Ride down the Kalamazoo River on a paddle steamer, explore the lakeshore and river in a kayak, or charter a yacht. 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. To help you make the most of this great drive, we've set out the best routes and places to stop . Car production moved to other cities in the US, factories in Asia and Mexico and large blocks of Detroit became ghosts of their own past. 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. A complete circle of Lake Michigan to Mackinac Island, READ MORE - Road trip from Chicago To Mackinac Island, Asheville is the perfect gateway to the Blue Ridge Mountains, READ MORE - Road trip from Chicago to Asheville, READ MORE - Road trip from Chicago to Mount Rushmore, Denver is the gateway to Rocky Mountain National Park, READ MORE - Road trip from Chicago to Denver, Road trip from Chicago to Yellowstone National Park. So if you are already in Chicago then you should explore these 12 best road trips from Chicago. Just before Cleveland, merge onto I-80 and follow this all the way across Ohio, Pennsylvania and New Jersey before crossing into Manhattan via George Washington Bridge. Fly from Chicago to Columbus, Ohio, for $167 round trip The most costly of our cheapest air fares from Chicago's O'Hare International Airport still comes in at an attractive $167 round trip, meaning it's now easier than ever for Illinois locals to make the quick 1.25-hour hop straight across the heartlands of the Midwest. With fast lifts, extensive ski runs and stunning views, you'll probably want to spend most of your time here on the slopes. Southern Illinois Distance: 6-hour drive Southern Illinois has a hilly landscape and a rural vibe. Asheville is packed full of history, but the modern city has a distinctly creative vibe that makes it really unique. Take a carriage ride through Central Park, which is even more magical when there's snow on the ground. 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! It was an early adopter of snowmaking technology in the 1950s. Many of the events and installations are outdoors, so, this being Michigan, chances are you'll be enjoying them in the snow. 2 hours 30 minutes from Chicago (147 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! 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: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions. 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. You can easily fill a weekend here with fun and varied runs. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh. 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. Our highlights: The World of Winter Festival usually starts in the first week of January, and as well as ice sculptures you can see interactive installations from artists all over the world, with walking tours taking you through some of the outdoor art highlights. 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. You will pass through the cities of Milwaukee, Green Bay, Traverse City and Grand Rapids which are all worth going to in their own right. Millions of years of geologic changes are reflected at the Garden of the Gods in But that's just the welcome mat to this SoCal haven. The forest includes a remarkable 289,000 acres of nature adventures to experience. 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. You can even ride across the river on the Chain Ferry, one of the last remaining in America. 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. Our travel tips: Book in advance if you're visiting Winterfest, as the town gets really busy. The cheapest month to fly from Chicago is January. 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. Remember that Minneapolis can get cold, and even feel cool in the summer. 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. 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. 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. Through the rest of the season, winter sports fans will love to ski at Wilmot Mountain, a popular ski resort with over 20 ski runs suitable for a wide range of abilities. You'll finally turn off the interstate at Rapid City, joining US-16 for the last few miles of your drive to Mount Rushmore. From here, follow I-196 further around the lake shore. As Christmas gifts go, a whole city is one we wouldn't mind receiving! 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. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades. 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. You will pass by some imposing homes and quiet lakeside neighborhoods with picturesque cafes. 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. 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. Make sure you grab some food at the Root beer Stand. As with everywhere in Wisconsin, the food and drink scene takes center stage. The parade brings together dragons and lions dancing through DC's streets, as well as drummers, dance troupes and firecrackers - it's a real feast for the senses. to the Bacon and Brews event where you can sample fine bacon and beer pairings, there is always something happening. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. If you have time to head out of town, make your way to Tampa to see Christmas Town at Busch Gardens. 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. The fast ferries will take under 20 minutes to get you there. 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. Founded in 1778, Louisville is a really amazing mix of old and new. Kentucky might only provide about a twenty-degree warm-up, but during the super cold times, those twenty degrees can feel like heaven. PC . 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. A particular highlight in Muskegon is its Luge track, which is open to the public. ETA: 10+ hours with couple of short breaks. This is the place to come for a great resort experience, with lodges, bars and of course, slopes, all in one place. 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. The Indian Museum of North America is nearby too. Our highlights: Boyne Mountain is primarily a ski resort, so take to the slopes and explore more than 415 acres of ski runs. Why visit? Here are several interesting options that make a great family road trip and all within easy driving distance of Chicago. Best for: Family fun or a romantic rendezvous. Utica, IL 61373. 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. 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. For amazing views of the snow-covered landscape, head up the Skylon Tower. 1 hour 35 minutes from Chicago (83 miles). Chicago is a fantastic hub for history, architecture, gastronomy and sports. 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. Boyne Mountain Resort Distance: 5-hour drive Michigan winters are best captured with the ski resort of Boyne. 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. 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. Our highlights: Roll back 100 years and one of the biggest draws of Lake Geneva, WI, wasn't its snow, but the ice! This leads you eventually onto I-95, which you'll follow south to Savannah. Why you should visit: Mild weather and weeks of flamboyant parades makes New Orleans the perfect contrast to snowy Chicago. There are a number of museums to explore - some of the main ones located along the Museum Row. The City of Lakes is a bustling hub of activity - 6 of the Fortune 500 companies are headquartered here and it's known as a major cultural and arts center. 