The hip city has a lot of things to see and experience. Ride down the Kalamazoo River on a paddle steamer, explore the lakeshore and river in a kayak, or charter a yacht. 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: The weather stays mild all year round in Savannah, so it's a great place to come and escape the Midwest chill. 12 Short & Long Road Trips From Chicago | Budget Car Rental There are a few museums and sights to see - the Grand Rapids Public Museum and the Art Museum are both worth going to. Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle. Once you get to halfway point, you should spend a day or longer on Mackinac Island. 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). This after-dark spectacle sees City Park lit up with more than a million lights. Follow the Great River Road as it twists and turns and you will be rewarded with great views the entire way. Lake Monroe is the state's largest man-made lake. 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. Follow this road all the way across Illinois to Davenport, where you'll cross over the Mississippi River which forms the border between Illinois and Iowa. 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. First is the village of New Glarus. The best thing about Grand Rapids, however, is the food and the drink. This means you probably won't see the grape harvest unless you're out in the vineyards at night - pickers tend to work by hand to make sure of the most perfect harvest possible. Best for: Family fun or a romantic rendezvous. Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. The fastest way to get to Minneapolis from Chicago is to go the I-90 and I-94 route across Wisconsin. The area is also home to a number of very decent wineries. The temperatures surpassed the 136-year-old . To help you make the most of this great drive, we've set out the best routes and places to stop . New this winter, try curling. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience. Like Chicago, Saugatuck is also located on the Lake Michigan shore, but it couldn't be more different. As you'd expect, with much of the Midwest sitting under snow through the winter, the weekend trips you can take from Chicago all have a winter sports element to them. 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. So, sit back, relax, and learn all you need to know in planning a road . The main attractions are the two major parks - the Starved Rock State Park and the Matthiessen State Park. It's also a popular LGBTQ destination. 25 Best Weekend Getaways from Chicago - VacationIdea Just after crossing the Ohio River at Evansville, turn onto I-69, continuing south on I-169 where the interstates divide. 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. It is more than 10-14 hours to get to a warm beach from Chicago. How to get there: Join I-57 and follow it south all the way to Cairo, on the Illinois/Missouri border. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well. Head across the border to see the falls from a different perspective, or visit the fabulous wineries of Niagara-on-the-Lake. Went to New York (which was fun) so that is covered. 8. 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. Southern Illinois Distance: 6-hour drive Southern Illinois has a hilly landscape and a rural vibe. Then, take I-40 from Knoxville to Asheville then join I-26 south passing Spartanburg and Columbia. 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. Cool down in warmer weather by riding the natural waterslide at Sliding Rock. If you're looking for unique and often hand-made gifts for family and friends, you'll find plenty of choice here. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights. Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota. 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. 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 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. Or if you're feeling more active, there are sledding slopes in the park too. 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. How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. 2 hours 20 minutes from Chicago (130 miles). A little further north from Chicago than Milwaukee is the town of Cedarburg. There are 4 large waterpark resorts (Kalahari, Great Wolf, Chula Vista and the Wilderness) and around 20 in total with more being constructed. If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. 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. 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. 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. One of the best places to visit in Illinois, this state park features 18 canyons and 13 miles of hiking trails to explore. You must try the Glarner Stube restaurant in town. Plus, you can fill yourself with festive cheer with a visit to the traditional market at Love Park's Christmas Village, or a stroll through streets filled with fabulous Christmas lights. 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. 1 week road trip within 10 hours or so of Chicago - Tripadvisor One interesting place to visit is Frank Lloyd Wright's Laurent House. 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. Book a fantastic treatment or simply hang out in the sauna, steam room or heated outdoor pool to enjoy the mountain vibes from a different angle. Places to visit about 9 hours from Chicago - Within Hours 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. I am actually down for anything, just to get some fresh air and get out of the city. At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. With art, culture, caf patios and waterfront dining, Toledo is a great short trip if you want a change of scene from Chicago. Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. Cheap Flights from Chicago from $36 - KAYAK Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. I-80 is a notoriously busy road, with heavy commercial traffic and few landmarks of interest. How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville. 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. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain. 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. When it's complete the statue of Crazy Horse will be taller than the presidents at Mount Rushmore. Weekend Getaways from Chicago: Market Street Inn - 3 hours . 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. As with everywhere in Wisconsin, the food and drink scene takes center stage. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south. (Getty Images) Known as . You can easily fill a weekend here with fun and varied runs. Expect fabulous parades, live music and all-night parties. The self proclaimed moniker comes from the factories in the city that supply the rest of the country with various kinds of fasteners, screws, nuts and bolts. 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! Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions. You can also snowshoe, tube or skate if you want a break from the slopes. 15 hours 10 minutes from Chicago (960 miles). Tickets for guided tours at Wind Cave National Park often sell out, so advance booking is recommended, especially if you're travelling in the busier summer months or over holiday periods. 506 miles southeast of Chicago: Toe River Campground. Report Ranks America's 15 Safest (And Most Dangerous) Cities - Forbes How to get there: Follow I-90/I-94 north out of Chicago, then continue north on I-94 when the interstate divides. 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. 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. The museum also contains an extensive selection of art by well-known artists and has a collection of Native American Art. 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. It features more than 100,000 lights and is the largest pipe organ in the world. Whether you're looking for an active break or a peaceful boat trip, there are plenty of opportunities to get out onto the water. The cheapest month to fly from Chicago is January. You'll finally turn off the interstate at Rapid City, joining US-16 for the last few miles of your drive to Mount Rushmore. 