14 days in Atlanta, Lexington & Chicago Itinerary

14 days in Atlanta, Lexington & Chicago Itinerary

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Route & dates

14 days in Atlanta, Lexington & Chicago Itinerary

New York City
bus + Fly:  4​h 30​min
Atlanta
— 4 nights
Fly:  2​h 45​min
Lexington
— 2 nights
Fly:  3​h 15​min
Chicago
— 6 nights
Fly + bus:  4​h 45​min
New York City

4
days
Atlanta

Atlanta
Georgia’s largest city and capital, Atlanta is a thriving metropolis anchored by its southern roots.
Do some cultural sightseeing at Ocmulgee National Monument and Booth Western Art Museum. You'll explore and learn at Tellus Science Museum and Allman Brothers Band Museum. Explore Atlanta's surroundings by going to Chateau Meichtry Family Vineyard and Winery (in Talking Rock), Stone Mountain Park (in Stone Mountain) and Burt's Farm (in Dawsonville). There's more to do: stroll through Centennial Olympic Park and wander the streets of Buckhead.

To see photos, reviews, other places to visit, and more tourist information, read our Atlanta online itinerary builder .

New York City to Atlanta is an approximately 4.5-hour combination of bus and flight. You can also do a combination of train and flight; or drive. Expect somewhat warmer weather when traveling from New York City in December: highs in Atlanta hover around 60°F, while lows dip to 43°F. Finish up your sightseeing early on the 27th (Wed) so you can travel to Lexington.

Things to do in Atlanta

Museums Outdoors Parks

Side Trips

Macon, Cartersville, Burt's Farm, Stone Mountain Park, Chateau Meichtry Family Vineyard and Winery
Highlights from your plan
Ocmulgee National Monument
Ocmulgee National Monument
Tellus Science Museum
Tellus Science Museum
Booth Western Art Museum
Booth Western Art Museum

2
days
Lexington

Lexington
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
On the 27th (Wed), contemplate the long history of Old Fort Harrod State Park, then brush up on your knowledge of spirits at Limestone Branch Distillery, and then play a few rounds at My Old Kentucky Home. Here are some ideas for day two: take in the exciting artwork at Berea Arts Council, then take in the exciting artwork at Kentucky Artisan Center at Berea, and then identify plant and animal life at Raven Run Nature Sanctuary.

To see traveler tips, reviews, where to stay, and tourist information, read our Lexington planning app .

Traveling by flight from Atlanta to Lexington takes 3 hours. Alternatively, you can drive; or take a bus. Prepare for slightly colder weather when traveling from Atlanta in December: high temperatures in Lexington hover around 49°F and lows are around 34°F. Wrap up your sightseeing by early afternoon on the 29th (Fri) to allow enough time to travel to Chicago.

Things to do in Lexington

Historic Sites Parks Wildlife

Side Trips

Berea, Limestone Branch Distillery, Old Fort Harrod State Park, My Old Kentucky Home
Highlights from your plan
My Old Kentucky Home
My Old Kentucky Home
Old Fort Harrod State Park ©
Old Fort Harrod State Park
Kentucky Artisan Center at Berea ©
Kentucky Artisan Center at Berea

6
days
Chicago

Chicago
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Millennium Park and Chicago Riverwalk will appeal to history buffs. Get a sense of the local culture at The Art Institute of Chicago and The Field Museum. You'll find plenty of places to visit near Chicago: Silver Beach County Park (in Saint Joseph), St. Julian Winery-Union Pier (in Union Pier) and Utica (August Hill Winery Tasting Room & Starved Rock State Park). There's still lots to do: get curious at Museum of Science and Industry, Chicago, view the masterpieces at Chicago Cultural Center, pause for some photo ops at Cloud Gate, and don't miss a visit to The Magnificent Mile.

To find other places to visit, ratings, traveler tips, and tourist information, read Chicago online road trip planner .

Fly from Lexington to Chicago in 3.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. Prepare for a bit cooler weather when traveling from Lexington in December: high temperatures in Chicago hover around 39°F and lows are around 28°F. Wrap up your sightseeing on the 4th (Thu) to allow time to travel back home.

Things to do in Chicago

Parks Museums Outdoors

Side Trips

Utica, Silver Beach County Park, St. Julian Winery-Union Pier, Lake Michigan
Highlights from your plan
Starved Rock State Park
Starved Rock State Park
The Art Institute of Chicago ©
The Art Institute of Chicago
Silver Beach County Park ©
Silver Beach County Park

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