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. Restaurants like the Grove and Terra serve locally sourced ingredients which means the menu changes throughout the year. Everything from cow's milk to goat and sheep milk is used and there are imitations of European cheeses and unique local flavors available. The Warmest Place in Chicago. Leave time to explore. After heavy rainfall - this is also the perfect time for viewing colorful wildflowers. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. It's a great way to spend time with friends, get into the festive mood, as well as to find some unique Christmas gifts. The museum also contains an extensive selection of art by well-known artists and has a collection of Native American Art. 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. On the south side of the lake is the Black Point Estate. After a rapid period of growth through the first two thirds of the 20th century, Detroit suffered an economic collapse and a massive decline since the 70s. Afterwards, take some time to admire the cathedral's architecture - and see if you can spot the Darth Vader gargoyle. Bonus: Early in February Lake Geneva's Winterfest bursts into action, with an ice sculpting competition and snow races! 2 hours 30 minutes from Chicago (155 miles). 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. Don't worry about missing out on too much of that winter snow either - your drive will take you through the Appalachians so you can take in some stunning views as you make your way south to Georgia. Starved Rock State Park is just 100 miles southwest of Chicago, offering an ideal spot to enjoy nature with more than a dozen sandstone canyons along with beautiful waterfalls that are especially powerful in the spring. The name gives away what this place is all about - everything here stems from Holland's Dutch origins. 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. Lake ice was harvested and taken to nearby towns and cities - it was big business here as late as the 1940s. From Chicago To Driving Time: Lake Geneva, WI: 1 hour and 30 minutes: Galena, IL: 2 hours 45 minutes: Kohler, WI: 2 hours and 20 minutes . All things considered, it's easy to see why Niagara-on-the-Lake's Icewine is such a special product to try during your visit. How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville. 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. 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 temperatures surpassed the 136-year-old . The capital of Wisconsin is often overlooked in favor of its bigger brother Milwaukee 80 miles east. One of the great things about Toledo is that although it's one of the largest cities in Ohio, visiting is relatively straightforward. 8 hours 40 minutes from Chicago (530 miles). 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. 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. Thanks 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. 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. 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. Like Chicago, Saugatuck is also located on the Lake Michigan shore, but it couldn't be more different. But is it worth a daytrip to an obscure Chicago suburb? The laid-back, pretense-free. 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. Adrenaline junkies can ride ziplines in several places around Asheville, take a rafting trip or go canyoneering. All that snow means that you can ski in the area around Asheville. Although it serves a lot of dishes to serve American tourist tastes, you can try the Wienerschnitzel (pan fried breaded veal cutlet) or the cheese fondue (dipping pieces of bread into molten cheese). 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. Here you can join in with the 9-day Winter Festival (late January). Other activities include spending the day at Kalapaki or Po'ipu beaches, setting. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city. There are 4 large waterpark resorts (Kalahari, Great Wolf, Chula Vista and the Wilderness) and around 20 in total with more being constructed. 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. 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. 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. 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. Named after the tall cedar trees, it is particularly well known for its lush forests that cover the hills around Cedarburg. For something a little different, visit Wings Over the Rockies Air and Space Museum to see a large collection of planes, including many vintage models. 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. 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. 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. 1 hour 20 minutes from Chicago (80 miles). Heading towards Lake Michigan, you will find the small harbor village of Saugatuck. The main attractions are the two major parks - the Starved Rock State Park and the Matthiessen State 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. 8. 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). 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! As well as the festive markets that take place across the city, where you can admire beautiful decorations and gifts or enjoy some fabulous food and drink, you can take in a carol concert at the National Cathedral. As you make your way from Chicago to Philadelphia, make sure to fit in a visit to Bethlehem, PA, too. Also running from Thanksgiving right up to New Years Day is Celebration in the Oaks. You can see how every aspect of the village life would have been complete with the blacksmith shop, school and church buildings. Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest! 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. The small town of Oglesby, home to 3,600 people, is renowned for its natural beauty. Our travel tips: Although temperatures are at or below freezing through most of the winter, you're not always guaranteed snow in Toronto, so be prepared that you might miss out on the insta-perfect images of this particular winter road trip. 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. Canada produces a significant proportion of the world's Icewine, a dessert wine created from grapes left on the vine to freeze before being harvested. Outside of the downtown Fennville, you'll find rolling fields and orchards that are both pretty and make some great food. 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. 1 hour 30 minutes from Chicago (88 miles). 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. Then, check out the Christmas Village or the Made in Philadelphia Holiday Market. Get a full list of up to 500 cities nearby Chicago. 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. Not far away, Wind Cave is one of the world's longest. Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. We'd recommend booking ahead to guarantee your entry, especially if you're visiting at busy times,. 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 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. 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. 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.
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