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Thursday, September 21, 2023

Long Weekend Trips From Chicago

Why Take A Road Trip From Chicago

Chicago Travel Vlog: How I spent my weekend in Chicago 2021

The state of Illinois is bordered by four other states. Each one has something great to offer in the way of landscape, atmosphere, and culture. By visiting some of the surrounding areas youll have a much better understanding of the mid-west. As much as we love Chicago, we think its imperative that visitors take at least one road trip from Chicago!

Whether you want to escape the city for a day or plan a romantic weekend getaway from Chicago were here to help. Weve compiled a list of the best places to visit near Chicago to help you narrow down your options. From lakeside retreats to nature parks to lively cities theres a place on the list for everyone.

Most of the spots on this list deserve at least a day to visit, and some require more time. Youll want to save an entire weekend for the trip. If youre able to travel by car youll have much more freedom to explore. However, most of these places to visit near Chicago can be reached by train or bus as well.

Are you ready to delve into our list of the best road trips from Chicago? Lets go!

Indiana Dunes National Lakeshore

Indiana Dunes National Lakeshore provides visitors with a 15-mile stretch of beach along Lake Michigans southern shore thats perfect for a beach day getaway. Fifty miles of diverse trails weave along the lakeshore where visitors can hike, bike, ride on horseback, snowshoe, cross-country ski, or bird watch.

Besides beaches, highlights include interpretive programs, ranger-led walking tours, the childrens outdoor Nature Play Zone at the Paul H. Douglas Center, four historical buildings from a 19th century homestead, and a 3500-square-foot modern pavilion. Every day trip should include a hike up West Beachs Succession Trail for an epic view of the Chicago skyline.

1100 N. Mineral Springs Road, Porter, IN, Phone: 219-395-1882

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Boyne Mountain Resort Boyne Falls Michigan

Distance from Chicago: 346 miles, 5-hour driveSki slopes dont usually come to mind when folks think of winter in the midwest, but Boyne Mountain Resort will have you mistaking northwestern Michigan for Park City, Utah . Regardless, this snowy palace boasts 415 skiable acres, 60 downhill runs, seven terrain parks, and ski lifts soaring as high as 500 feet. There are plenty of options for all skill levels here, and if youre just starting out , you can glide down the bunny slope to your heart’s content without dropping any extra cash. Sister resort Boyne Highlands sports some more advanced slopes for those wanting a steeper challenge, and if you haven’t had enough winter adventuring, head over to Gaylord State Forest, which boasts trails upon trails of natural beauty.

Between runs, check out other draws like ziplining, tubing, cross-country skiing, ice skating, fat tire snow biking, SNO-GO biking, and, if that wasnt enough, a full-scale indoor waterpark for those who just cant kiss summer goodbye. Before tucking into bed inside your villa or lodge, unwind at the onsite spa, packed with an array of body treatments, like facials, massages, and BEMER therapy. Because, hey, youre worth it.

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The Knickerbocker On The Lake

The Knickerbocker on the Lake is a restored boutique hotel located in the heart of downtown Milwaukee. The property is within walking distance of a number of restaurants, museums, theaters, and transportation options. The 160 guest rooms and suites are decorated with period-influenced furniture and modern conveniences such as fully equipped kitchenettes and Wi-Fi. Some suites have views of the picturesque Lake Michigan shoreline.

The full service Knick Salon and Spa offes invigorating treatments, while the Juneau Room is a spacious area ideal for hosting special events. Guests can work out at the 24-hour fitness center, request custom tailoring and valet dry cleaning.The Knick Restaurant offers upscale dining, with a menu that provides something to suit every gourmand. Weekend guests should not miss the bountiful Sunday brunche. If you are looking for cheap weekend getaways, rooms start at just $119 per night.

1028 E Juneau Ave, Milwaukee, WI 53202

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Abraham Lincoln Presidential Library And Museum

Long Weekend in Chicago: The windy city

The Abraham Lincoln Presidential Library and Museum gives visitors from across the globe a chance to learn about The Great American Story that is Abraham Lincoln. The museum offers a wide range of interactive learning activities and full-immersion exhibits. Civil War artifacts, precious documents, traveling exhibits, and walking tours are a few of the highlights.

Annual events such as art contests and museum scavenger hunts provide unique ways of absorbing both this era and President Lincolns story. The library features manuscripts, newspapers on microfilm, bibliographies, and other printed materials for an in-depth study of one of the United States most influential presidents.

112 N. Sixth Street, Springfield, IL, Phone: 217-557-6250

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Road Trips From Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

Whether youre taking the car out for an hour-long spin or youre willing to buckle down for a few hours, you wont be disappointed by the scenery along your journey or the fantastic destinations ahead.

St Thomas Us Virgin Islands

Travel time: Four hours from New York under three from Miami. You can find flights for well under $300 depending on where youre coming from, particularly in the off-season — hurricane season is wrapping by late October, too, making this an ideal winter getaway.

Why youll love it: Are we cheating once more with another destination thats not technically international? Yes. Why? Look at that photo, dummy. In the two years since the back-to-back blows of hurricanes Maria and Irma, US Virgin Islanders have pulled off an extraordinary recovery. Restaurants, hotels, shops, beaches of course — everything you could want or need is up and running. Its been remade better stronger. And dont think of St. Thomas as just a passenger dumping-ground for cruise ships, because the proper way to explore it is definitely under your own power.