1. 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. 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. Then there's dozens of amazing natural parks to explore, especially towards the northern tip of the lake. As you make your way from Chicago to Philadelphia, make sure to fit in a visit to Bethlehem, PA, too. Beer and baseball are the two things the city is particularly known for. Distance from Chicago: 150 miles north, 2.5-hour drive This charming little hideaway about 30 minutes west of Sheboygan is often overlooked but shouldn't be. The 10 Cheapest Flights from Chicago | Hopper Instead, workers used dynamite to shape most of the sculpture. With large distances to cover, some of the early pioneers of flight lived and worked in this part of the country and you can also find out about the former Air Force base where the museum is located. 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. 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. There are also several events to mark Dia de los Muertos in late October and early November. The first week of December is particularly busy, but many travellers report that the crowds and prices calm down a little mid-month. Otherwise you can find a selection of different cheese styles and types. Where's the warmest, sunniest place in Chicago during the winter months? 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. Back in town you'll get beautiful winter views over icy Lake Michigan. Weather at the end of March can be iffy. 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. This idyllic shoreline in Michigan's southwestern corner stretches from the Indiana border to the town of Sawyer. Everything here is about cheese. NOTL is also a really charming little town, and while you're here you might like to take a horse-drawn carriage ride through its historic streets - a wonderfully atmospheric way to travel through the snow-covered streets. Distance from Chicago: 353 miles northeast, five-hour drive Why it made our list: Sprawling over 850 acres, the Midwest's largest ski resort offers everything from skiing and snowmobiling to. 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. Asheville is packed full of history, but the modern city has a distinctly creative vibe that makes it really unique. Heading towards Lake Michigan, you will find the small harbor village of Saugatuck. Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. The city was offered up to President Lincoln as a Christmas Gift during the Civil War. San Diego San Diego boasts 260 sunny days a year, miles of rugged beachside and barking seals. The two-lane road winds its way through the mountains, with plentiful overlooks and hiking trails to stop and explore. 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. Muskegon Farmers Market operates indoors on Saturdays through the winter so you can warm up and stock up on some fabulous local produce. The town of Holland sits along the length of Lake Macatawa that flows into Lake Michigan. 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! Why you should visit: You can see the Nation's Christmas Tree, a century-old tradition in the city - it's illuminated from early December in a popular ceremony that for many marks the start of the holiday season. 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 travel tips: Parts of the city get extremely crowded in December, and accommodation prices rise accordingly. 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. Parking can be difficult, especially in the summer months when hundreds of visitors head to town. 1 hour 35 minutes from Chicago (83 miles). Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. Two different types of ski lifts were invented here - so when you ski here in modern times you'll be following the lead of some of the country's ski pioneers. If you're visiting later in the season, check out Winter Restaurant Week. 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. 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. Also running from Thanksgiving right up to New Years Day is Celebration in the Oaks. Your email will not be provided to third parties. Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village. After Gainesville, join the Florida Turnpike which takes you the last stretch of the drive into Orlando. There's another dozen smaller lakes dotted around which breaks up the city into smaller neighborhoods and adds a lot of character. This waterfront city is the only destination on this list that takes you to another of the Great Lakes. The Anheuser-Busch Brewery and Biergarten are the home of Budweiser but there are loads of small local breweries where you will get a more authentic experience. 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. 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. 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. 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. Why visit? The detour will add around two and a half hours so bake that into your planning and consider stops along the way. The local Fermentorium brewery has some 24 different beers on tap - not too shabby for a local place! How to get there: Follow the interstate east out of Chicago and then continue north, keeping Lake Michigan on your left. After around an hour, exit at Kenosha and pick up WI-50 west which will take you to Geneva. 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! Our highlights: The nation's capital is a fantastic place to visit during the holiday period. 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. 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. Road Trip from Chicago to San Francisco - LazyTrips You'll find yourself in a warm weather wonderland with trees, lights, skating and fireworks. The biggest ski area in the state is perfectly set up for skiers, with fast lifts and dozens of trails to follow. 6 hours 30 minutes from Chicago (430 miles). But did you know that every single participant has to wear one? You can see how every aspect of the village life would have been complete with the blacksmith shop, school and church buildings. 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. 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 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. 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. 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. Founded in 1778, Louisville is a really amazing mix of old and new. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. 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. It eventually turns inland to take you right to Grand Rapids. 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. How to get there: Head north on I-90 out of Chicago then join I-94. Join I-90 E to head out of Chicago then merge onto I-94 to continue to follow the shore of Lake Michigan. 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. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own. Drive time: 2 hours from downtown. Record-breaking April 13: Chicago snaps 136-year-old warm weather With many travelers heading to Asheville to see the stunning display of foliage in the fall, we'd recommend booking ahead to guarantee your choice of accommodation at this time of year. ETA: 10+ hours with couple of short breaks. 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. Chicago is a fantastic hub for history, architecture, gastronomy and sports. 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. This popular vacation town is also less crowded in winter compared to the summer months. 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. St Julian Winery or Lemon Creek are great to visit and well located just off the interstate. 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. 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. You also don't have to book attractions weeks in advance, and you can find reasonably priced accommodation in the downtown area.
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