One of the great things about Toledo is that although it's one of the largest cities in Ohio, visiting is relatively straightforward. When it's complete the statue of Crazy Horse will be taller than the presidents at Mount Rushmore. In Milwaukee, switch onto I-43 and continue north, before leaving the interstate just after Saukville. Chicago is a fantastic hub for history, architecture, gastronomy and sports. I-80 is a notoriously busy road, with heavy commercial traffic and few landmarks of interest. Make sure you visit the Heidelberg project - the outdoor art installation uses salvage materials to highlight the plight of Detroit and its ongoing period of change through loud modern sculpture. Our travel tips: This is a really popular ski area, and lift passes can sell out during the busiest periods. 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. The festival also hosts many fun events. It took 14 years to complete the huge memorial sculpture at Mount Rushmore. Harbor Country is one of the most popular getaway destinations for Chicagoans. Kentucky might only provide about a twenty-degree warm-up, but during the super cold times, those twenty degrees can feel like heaven. 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. 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. How to get there: Head east out of Chicago and join Interstate 90, then just keep going! The fastest way to get to Minneapolis from Chicago is to go the I-90 and I-94 route across Wisconsin. 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. 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 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. 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. Why you should visit: Seeing the famous falls cascading through the snowy ground is a truly magical experience and one that's different to any other trip you might take. Once you get to halfway point, you should spend a day or longer on Mackinac Island. 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. 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. 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. If you want to encourage a little less screen time during the summer break, take your family to explore the great outdoors in a Budget rental. 11 hours 10 minutes from Chicago (700 miles). It's the perfect way to enjoy the snowy conditions, and there are ski runs here to suit many different abilities. It features more than 100,000 lights and is the largest pipe organ in the world. 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. The first week of December is particularly busy, but many travellers report that the crowds and prices calm down a little mid-month. Then, follow WI-57 towards Plymouth, from where you'll pick up WI-67 to Elkhart Lake. Here you can see works by some of the great European artists as well as a wide collection of American art. Add in beautiful beaches all over, some big sand dunes, including the Indiana Dunes National Park and the pretty towns of Harbor Country. 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! But that's just the welcome mat to this SoCal haven. 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. 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). The cheese fondue is right up there on our list of the best foods in the world! You might consider day trips from Chicago to Milwaukee on the train. Millions of years of geologic changes are reflected at the Garden of the Gods in There are 4 large waterpark resorts (Kalahari, Great Wolf, Chula Vista and the Wilderness) and around 20 in total with more being constructed. 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. 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. 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. Then, follow the Christmas Parade, which makes its way through the city's streets and squares in early December. To make the most of the trip, take a couple of weeks and make a lot of stops along the way. 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. 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. Back in the city, entry to the world-class Toledo Museum of Art is free all year round. And one of the three sections of the Hoosier National Forest is immediate to this area. Constructed between 1906 and 1907, the Conservatory was conceived and designed by Chicago's West Park Commission's general superintendent and chief landscape architect, Jens . One is the Forever Curious Children's Museum - a non-profit organization created to spark a love for learning in kids of all ages. 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. Or if you're in town with romantic intentions, a stroll through the Diamond District might go down well. It's a popular place to visit, so book lift passes in advance if you know when you're travelling. Your email will not be provided to third parties. 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. Less than half of Toronto's residents were born in Canada, making for a varied and welcoming city that's the perfect place to head to on a road trip. How to get there: This is a really simple trip just follow I-90 all the way from Chicago. 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! Southern Illinois Distance: 6-hour drive Southern Illinois has a hilly landscape and a rural vibe. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights. MoneyGeek came up with this year's list by analyzing the FBI's crime statistics for 2021 (the most recent . How to get there: Follow I-90 west out of Chicago, passing Rockford and Madison. 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. Best road trips from Chicago Shutterstock 1. Also running from Thanksgiving right up to New Years Day is Celebration in the Oaks. Sundays have a free Jazz Brunch outdoor concert series along the scenic Riverwalk. Adrenaline junkies can ride ziplines in several places around Asheville, take a rafting trip or go canyoneering. You also don't have to book attractions weeks in advance, and you can find reasonably priced accommodation in the downtown area. 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. As far as Nashville I-55 runs parallel to the Mississippi before passing through Jackson. The two-lane road winds its way through the mountains, with plentiful overlooks and hiking trails to stop and explore. 506 miles east of Chicago: Upper - Kettle Creek State Park. (Disney Enterprises . 