14 unexpected great vacations from Chicago

Chicago offers awesome direct flights to destinations that are the perfect combination of cute, quick and cheap
Photograph: Zack/Flickr
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Some of the most intriguing direct flights out of Chicago's O'Hare International Airport are replete with mountains, water and swathes of green space straight out of a museum painting. If you're bored with driving through the best day trips from Chicago or aren't up for a scenic train ride or somewhere as steamy as Puerto Rico, check out these quick, fun vacations. These travel desinations have scenery up the wazoo and make great weekend jaunts for busybodies with only days to spare or those of us with an entire week's worth of vacation to burn.

Prices and flight times reflect information found at the time of publication. 

RECOMMENDED: More weekend getaways from Chicago

 

Photograph: Wikimedia Commons

Anchorage, AK

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.

Photograph: Smart Destinations/Flickr

Asheville, NC

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.

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Photograph: Pixabay

Aspen, CO

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.

Photograph: Amy Guth/Flickr

Bozeman, MT

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!

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Photograph: Jeff Gunn/Flickr

Chattanooga, TN

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?

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Photograph: Wikimedia Commons

Columbia, SC

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.

Photograph: Randen Pederson/Flickr

Duluth, MN

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.

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Photograph: Matthew Straubmuller/Flickr

Fort Myers, FL

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.

Photograph: David Ohmer/Flickr

Lexington, KY

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.

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Photograph: Rachel Kramer

Marquette, MI

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.

Photograph: Wikimedia Commons

Portland, ME

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.

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Photograph: Liz West/Flickr

Providence, RI

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.

Photograph: Jeff Gunn/Flickr

Savannah, GA

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.

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