture at Mount Rushmore. A lot of these are built indoors so you can enjoy a weekend swimming, relaxing and going down crazy slides when everything outside is frozen! Change your settings: from RV campgrounds 300 miles from Chicago 299 miles north of Chicago: Mowe Lake - Manistique Rapid River Dispersed 297 miles northeast of Chicago: Aloha State Park 300 miles east of Chicago: Orchard View Park Cuyahoga County Fairgrounds 301 miles southeast of Chicago: ETA: 10+ hours with couple of short breaks. 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. Combined with St Paul, the two merged metro areas are known as the Twin Cities and are one of the largest in the Midwest. As you can see, there are still plenty of wintery attractions to enjoy in the city, just wrap up warm and see where your trip takes you. You can see how every aspect of the village life would have been complete with the blacksmith shop, school and church buildings. Nicknamed the Forest City due to the area's verdant woods and rivers, Rockford is also known as the Screw Capital of the World. Ride down the Kalamazoo River on a paddle steamer, explore the lakeshore and river in a kayak, or charter a yacht. 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 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. 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. Just after London, the road merges with ON-403, which will take you right into the center of Toronto. Head across the border to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. 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. Get a full list of up to 500 cities nearby Chicago. The festival also hosts many fun events. 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. 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! Bonus: Right through January you can enjoy the Icewine Festival, which celebrates this delicious local tipple. 3 hours 20 minutes from Chicago (190 miles). Chicago is a fantastic hub for history, architecture, gastronomy and sports. You can get a tour of the mansion and explore the vast grounds which include 620 feet of shoreline. 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. 4 hours 30 minutes from Chicago (300 miles). Flight $$$: $500. Beer and baseball are the two things the city is particularly known for. A new report shows the most dangerous cities in the USand the safest places. If you'd like to take a little shopping excursion, Nashville (IN) has a great many galleries and artisan shops. 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. The forest includes a remarkable 289,000 acres of nature adventures to experience. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. 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. After around 250 miles of driving you'll cross the Maumee River then turn off onto I-75 heading towards downtown Toledo. Southern Illinois Distance: 6-hour drive Southern Illinois has a hilly landscape and a rural vibe. If you're visiting later in the season, check out Winter Restaurant Week. You could come to Cedarburg on a long day drive, but it's really perfect as a weekend getaway destination. Though it was longer drive but not bad. After heavy rainfall - this is also the perfect time for viewing colorful wildflowers. 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 . 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. 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. The Indian Museum of North America is nearby too. The laid-back, pretense-free. 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. 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. Back in town, tour the River Arts District on foot to meet artists at work in their studios. 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. About 12,000 acres of lakes, sand dunes and oak savannas are wide open for exploration, including ice fishing, skating, sand dune sledding, fat tire biking and snowman building. If you're able to visit mid-week, you'll probably find the slopes are quieter. It's a popular place to visit, so book lift passes in advance if you know when you're travelling. The museum also contains an extensive selection of art by well-known artists and has a collection of Native American Art. 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! 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. Why visit? It's also a popular LGBTQ destination. Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races! 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. You can also enjoy a number of holiday markets, to really get you into the festive spirit. Once you've arrived in Philadelphia, you can ice skate beside the Delaware River at Winterfest, then warm up with a hot chocolate - or something stronger - with a view out across Benjamin Franklin Bridge. Back in the city, entry to the world-class Toledo Museum of Art is free all year round. Rockford is the largest city in Illinois outside Chicagoland (the Chicago metropolitan area). And of course, the Wizarding World of Harry Potter comes into its own during the winter. 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. The capitol building and a few great museums are definitely worth seeing - the Madison Museum of Contemporary Art and the Chazen Art Museum both have huge collections spanning different styles and time periods. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city. Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. 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 . If you're in the city for Christmas itself, head out along River Road on Christmas Eve, where you'll see bonfires lit on the night of the 24th so that Papa Noel can find his way from Baton Rouge to New Orleans. Save 1. 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. 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.
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