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. Given the city's mild winter climate, it's the perfect place to end the day with a romantic stroll. You must try the Glarner Stube restaurant in town. 8 hours 40 minutes from Chicago (530 miles). The interstate carries on across Nebraska and then splits just as you approach the northeast corner of Colorado. The locals didn't stop at naming the lake after the slightly better known one in Switzerland. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip. 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. Back in town you'll get beautiful winter views over icy Lake Michigan. The famous architect built the house in 1951 and it is interesting to see how far ahead of its time it is in terms of its design and accessibility - the look is incredibly modern despite some 70 years passing! At Louisville, change onto I-64 and follow it towards Lexington onto I-75 which takes you across into Tennessee. As well as sliding the high-speed downhill ice track, you can enjoy cross-country and downhill skiing, snowshoeing, and ice skating at the park. 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. Make sure you check out a few live music venues. Where's the warmest, sunniest place in Chicago during the winter months? The capital of Wisconsin is often overlooked in favor of its bigger brother Milwaukee 80 miles east. San Diego San Diego boasts 260 sunny days a year, miles of rugged beachside and barking seals. 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. 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!). 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. 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. 2643 Illinois Route 178. It was founded by a group of Swiss settlers from the Swiss canton of Glarus in 1845. PLAN YOUR TRIP: Visit Fodor's St. Maarten Guide Jo Ann. 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. Then join I-196 and follow it north along the lake shore until you reach Holland. Heading towards Lake Michigan, you will find the small harbor village of Saugatuck. New this winter, try curling. Bonus: These days you usually need to take a ferry across from Manhattan to Staten Island, but back in 1780 the entire harbour froze so hard that it was possible to walk all the way across the river. 5 hours 40 minutes from Chicago (350 miles). As well as Mardi Gras, New Orleans is also a vibrant city where you can enjoy live music, fabulous food and warm winter weather - perhaps the closest you can get to a trip overseas without needing a passport! 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 city is famous for Mardi Gras, which takes place in late February, but warm-up events actually start in January, so you can enjoy week after week of enjoyment. Why you should visit: As its name suggests, Granite Peak is a fabulous and long-established ski destination with some top-class runs and luxurious resort choices. Minneapolis straddles both sides of the Mississippi and has over a dozen lakes within it's city limits which makes for amazing scenery. 2 hours 30 minutes from Chicago (155 miles). 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. 2 hours 40 minutes from Chicago (145 miles). 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. So, sit back, relax, and learn all you need to know in planning a road . Nicknamed the Forest City due to the area's verdant woods and rivers, Rockford is also known as the Screw Capital of the World. 4 hours 30 minutes from Chicago (280 miles). 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. 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. 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. 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. If an authentic windmill and fields of tulips is not Dutch enough, there is an entire Dutch Village to go to. 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. The main attraction is a 21-mile loop around the lake with stunning forest scenery and great views of the water. Of course, there are two sides to every story, and a few miles from Mount Rushmore you can visit the Crazy Horse Memorial. RV campgrounds 500 miles from Chicago. 1 hour 30 minutes from Chicago (88 miles). The Indian Museum of North America is nearby too. Our travel tips: Equipment can be rented at this resort but arrive early on weekends or holidays as it's first come, first served. The fast ferries will take under 20 minutes to get you there. The high temperatures that hit Chicago Thursday broke a record that stretched all the way back to 1887, according to the National Weather Service. A Little History. 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. 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. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition. Best for: Family fun or a romantic rendezvous. For a more magical festive feel, head to Frederick Meijer Sculpture Gardens. Weekend Getaways from Chicago: Market Street Inn - 3 hours . Our travel tips: Check ahead for dates of candle-lit snowshoe trails across the city. 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. Our highlights: Granite Mountain is one of the oldest ski resorts in the United States, and it's been at the forefront of innovation in the skiing industry. 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. 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. Just after London, the road merges with ON-403, which will take you right into the center of Toronto. How to get there: Similar to the Grand Rapids trip, follow I-90 then I-94 east out of Chicago as far as St Joseph. The area is also home to a number of very decent wineries. 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. 3 hours 20 minutes from Chicago (190 miles). Denver also has a host of fabulous cultural attractions, so don't overlook the city itself on your way up to the mountains. 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. Muskegon Farmers Market operates indoors on Saturdays through the winter so you can warm up and stock up on some fabulous local produce. There's a real art to making Icewine and the conditions have to be just right to freeze the grapes for long enough on the vine. The rinks are super-festive in the run up to the holidays, and you can relax with a hot chocolate or a local craft beer afterwards. 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. Key stops include Minneapolis, Sacramento, Albuquerque, Las Vegas and Monterey, plus the Grand Canyon, Mojave National Preserve, Lake Tahoe and Yellowstone National Park. 809 Civic Center Dr., Niles; 847-972-2540 or kingspa.com. 