14 unexpected great vacations from Chicago

Flight $$$: $500

Time in the air: 7 hours

Best attractions: Tour the Cook Inlet by boat or try paddling through the gorgeous Eklutna Lake. There are also many, many trails and a wonderful lookout over the city at Flattop Mountain.

Flight $$$: $300

Time in the air: 2 hours

Best attractions: Tour the grounds and gardens of the Biltmore Estate, then drink your way through a truly staggering amount of quality local breweries like Hi-Wire Brewing and Green Man.

Flight $$$: $550

Time in the air: 3 hours

Best attractions: Skiing, duh. Also try checking out the famous Maroon Bells. And remember, folks, marijuana is legal if you so wish to "enhance" your journey.

Flight $$$: $500

Time in the air: 3 hours

Best attractions: The Museum of the Rockies, which has the largest collection of dinosaur bones in the U.S. Also, just a 90-minute drive from Yellowstone!

Flight $$$: $375

Time in the air: 2 hours

Best attractions: Gobble up the Ben & Jerry’s Ice Cream factory tour. There’s also a handful of seriously great breweries like Magic Hat Brewing Co. and Queen City Brewery. Do yourself a favor and get out to the mountains as well—it's like nowhere else in the States.

Flight cost: $250

Time in the air: 2 hours

Best attractions: The breathtaking views from high above at Lookout Mountain or deep underground winding through the Raccoon Mountain Caverns. Need we say more?

Flight $$$: $300

Time in the air: 2 hours

Best attractions: Canoe through Cedar Creek in Congaree National Park, which although it looks like a swamp, actually isn’t. Plan a trip around late winter rain so the forest is flooded.

Flight $$$: $225

Time in the air: 1.5 hours

Best attractions: Explore the downtown area and be sure to find the William A. Irvin, a decommissioned iron ore and coal freighter parked along the shore of Lake Superior, and travel belowdecks, walking the gangways and picking up a thing or two about the area's history along the way.

Flight $$$: $125

Time in the air: 3 hours

Best attractions: Rent a few mopeds and buzz your way along Fort Myers Beach and Estero Island, stopping at all the cute cafes and beaches as you go. Seriously, you don't even have to leave this thin island of beach for your entire stay. The nice weather, a few cheap cocktails and a pair of sunglasses are all you need.

Flight $$$: $225

Time in the air: 1 hour

Best attractions: Billed the “horse capital of the world,” it would be a shame to not pay a visit to the legendary horse tracks at Keeneland to bet on a race or two, or check out the positively huge Kentucky Horse Park.

Flight $$$: $325

Time in the air: 1.5 hours

Best attractions: Walking and shopping the incredibly picturesque downtown along Lake Superior’s shore. A bountiful farmers' market sells fresh produce, the Lower Harbor Ore Dock majestically extends into the water and the view from Sugarloaf Mountain is nothing to scoff at.

Flight $$$: $400

Time in the air: 2 hours

Best attractions: We’re not ashamed to say, this is the better Portland. Take one of the plentiful boat tours and explore the islands in Casco Bay or go out on your own and hit the trails along the seaboard. Also, have yourself a lobster roll.

Flight $$$: $225

Time in the air: 2 hours

Best attractions: The quaint digs. This East Coast city replete with classic American architecture and incredible public institutions and parks is often unfairly written off as a college town, when really it's a great escape from the city with great food and drink.

Flight $$$: $300

Time in the air: 2 hours

Best attractions: Strolling through Bonaventure Cemetery and the squares. Savannah is the first city in the U.S. where the grid system was established, and many of the city’s intersections are squares.