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. 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. 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! Not far away, Wind Cave is one of the world's longest. You could come to Cedarburg on a long day drive, but it's really perfect as a weekend getaway destination. How to get there: Follow I-90 out of the city then pick up I-94 and head east towards Detroit. After heavy rainfall - this is also the perfect time for viewing colorful wildflowers. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. 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. Join I-90 E to head out of Chicago then merge onto I-94 to continue to follow the shore of Lake Michigan. This waterfront city is the only destination on this list that takes you to another of the Great Lakes. You'll find yourself in a warm weather wonderland with trees, lights, skating and fireworks. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. Note that to enjoy all the attractions Niagara Falls has to offer, you might need to factor in crossing the US/Canada border so make sure you have any paperwork you need (dependent on nationality). If you're having issues using the site, please enable JavaScript and refresh your browser. 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. At Denver Art Museum you can see another collection dedicated to the heritage of this part of the country, as the Petrie Institute for Western American Art is housed here. Once you get to halfway point, you should spend a day or longer on Mackinac Island. Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago. How to get there: This is a really simple trip just follow I-90 all the way from Chicago. This makes for one of the best road trips from Chicago. Ice sculptors spend nearly 2 months creating spectacular icy towers and turrets which are especially beautiful when they're illuminated at night. The area is also home to a number of very decent wineries. 1 hour 35 minutes from Chicago (83 miles). 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. 2 hours 20 minutes from Chicago (130 miles). 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. With fast lifts, extensive ski runs and stunning views, you'll probably want to spend most of your time here on the slopes. 13 hours 40 minutes from Chicago (925 miles). Like Chicago, Saugatuck is also located on the Lake Michigan shore, but it couldn't be more different. Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own. Savannah is a great place to visit all year round but come in winter to enjoy this fabulous city without the summer crowds or humidity. How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. Skate beneath the massive Christmas tree at the famous Rockefeller Ice Rink, before heading up to the Top of the Rock to take in the view of New York in the snow. I am actually down for anything, just to get some fresh air and get out of the city. Oglesby and its neighbor Utica lie nestled into a curve of the Vermilion River and is perfect for exploring some of the best outdoors in Illinois. 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. Expect fabulous parades, live music and all-night parties. 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: Some of the outdoor activities that Niagara Falls is famous for, notably the Maid of the Mist boat cruise, do not operate in winter, but as we've identified, there are plenty of other ways to enjoy views out across the falls. If St Louis Cardinals are playing, it's worth going if you can get your hands on some (expensive) tickets - they are one of the most successful baseball teams of all time and baseball is the number one sport in town. To make the most of it, though, you really should consider stopping the night and exploring the local beer scene. It features more than 100,000 lights and is the largest pipe organ in the world. RV campgrounds 500 miles from Chicago. Flight $$$: $500. That way, current and future visitors will be guaranteed the same fabulous experience of NOLA's longstanding and unique traditions. How to get there: Head east out of Chicago on I-90, keeping Lake Michigan on your left, then continue on I-94 as far as Lake Joseph. A little further north from Chicago than Milwaukee is the town of Cedarburg. 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. Then, for a unique and romantic end to your trip, you can even take a horse-drawn sleigh ride through the city. 1 hour 20 minutes from Chicago (80 miles). Kentucky is only about seven hours from Chicago. 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. The track is open to kids as young as 8 so bring the whole family and see if any of them catch the sliding bug. Millions of years of geologic changes are reflected at the Garden of the Gods in 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! 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. Our highlights: Florida is the warmest part of the continental US through the winter - perfect for escaping the sub-zero temperatures of the Midwest! 605 S. Prospect St., Galena IL, 800-717-2317. 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. 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. Combined with St Paul, the two merged metro areas are known as the Twin Cities and are one of the largest in the Midwest. Follow the Great River Road as it twists and turns and you will be rewarded with great views the entire way. 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. For the perfect post-ski wind down, visit the Spa at Boyne Mountain before you head home. Overnight on the California Zephyr gets you to Denver where the weather is just as cold as Chicago but you'd be in a cosmopolitan city. 