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. 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. 17. 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! The small town of Oglesby, home to 3,600 people, is renowned for its natural beauty. Make sure you grab some food at the Root beer Stand. Choose from a lodge room, suite, 4-bed or 8-bed luxury cottage, ideal for multi-generation or multi-family groups. Things to do on Kauai include exploring the Waimea Canyon, Kkee State Park, Na Pali Coast and the Kalalau Trail. 13 hours 40 minutes from Chicago (925 miles). The village represents a historic view of Dutch settlements and you can even visit a wooden clog (shoe) making factory. Alternatively, if you'd prefer to just relax and unwind, maybe after a tour round the Christmas market or some time on the ice rink, head to the luxurious Aspira Spa to round off your trip. Chicago is a fantastic city, known for its stunning lakeside location, the Magnificent Mile, and its world-class museums and galleries. As well as being able to see the famous memorial in person, this is a great road trip that takes you from one side of the Great Plains to the other via some interesting and varied cities. Greater . If you are looking for cheap weekend getaways from Chicago, this is a good place to stay. 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. Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota. Hike along Michigan's Sleeping Bear Dunes National Seashore on your next weekend getaway from Chicago. 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. Wrap up warm and walk out towards Muskegon South Breakwater Lighthouse a really stunning sight or take a walk on the lake's frozen beaches. 17 hours 30 minutes from Chicago (1,130 miles). Why you should visit: This is a year-round resort, but with 140 inches of snow, it comes into its own during winter. 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. Top tips for finding a cheap flight out of Chicago Book at least 2 weeks before departure in order to get a below-average price. 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. The event runs in late Jan or early Feb, and hundreds of the city's restaurants showcase their best meals at reasonable prices - the perfect way to brighten up a long, cold winter. 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. Getting to St Louis is easy - the I-55 will take you all the way to the Gateway City. 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. 2 hours 20 minutes from Chicago (140 miles). 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! The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. The cheapest month to fly from Chicago is January. 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. The extensive and varied ski slopes here are great for a wide range of skiing abilities. Continue along the interstate then, after skirting the west side of Lake Pontchartrain, merge onto I-10 which takes you into the center of New Orleans. This leads you south to join I-76, which you'll then follow past Pittsburgh, all the way across Pennsylvania. 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. A few of the upcoming options on our road trip list are all due north in Wisconsin. 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. That way, current and future visitors will be guaranteed the same fabulous experience of NOLA's longstanding and unique traditions. 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. 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. By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. 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. The temperatures surpassed the 136-year-old . 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. 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 get a tour of the mansion and explore the vast grounds which include 620 feet of shoreline. If you've had about enough of cheese, you can go on an ATV ride around the trail network around Monroe. 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! How to get there: After heading east out of Chicago on I-90, turn south onto I-65 and continue through Indianapolis and Louisville. 4 hours 30 minutes from Chicago (300 miles). Seeing the falls in winter is a magical experience, with massive icicles and undulating snow drifts surrounding the famous vistas. If 21 miles seems a little much, focus in on the 2-mile stretch on the West End. If you'd like to take a little shopping excursion, Nashville (IN) has a great many galleries and artisan shops. The 830-mile road trip from Chicago to Washington DC will take you around 14 hours to drive non-stop. How to get there: Follow I-90/I-94 north out of Chicago, then continue north on I-94 when the interstate divides. Then, join I-80 and follow it around the south of Cleveland before switching onto I-76 and continuing southeast past Pittsburgh. If you're able to visit mid-week, you'll probably find the slopes are quieter. Next, pick up I-40 which winds through a section of the Appalachian Mountains on its way to your destination, Asheville. Ride down the Kalamazoo River on a paddle steamer, explore the lakeshore and river in a kayak, or charter a yacht. From jazz to soul, St Louis has been one of the most prominent musical cities in the US - Tina Turner and Scott Joplin started their careers here among others. Highlights include the cities of Indianapolis, Dayton and Columbus; as well as Wayne National Forest, Seneca Rocks, Shenandah National Park and Monongahela National Forest. Then, shortly after crossing the Wisconsin River, turn onto I-39 and follow it north to Granite Peak Ski Area. 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. Expect congestion on the Blue Ridge Parkway, especially if you visit at weekends. Went to New York (which was fun) so that is covered. 12 hours 40 minutes from Chicago (800 miles). After Grand Rapids, turn onto Route 131 and continue north past Big Rapids and Cadillac, until you reach Boyne Mountain. 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. 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. 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. But did you know that every single participant has to wear one? 1. They don't run every day, but when they do they're really magical. Drive time: 2 hours from downtown. Why you should visit: With festive lights, winter markets, a good chance of snow, and plenty of big city attractions, Toronto is a picture-perfect winter city trip.