15 days in Midwest Itinerary

15 days in Midwest Itinerary

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Route & dates

15 days in Midwest Itinerary

Start: Atlanta
Fly + Drive:  4​h 45​min
1
New Haven
— 1 night
Drive:  3​h 45​min
2
Weston
— 3 nights
Drive:  2​h 45​min
3
Omaha
— 2 nights
Fly:  4​h 15​min
4
Chicago
— 5 nights
Fly:  3​h 15​min
5
Cleveland
— 3 nights
Fly:  3​h 45​min
End: Atlanta

1
night
New Haven

New Haven ©
New Haven is a city in Franklin County, Missouri, United States. On the 21st (Sat), learn about winemaking at Robller Vineyard and then brush up on your knowledge of spirits at Pinckney Bend Distillery. Here are some ideas for day two: learn about winemaking at Bommarito Estate Almond Tree Winery, then do a tasting at Wenwood Farm Winery, and then do a tasting at White Mule Winery.

To see ratings, reviews, maps, and other tourist information, use the New Haven journey planner.

Atlanta to New Haven is an approximately 5-hour combination of flight and car. You can also drive. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. Traveling from Atlanta in December, expect New Haven to be a bit cooler, temps between 44°F and 27°F. Finish your sightseeing early on the 22nd (Sun) so you can travel to Weston.

Things to do in New Haven

Wineries Breweries & Distilleries

Side Trips

White Mule Winery, Wenwood Farm Winery
Highlights from your plan
Pinckney Bend Distillery ©
Pinckney Bend Distillery
Wenwood Farm Winery ©
Wenwood Farm Winery
Bommarito Estate Almond Tree Winery ©

3
nights
Weston

Weston ©
Weston is a city in Platte County, Missouri, United States. Change things up with these side-trips from Weston: Holy-Field Vineyard & Winery (in Basehor), Missouri Theatre (in Saint Joseph) and Bluejacket Crossing Vineyard and Winery (in Eudora). Next up on the itinerary: sample the fine beverages at Holladay Distillery, learn about winemaking at Riverwood Winery, and tee off at Firekeeper Golf Course.

For photos, other places to visit, traveler tips, and tourist information, you can read our Weston day trip site .

Getting from New Haven to Weston by car takes about 4 hours. Other options: do a combination of car and flight. In December, plan for daily highs up to 42°F, and evening lows to 24°F. Wrap up your sightseeing on the 25th (Wed) early enough to travel to Omaha.

Things to do in Weston

Wineries Historic Sites Nightlife

Side Trips

Jowler Creek Winery, Ladoga Ridge Winery, Bluejacket Crossing Vineyard and Winery, Firekeeper Golf Course, Riverwood Winery
Highlights from your plan
Holladay Distillery ©
Holladay Distillery
Pirtle Winery ©
Pirtle Winery
Jowler Creek Winery ©
Jowler Creek Winery

2
nights
Omaha

Omaha ©
A major transportation hub, Omaha was once considered little more than a stopping point on a pioneer's journey west.
Start off your visit on the 26th (Thu): enjoy some music at Henry Doorly Zoo, try your luck at Horseshoe Council Bluffs, and then do a tasting at Bodega Victoriana Winery. Here are some ideas for day two: do a tasting at Glacial Till Vineyard and Winery, then sample the tasty concoctions at Nebraska Brewing Company, and then get a taste of the local shopping with Old Market.

To find ratings, where to stay, traveler tips, and tourist information, refer to the Omaha day trip app .

You can drive from Weston to Omaha in 3 hours. Expect a bit cooler weather when traveling from Weston in December: highs in Omaha hover around 37°F, while lows dip to 20°F. Finish your sightseeing early on the 27th (Fri) so you can travel to Chicago.

Things to do in Omaha

Wineries Nightlife Zoos & Aquariums

Side Trips

Nebraska Brewing Company, Glacial Till Vineyard and Winery, Horseshoe Council Bluffs, Bodega Victoriana Winery
Highlights from your plan
Bodega Victoriana Winery ©
Bodega Victoriana Winery
Horseshoe Council Bluffs ©
Horseshoe Council Bluffs
Henry Doorly Zoo ©
Henry Doorly Zoo

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Explore the numerous day-trip ideas around Chicago: Spas (in Lake Geneva) and Prairie States Winery (in Genoa). There's still lots to do: try your luck at Horseshoe Hammond, enjoy breathtaking views from Skydeck Chicago - Willis Tower, engage your brain at Museum of Science and Industry, and admire the striking features of 360 Chicago Observation Deck.

For other places to visit, photos, maps, and tourist information, refer to the Chicago trip planner .

Traveling by flight from Omaha to Chicago takes 4.5 hours. Alternatively, you can do a combination of car and flight; or drive. Plan for somewhat warmer nights when traveling from Omaha in December since evenings lows in Chicago dip to 26°F. Wrap up your sightseeing on the 1st (Wed) to allow time to travel to Cleveland.

Things to do in Chicago

Museums Childrens Museums Parks

Side Trips

Horseshoe Hammond, Block Museum of Art, Spas, Prairie States Winery
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Horseshoe Hammond ©
Horseshoe Hammond
The Magnificent Mile ©
The Magnificent Mile

3
nights
Cleveland

Cleveland ©
A culturally diverse city situated on the shores of Lake Erie, Cleveland boasts many places to visit, such as world-class museums, popular amusement parks, and sprawling recreational areas.
You'll find plenty of places to visit near Cleveland: Hard Rock Rocksino Northfield Park (in Northfield), Hundley Cellars (in Geneva) and Barrel Run Crossing Winery (in Rootstown). There's lots more to do: try your luck at JACK Cleveland Casino, examine the collection at Rock & Roll Hall of Fame, admire the masterpieces at The Cleveland Museum of Art, and wander the streets of University Circle.

For other places to visit, traveler tips, maps, and tourist information, read Cleveland trip planner .

You can fly from Chicago to Cleveland in 3.5 hours. Other options are to do a combination of subway, bus, and flight; or drive. The time zone difference when traveling from Chicago to Cleveland is 1 hour. Expect a daytime high around 34°F in January, and nighttime lows around 22°F. Finish your sightseeing early on the 4th (Sat) to allow enough time to travel back home.

Things to do in Cleveland

Fun & Games Casinos Museums

Side Trips

Barrel Run Crossing Winery, Hard Rock Rocksino Northfield Park, Hundley Cellars, Bay Lanes Bowling
Highlights from your plan
JACK Cleveland Casino ©
JACK Cleveland Casino
Hundley Cellars ©
Hundley Cellars
Barrel Run Crossing Winery ©
Barrel Run Crossing Winery

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