Along the way you'll pass the cities of Madison, La Crosse and Sioux City, and you'll cross both the Mississippi and Missouri Rivers. Winter Getaways From Chicago | USA Today This leads you south to join I-76, which you'll then follow past Pittsburgh, all the way across Pennsylvania. St Louis, MO Driving time from Chicago: 4 hrs 30 min While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly. Back in town, tour the River Arts District on foot to meet artists at work in their studios. Images by Dr. Alan Lipkin/Shutterstock.com, Road Trip From Chicago To Mackinac Island, Road Trip From Chicago To Yellowstone National Park, 22. 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! 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. Roadtrips to 5/6 days from Chicago 8-9 hrs driving max Rising 462 feet above the sea, the carillon tower recently reopened to the public after 80 years in solitude. 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 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. 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. Here you can see works by some of the great European artists as well as a wide collection of American art. 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. Take a magical horse-drawn carriage ride, check out entries for the Gingerbread House competition, and enjoy endless festive lights. You can easily fill a weekend here with fun and varied runs. 14 most adorable direct flights from Chicago - Time Out Chicago As with everywhere in Wisconsin, the food and drink scene takes center stage. Here are several interesting options that make a great family road trip and all within easy driving distance of Chicago. 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. 25 Best Road Trips From Chicago - LazyTrips You won't need any previous experience or equipment, as your entrance to the track includes a lesson and all the equipment you'll need to enjoy your visit safely. 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. Lake Monroe is the state's largest man-made lake. Indiana Dunes, Indiana 1 hour from Chicago (50 miles) Why you should visit: Pennsylvania combines the kind of winter fun you might expect, like sledding and skating, with some unique winter traditions. Where to Stay. 1 hour 30 minutes from Chicago (88 miles). 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. It took 14 years to complete the huge memorial sculpture at Mount Rushmore. 1. LazyTrips is a trading name of Uncle Bob Media Ltd. Aaron of L.A. Photography/Shutterstock.com, Sidra Monreal Photography/Shutterstock.com, Road Trip From Chicago To Mackinac Island, Road Trip From Chicago To Yellowstone National Park. Within a short distance of the city you can ski, skate, snow tube and sled, sometimes with beautiful views across Lake Mendota. 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. And one of the three sections of the Hoosier National Forest is immediate to this area. 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. Best for: Family fun or a romantic rendezvous. 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 . 'Peter Pan & Wendy' review: A real-live adventure this time from Disney 25 Best Weekend Getaways from Chicago - VacationIdea 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. The capital of Wisconsin is often overlooked in favor of its bigger brother Milwaukee 80 miles east. Why you should visit: Orlando is known as a winter sun favorite so pack your sun cream and enjoy some time outdoors. Hot Springs (Arkansas) Distance: 650 miles. If you're feeling active, there are places where you can sled on the frozen sand dunes. Make sure you grab some food at the Root beer Stand. At Coastal Georgia Botanical Gardens, you can follow the beautiful light trail through the magical gardens, for example, or take a holiday trolley tour or boat trip to see the city decked out in festive finery while enjoying a wonderful warm cider. Beer and baseball are the two things the city is particularly known for. Getting to St Louis is easy - the I-55 will take you all the way to the Gateway City. Nicknamed the Forest City due to the area's verdant woods and rivers, Rockford is also known as the Screw Capital of the World. 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. 2 hours 30 minutes from Chicago (155 miles). The first week of December is particularly busy, but many travellers report that the crowds and prices calm down a little mid-month. The most accessible section of this shore extends from the Indiana line 175 miles north to Ludington. Several of the hotels in town have excellent in-house spas, so you can treat yourself to some relaxation time during your trip. 15 Best Winter Road Trips from Chicago - LazyTrips It was an early adopter of snowmaking technology in the 1950s. The city is in a prime spot with a lot of road trip options for you to escape to the surrounding destinations within 5 hrs drive. 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. One of the best places to visit in Illinois, this state park features 18 canyons and 13 miles of hiking trails to explore. After around 250 miles of driving you'll cross the Maumee River then turn off onto I-75 heading towards downtown Toledo. For a really exhilarating ride, fly right above the snow on one of the 9 ziplines. This Mom n pop classic fast food diner has been in Oglesby since 1955 and serves top notch root beer floats and burgers. 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). Whether you're looking for an active break or a peaceful boat trip, there are plenty of opportunities to get out onto the water. 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. 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. In the evenings from May to September there's also a 45-minute ranger talk which ends with the lighting ceremony. 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. If you're in Grand Rapids earlier in the season, you can enjoy some great skiing at Cannonsburg Ski Area. Otherwise you can find a selection of different cheese styles and types. 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. As Christmas gifts go, a whole city is one we wouldn't mind receiving! 10 Best Road Trips From Chicago - Trips To Discover Our highlights: The nation's capital is a fantastic place to visit during the holiday period. The local Fermentorium brewery has some 24 different beers on tap - not too shabby for a local place! 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. Drive, reach and enjoy the beautiful states around. Visit in early February when the Winter Carnival comes to town and you can see firework displays or catch a fun ride on one of the resort's snow groomers. Get into the festive spirit and enjoy the iconic holiday views of the city - if it feels familiar, it's probably because they've featured in so many films and TV shows over the years. 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. Our highlights: From Thanksgiving onwards, enjoy a Reveillon Dinner a local tradition which now sees restaurants across the city offering seasonal Creole-inspired food all through December. 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. Thousands of people in absolutely dazzling costumes parade through the city in a historic tradition. Any suggestions fellas? You can easily visit for a day or stay the night to see more of the local sights and museums. So if you are already in Chicago then you should explore these 12 best road trips from Chicago. Things to do on Kauai include exploring the Waimea Canyon, Kkee State Park, Na Pali Coast and the Kalalau Trail. There are a few museums and sights to see - the Grand Rapids Public Museum and the Art Museum are both worth going to. The lake freezes over right through the winter, so you can head out with a guide for a unique ice-fishing experience. High season is considered to be June and July. 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 can also snowshoe, tube or skate if you want a break from the slopes. You can't take your car with you to Mackinac - you'll have to park it at one of the designated ferry parking lots and make your way across. 5 hours 40 minutes from Chicago (350 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. 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. As you approach St Louis, you will see the first and main sight in the city - the huge 630-foot tall steel Gateway Arch. 506 miles east of Chicago: Upper - Kettle Creek State Park. 12 Best Road Trips From Chicago - TripHobo So if time allows on your trip, you might like to tour a brewery or two or try some of the locally produced beers. 605 S. Prospect St., Galena IL, 800-717-2317. For those who want to go on a longer road, trip, the options above may not quite cut it so here are some longer routes that you might like the sound of: By joining our email list, you give LazyTrips permission to use your email for sending you newsletters, emails and updates including for marketing purposes. Fridays at the Hollywood Beach Theatre feature free live jazz, blues and pop music at oceanfront cafes. Other activities include spending the day at Kalapaki or Po'ipu beaches, setting. Then, soon after crossing the Mississippi River, change onto I-55 and follow it south. 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. So, pack up your skis and look out for your skates - but don't worry if you're not the biggest fan of the slopes, since you'll also find great restaurants, beautiful views and stunning spas at these weekend destinations. 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. Places to visit about 9 hours from Chicago - Within Hours You might get spring, and then again, you might have winter still hanging on! Sundays have a free Jazz Brunch outdoor concert series along the scenic Riverwalk. 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. 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. Make sure you check out a few live music venues. From here, pick up I-76 and follow it straight down to Denver. 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.