Start by taking a walking tour around St. Thomas gorgeous historic downtown, during which you can ask for personalized recommendations for where you should head next. Journey over to St. Croix for the pristine beaches and maybe a turtle or two. Snorkel through the light, light blue water, which will be warm no matter when you go. Try as many varieties of mangoes as you can get your hands on — Kastalia Medrano

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Walk Down The Magnificent Mile

Start the day with a trip down the Magnificent Mile. This is a section of Michigan Avenue that is the retail center of Chicago. The street is lined on both sides with tons and tons of flagship stores, boutiques, and shopping malls.

Along the Magnificent Mile, in addition to all of the premier shopping, there are a few awesome sights youll see during this part of your Chicago weekend getaway.

The Wrigley Building is an awesome structure located right where Michigan Avenue meets the Chicago River. The Tribune Tower and the Chicago Water Tower are also wonderful landmarks along this stretch.

Stroll Through Some Parks


Chicago has a lot of green space and public park land and a lot of it is close to the lake shore.

If you’re looking for a great place for a walk, head to Millennium Park and Grant Park. Here you’ll find the famous Cloud Gate sculpture , the Jay Pritzker Pavilion, Buckingham Fountain, and so much more.

If you have your walking shoes on, you can actually walk all the way from Millennium Park through Grant Park to Museum Campus.

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Weekend Getaways Near Chicago: Bishops Hall

Bishops Hall was built in 1916 and features Georgian revival style architecture and sits in historic Oak Park. All rooms are decorated in the Georgian style. There are three guest rooms to choose from, each of which is unique and features a private bath and queen-sized four-poster bed. Amenities vary by room but some have balconies, separate dressing rooms, marble baths, fireplaces, multiple seating areas, claw foot tubs, steam rooms, and European hand showers. Every room has toiletries, hair dryers, and robes along with chocolates and fresh flowers.

Guests can enjoy the garden and terrace. The morning begins with a full breakfast available in one of several rooms, giving guests the option of being social or enjoying a private meal. You can eat breakfast on the balcony or terrace in nice weather. Rooms start at $175 per night. Keep reading for more resorts near me.

605 Iowa St., Oak Park IL, 708-383-7774

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Head To Wrigley Field & Wrigleyville

You cant visit the North Side of Chicago and not see Wrigley Field. As one of the most famous baseball stadiums in existence, and the home of the Chicago Cubs, this is a must-see stadium, especially for sports fans.

Wrigley Field is located right in the heart of Wrigleyville on the North Side. Surrounded by residential areas and a huge bar and restaurant scene, this area is a magnet for good times, especially when the hometown Cubs are lacing up their cleats for a game.

If you are fortunate enough to be in Chicago while the Cubs are playing, head to Wrigley just for the experience of people watching and cheering on the hometown team. If youd like, you could even try and buy some tickets, and usually, you can get a good deal on seats if you are okay purchasing them after the game is already in the 2nd or 3rd inning.

Wrigleyville, the neighborhood surrounding Wrigley Field, is an excellent place to hang out, have a drink, and hop around a few of the local establishments. Each of them has a great atmosphere, delicious, food, and of course a wide array of beers on tap.

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Take A Loop Around Lake Michigan And Visit The Upper Peninsula

Picture a precious log cabin, almost dollhouse-like in its proportions. A campfire sits outside, with a pile of wood on the small porch, next to a comfy wicker love seat. Inside, a little wood stove and snowshoes are tempting draws for a return visit come winter, when guests can read the Nordic literature at the little wood table, pages lit by the cabins twinkling string lights.

This was home base for a trip to Michigans Upper Peninsula, where kayaking tours of Pictured Rocks, hiking through chipmunk-populated forests, and starry nights are a welcome respite. And communing with nature stunning scenery, air fresh and fragrant, and birch trees as far as the eye can see is a deeply restorative cure to the COVID-19 woes.

Weekend Getaways From Chicago: The Abbey Resort

Travel Guide: A Couples

The Abbey Resort is a full service getaway on 90 scenic acres near the Fontana harbor, offering 334 deluxe guestrooms, 13 spacious suites and 13 villas. The 35,000-square-foot Avani Spa offers massages, facials, wraps, aromatherapy and saunas on your weekend trip.

Resort facilities include a fitness center, aerobic studio, indoor and outdoor swimming pools, a disk golf course, and a games arcade for kids. Dining options range from casual cafes to gourmet restaurants, including 240 West, Café Latte, the Waterfront Restaurant Bar & Grill, Bar West and Porto. Weekend activities include watersports, bike rides, golf, walking and jogging around the lake. If you are looking for affordable resorts near Chicago, rooms start at $89 per night.

269 Fontana Blvd, Fontana-On-Geneva Lake, WI 53125

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Cuyahoga Valley National Park

  • Virginia Kendall Ledges
  • Brandywine Falls

Did you know there was a beautiful National Park in Ohio? We recently discovered Cuyahoga Valley National Park and loved it. The national park is located between Cleveland and Akron Ohio and is perfect for weekend getaways from Chicago.

It is one of the newest National Parks in the US and was created to save the history of the lock system along the Cuyahoga River.

Some highlights of the park are an easy family hike to the scenic Brandywine Falls. Visiting two great visitor centers that explain the history of how the lock systems worked in the 1800s and the people who lived in the area.

But the biggest highlight for us was an amazing hike through moss-covered boulders that make you feel like your in another world. Your kids will love climbing all over these beautiful rocks and exploring the park.

Cuyahoga Valley National Park is different than most because you will find towns mixed in throughout the park system rather than being in a more remote area.

The bonus is you have easy access to lots of hotels and lodging in Akron and Cleveland. Plus your near restaurants and shops. This would be a great day trip too if youre passing through the area.

Learn more about all there is to do and tips for your visit in Best Guide to Cuyahoga Valley National Park and Brandywine Falls.

Where to Stay in Akronand Cleveland

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