Jane Simon Ammeson

360 Chicago Observation Deck (photo by Nick Ulvieri)

Rising more than 1,000 feet over the Chicago’s Magnificent Mile, this spot provides panoramic vistas of skyscrapers, streets and vast blue of Lake Michigan. 

Absolutely Chicago Segway Tours in Chicago Illinois (photo courtesy of Absolutely Chicago Segway Tours)

The Ghosts and Gangsters tour offers a fun way to explore Chicago while connecting with its history.

Bottleworks Hotel in Indianapolis, Indiana (photo courtesy of Bottleworks District)

The former home of the world’s largest Coca-Cola bottling plant is now a downtown Indianapolis nightlife destination. 

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Chicago Architecture Foundation Center River Tour in Chicago, Illinois (photo by Barry Butler)

See and learn about some of the most famous buildings in Chicago, Illinois, from the water during this Chicago River cruise. 

Crystal Mountain in Thompsonville, Michigan (photo courtesy of Crystal Mountain)

Enjoy a wealth of outdoor adventures at this resort in Thompsonville, Michigan. Fall and winter offer plenty of opportunities to get outside. 

Boats on Lake Huron at Drummond Island on Lake Huron, Michigan (photo courtesy of Visit Drummond Island)

Make a couples getaway to this island in Lake Huron off the coast of Michigan's Upper Peninsula. Enjoy swimming, paddling and a wealth of other on-the-water activities.

Goats at Evergreen Lane Farm & Creamery in Fennville, Michigan (photo courtesy of Evergreen Lane Farm & Creamery)

Visit this 40-acre farm and cheese-making operation in Fennville, Michigan, where playful La Mancha goats graze and play. 

Kayaking is one of the experiences available at Goldberry Woods in Union Pier, Michigan (photo courtesy of destination)

This Union Pier, Michigan, spot not far from the trendy beach towns along Lake Michigan offers an oasis of forests, gardens and orchards on a curve of the Galien River.

Hermitage Farm in Goshen, Kentucky (photo courtesy of Oldham KY Farm Tours)

This former farm in Goshen, Kentucky, is now a food-and-drink destination that offers overnight stays. 

Family at Howe Caverns in Howes Cave, New York (photo courtesy of Visit Schoharie County)

Go underground in Howes Cave, New York, for an exploration of nature located 156 feet below the surface of Schoharie County.

Indiana Dunes National Park in Porter, Indiana (photo courtesy of National Park Service)

Explore the history of the region as well as the nature supported by the Hoosier State’s famous lakeside sand dunes in Porter, Indiana. 

Jesse James Riding Stables in Cave City, Kentucky (photo courtesy of destination)

Get a family-friendly taste of the outlaw life by riding horses on guided tours and exploring caverns in Cave City, Kentucky

Short ribs at Joseph Decius restaurant in Roanoke, Indiana (photo courtesy of Joseph Decius)

Enjoy elegant farm-to-table fine dining in Roanoke Indiana’s small-town setting.

Torture instruments at the Medieval Torture Museum in Chicago, Illinois (photo courtesy of Medieval Torture Museum)

This macabre museum in Chicago showcases more than 100 torture devices — 30% of which are original to their time, while the rest are replicas that give visitors an idea of their craft and use.

Bike riders in Midewin National Tallgrass Prairie in Wilmington, Illinois (photo courtesy of Illinois Office of Tourism)

Bison graze and grasses blow on a gentle breeze in Wilmington, Illinois, at this sprawling prairie steeped in history. 

People swimming in giant sprinkle pool at Museum Of Ice Cream in Chicago, Illinois (photo courtesy of Museum Of Ice Cream)

This attraction housed in Chicago, Illinois’ historic Tribune Tower offers 14 installations, including the chance to swim in a pool of giant sprinkles. 

Plate of Korean pork ribs at NAMI Modern Korean Steakhouse in Louisville, Kentucky (photo by Sara Babcock)

Dig into new takes on classic Korean dishes at this Louisville, Kentucky, spot from James Beard Award nominee and “Top Chef” alum Edward Lee. 

Ohio River Cabins in Derby And Cannelton, Indiana (photo courtesy of Perry County Visitors Bureau)

These cabins located along the Ohio River in Derby and Cannelton, Indiana, offer relaxing places to stay and play. 

Boat on Patoka Lake in Birdseye, Indiana (photo courtesy of Patoka Lake Marina)

Head to this lake in Birdseye, Indiana, for a stay aboard a fully equipped houseboat and other on-the-water recreation.  

Pizza City, USA Tours in Chicago, Illinois (Labriola Chicago pizza photo courtesy of Pizza City, USA Tours)

James Beard Award-winning journalist Steve Dolinsky’s food tours show Chicago has much more to offer than deep-dish pies. 

Shedd Aquarium in Chicago, Illinois (photo courtesy of Visit Hendricks County)

Explore marine life in Chicago, Illinois, at this 422,000-square-foot aquarium that is the third-largest attraction of its kind in the Western Hemisphere.

Smithtown Seafood At West Sixth Brewing in Lexington, Kentucky (photo courtesy of destination)

James Beard Award-nominated executive chef Ouita Michel’s Lexington, Kentucky, seafood spot is all about sourcing local ingredients.

The famous falls at Tahquamenon Falls State Park in Paradise, Michigan (photo courtesy of Upper Peninsula Travel & Recreation)

This Paradise, Michigan, park on the state’s Upper Peninsula is known for its famous root-beer-hued waterfall.

The Last Refuge in Louisville, Kentucky (photo courtesy of The Last Refuge)

Have a drink at the Louisville, Kentucky, restaurant and bar that showcases Bob Dylan’s whiskey brand in a beautifully appointed former church.

The Soho Hotel & Residences in Toronto, Ontario (photo courtesy of destination)

In addition to its proximity to Toronto’s mix of theaters, restaurants and shops, this luxury hotel is also a short walk away from the Lake Ontario shoreline. 

The Whitney in Detroit, Michigan (photo courtesy of Visit Detroit)

Get into the spirit of Halloween at this 52-room mansion in Detroit, Michigan. Completed in 1894 it now houses an award-winning restaurant. 

Box of pastries and exterior of Warda Patisserie in Detroit, Michigan (photo courtesy of Warda Patisserie)

This James Beard Award-winning destination in Detroit, Michigan, is where Warda Bouguettaya creates savories and sweets reflective of her background and travels. 

Baseball Fans at Wrigley Field in Chicago, Illinois (photo courtesy of choosechicago.com)

Visit the home of the Cubs in Chicago to take in the sights and sounds of one of the most famous sports venues in history.