605 S. Prospect St., Galena IL, 800-717-2317. 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. 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. Bonus: The capital hosts a fabulous Lunar New Year Parade in January or February depending on when the new year begins. 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. Cheap Flights from Chicago from $36 - KAYAK 5 Winter Road Trip Ideas to Warmer Destinations - Auto Lab Boyne Mountain Resort Distance: 5-hour drive Michigan winters are best captured with the ski resort of Boyne. 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. 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. This waterfront city is the only destination on this list that takes you to another of the Great Lakes. Still under construction, this monument is dedicated to the Lakota leader who fought against the federal government to try and protect Native American land from being seized. 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. These will carry you up to a quarter of a mile across the resort's valleys, giving you a bird's eye view of your stunning surroundings. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip. 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. 3 hours 20 minutes from Chicago (190 miles). 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. A particular highlight in Muskegon is its Luge track, which is open to the public. The city's popular Longwood Gardens is transformed with amazing lights and live music, so it makes a great place to spend some time after the sun goes down (which happens early in winter!). When it's time to warm up, head back into town to Old Sugar Distillery, a small local spirits producer, for a warming taster. Join I-90 E to head out of Chicago then merge onto I-94 to continue to follow the shore of Lake Michigan. And one of the three sections of the Hoosier National Forest is immediate to this area. Other activities include spending the day at Kalapaki or Po'ipu beaches, setting. 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. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades. 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. Alternative options are the Frederik Meijer Sculpture Park and the Fish Ladder Park. Ride down the Kalamazoo River on a paddle steamer, explore the lakeshore and river in a kayak, or charter a yacht. 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. 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. Our highlights: As you'd expect, the main draw of Muskegon in winter is Muskegon Luge Adventure Sports Park. There are two giant lakes right in the middle of the city, either side of downtown which creates a uniquely relaxed vibe. The main attractions are the two major parks - the Starved Rock State Park and the Matthiessen State Park. 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. Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December. Your email will not be provided to third parties. 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. 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. 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). Why you should visit: Orlando is known as a winter sun favorite so pack your sun cream and enjoy some time outdoors. Road Trip! The Best Travel Destinations Within Driving Distance of Chicago If you're here in winter, check out the National Gingerbread House Competition visitors can view entries into this big-money event. There are plenty of places to stop and a lot of parks and trails if you want to get out of the car. How to get there: Head east out of Chicago and join Interstate 90, then just keep going! Fennville has a few quirky local museums and things to see. The best thing about Madison, like many places in Wisconsin, is the food. Westin St. Maarten Dawn Beach Resort & Spa is located on one of the island's best beaches, and offers a variety of family-friendly amenities. You can also delve into the natural wilderness of Pisgah and Nantahala National Forests where you'll find more hiking opportunities, mountain biking routes, and the North Carolina Arboretum. The cheapest month to fly from Chicago is January. 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. Road Trip From Chicago To Washington DC - LazyTrips Take I-290 W from Chicago's downtown, which leads you out onto I-88. Best Weekend Getaways From Chicago | Cond Nast Traveler 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. 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. 14 most adorable direct flights from Chicago - Time Out Chicago 17 hours 30 minutes from Chicago (1,130 miles). The cheese fondue is right up there on our list of the best foods in the world! 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. 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. Our travel tips: Timed tickets are needed for some of Philadelphia's winter attractions, including Longwood Gardens and Dickens Village. 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. 8. Then head quickly back into the warmth of your hotel to warm up. 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. Denver is the gateway to Rocky Mountain National Park, as well as being a great place to head to in winter if you want to ski or snowboard on nearby slopes. Kentucky is only about seven hours from Chicago. 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. 'Peter Pan & Wendy' review: A real-live adventure this time from Disney The temperatures surpassed the 136-year-old . Motor City is the second largest city in the Midwest after Chicago and is worth making the drive for. Just after London, the road merges with ON-403, which will take you right into the center of Toronto. September and October are the best times to come to Cedarburg - the trees glow with their oranges and maroons and the locals celebrate Oktoberfest with special events, seasonal beers and great food. 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). And if you're missing that traditional winter vibe, visit Now Snowing in Celebration, where frosty views meet Florida sun including hourly snow flurries. Rockford lives up to its main nickname with plenty of outdoor spaces to explore - the Anderson Japanese Gardens, Klehm Botanic Garden and the Rock Cut State Park are all within the metropolitan area. Galleries, restaurants and local businesses come together to bring some warmth and cheer to the new year, with a legendary chilli cook-off, Soup-A-Thon and ice sculptures dotted around town. 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. 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. Stop at the Crane Orchards to sample one of their legendary pies as you make your way around! The festival also hosts many fun events. 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. 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. Here you can join in with the 9-day Winter Festival (late January). Or explore the wintery wilderness of Kishwauketoe Nature Conservancy - you can rent snowshoes if you don't have your own. 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. You must try the Glarner Stube restaurant in town. 2 hours 30 minutes from Chicago (147 miles). You can survey the options from atop the California Tower in Balboa Park. 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. 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. 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. Back in town, Denver has one of the largest Hispanic populations in the US, so the city's Museo de las Americas is well worth a visit, covering Hispanic culture and art. getty. How to get there: Follow I-90 east towards Cleveland, switching onto I-80 just before you reach the city. 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. Remember that Minneapolis can get cold, and even feel cool in the summer. 19 Awesome Road Trips from Chicago (with Timings) - VickyFlipFlopTravels Around 20 miles south of New Glarus and a little closer to Chicago is the city of Monroe. It's not all about the outdoors though. After Gainesville, join the Florida Turnpike which takes you the last stretch of the drive into Orlando. Leave time to explore. ETA: 10+ hours with couple of short breaks. The high temperatures that hit Chicago Thursday broke a record that stretched all the way back to 1887, according to the National Weather Service.