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. After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain. Motor City is the second largest city in the Midwest after Chicago and is worth making the drive for. As well as being beautiful, the crowds that flock to Niagara Falls are slightly less during winter. The two-lane road winds its way through the mountains, with plentiful overlooks and hiking trails to stop and explore. Exhibits are very interactive and fun for the whole family. Other activities include spending the day at Kalapaki or Po'ipu beaches, setting. The main attraction is the carved cliff face featuring four Presidents of the United States. The Swiss Historical Village is a great live museum which has kept 14 buildings in the style of the original 19th century settlement. Also, although this isn't a ski destination like some of the other trips, you can still enjoy some winter sports in Elkhart Lake. One is the Forever Curious Children's Museum - a non-profit organization created to spark a love for learning in kids of all ages. 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. Went to New York (which was fun) so that is covered. It's the perfect place for a romantic getaway - wrap up warm and enjoy snowy views over the beautiful city and lake before warming up with a hot chocolate and a loop or two around an outdoor ice rink. 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. 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. 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. It is more than 10-14 hours to get to a warm beach from Chicago. 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. If you want to head across the border to visit Niagara-on-the-Lake make sure to pack the required travel documentation, and allow extra time to make the border crossing, especially if you're heading across Rainbow International Bridge. The first week of December is particularly busy, but many travellers report that the crowds and prices calm down a little mid-month. 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. Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December. 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. Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. 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. From here, turn onto Route 31 which takes you on to Muskegon. At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. 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. 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. Seeing as you've travelled from one Great Lake to another, a visit to the National Museum of the Great Lakes seems like a good place to start when you arrive in Toledo. After crossing the border into Canada, the road becomes ON-401. 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. 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: 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. 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. How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. Fennville has a few quirky local museums and things to see. Otherwise you can find a selection of different cheese styles and types. It makes sense to book ahead if you're planning on visiting between Christmas day and New Year, or weekends during January and February. Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village. If you're feeling active, there are places where you can sled on the frozen sand dunes. Add in beautiful beaches all over, some big sand dunes, including the Indiana Dunes National Park and the pretty towns of Harbor Country. 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 maximize your Swiss experience, then combine your road trip to New Glarus with a stop in Monroe - the Swiss Cheese Capital of the USA. It was founded by a group of Swiss settlers from the Swiss canton of Glarus in 1845. You can enjoy spending time outside, take a walk along the river, or just relax in one of Savannah's beautiful squares - the polar opposite of a Chicago winter. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience. Instead, workers used dynamite to shape most of the sculpture. Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. 4 hours 30 minutes from Chicago (280 miles). How to get there: Follow I-90 east across Indiana. Bonus: Macy's Christmas Light Show another of the city's festive traditions is a record breaker! 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. 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. You can also enjoy a number of holiday markets, to really get you into the festive spirit. 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. Plus the views from the vineyard are sublime! High season is considered to be June and July. Bonus: If you're here before the holidays, get into the festive spirit at the Distillery District Christmas Market, which runs from mid-November until New Year. Founded in 1778, Louisville is a really amazing mix of old and new. 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. 2 hours 50 minutes from Chicago (180 miles). After around an hour, exit at Kenosha and pick up WI-50 west which will take you to Geneva. 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. Our highlights: There are so many memorable festive moments to fit into a winter trip to New York City, it's hard to know where to begin. 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 Indian Museum of North America is nearby too. 17 hours 30 minutes from Chicago (1,130 miles). Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake. First is the village of New Glarus. 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. Why visit? 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. 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. 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. 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. 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. The Great River Road runs the length of the Mississippi river and you can drive part of it on a scenic road trip from Chicago. Here are several interesting options that make a great family road trip and all within easy driving distance of Chicago. 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. In the evenings from May to September there's also a 45-minute ranger talk which ends with the lighting ceremony. This leads you eventually onto I-95, which you'll follow south to Savannah. Make sure you grab some food at the Root beer Stand. Although this is a long drive, it's a really straightforward one.
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