15 days in Midwest Itinerary

15 days in Midwest Itinerary

Created using Inspirock Midwest trip builder

Plan created by another user. Make it yours
1
New Haven
— 1 night
2
Weston
— 3 nights
3
Omaha
— 2 nights
4
Chicago
— 5 nights
5
Cleveland
— 3 nights

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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, learn about winemaking at Wenwood Farm Winery, and then learn about winemaking at White Mule Winery.

For traveler tips, where to stay, and other tourist information, you can read our New Haven visit planner.

Atlanta to New Haven is an approximately 5-hour combination of flight and car. You can also drive. Due to the time zone difference, you'll gain 1 hour traveling from Atlanta to New Haven. In December, New Haven is a bit cooler than Atlanta - with highs of 44°F and lows of 27°F. Wrap up your sightseeing on the 22nd (Sun) to allow time to travel to Weston.

Things to do in New Haven

Wineries · Breweries & Distilleries

Side Trips

Highlights from your plan
Pinckney Bend Distillery ©
Pinckney Bend Distillery
Wenwood Farm Winery ©
Wenwood Farm Winery
Robller Vineyard ©
Robller Vineyard

3
nights
Weston

Weston ©
Weston is a city in Platte County, Missouri, United States. Explore the numerous day-trip ideas around Weston: Holy-Field Vineyard & Winery (in Basehor), Bluejacket Crossing Vineyard and Winery (in Eudora) and Missouri Theatre (in Saint Joseph). The adventure continues: learn about winemaking at Pirtle Winery, play a few rounds at Firekeeper Golf Course, and sample the fine beverages at Holladay Distillery.

To see traveler tips, other places to visit, maps, and tourist information, go to the Weston day trip app.

You can drive from New Haven to Weston in 4 hours. Another option is to do a combination of car and flight. December in Weston sees daily highs of 42°F and lows of 24°F at night. Finish your sightseeing early on the 25th (Wed) so you can travel to Omaha.

Things to do in Weston

Wineries · Golf · Outdoors · Nightlife

Side Trips

Highlights from your plan
Holladay Distillery ©
Holladay Distillery
Pirtle Winery ©
Pirtle Winery
Jowler Creek Winery ©
Jowler Creek Winery

2
nights
Omaha

Omaha ©

Gateway to the West

A major transportation hub, Omaha was once considered little more than a stopping point on a pioneer's journey west.
Kick off your visit on the 26th (Thu): enjoy some music at Henry Doorly Zoo, try to win big at Horseshoe Council Bluffs, and then do a tasting at Bodega Victoriana Winery. On the 27th (Fri), you'll have a packed day of sightseeing: learn about winemaking at Glacial Till Vineyard and Winery, sample the tasty concoctions at Nebraska Brewing Company, and then get a taste of the local shopping with Old Market.

To find other places to visit, traveler tips, photos, and tourist information, refer to the Omaha holiday builder website.

Traveling by car from Weston to Omaha takes 3 hours. When traveling from Weston in December, plan for a bit cooler days and about the same nights in Omaha: temperatures range from 37°F by day to 20°F at night. Wrap up your sightseeing on the 27th (Fri) early enough to travel to Chicago.

Things to do in Omaha

Wineries · Neighborhoods · Casinos · Zoos & Aquariums

Side Trips

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 ©

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll find plenty of places to visit near Chicago: Spas (in Lake Geneva) and Prairie States Winery (in Genoa). And it doesn't end there: try to win big at Horseshoe Hammond, get up close and personal with brilliant marine life at Shedd Aquarium, get curious at Museum of Science and Industry, and make a trip to Skydeck Chicago - Willis Tower.

For where to stay, photos, maps, and other tourist information, refer to the Chicago planner.

Fly from Omaha to Chicago in 4.5 hours. Alternatively, you can drive; or take a train. Expect somewhat warmer evenings in Chicago when traveling from Omaha in December, with lows around 26°F. Finish your sightseeing early on the 1st (Wed) to allow enough time to travel to Cleveland.

Things to do in Chicago

Museums · Childrens Museums · Parks · Zoos & Aquariums

Side Trips

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 ©

Forest City

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.
Change things up with these side-trips from Cleveland: Hard Rock Rocksino Northfield Park (in Northfield), Hundley Cellars (in Geneva) and Barrel Run Crossing Winery (in Rootstown). There's much more to do: enjoy some friendly competition at Bay Lanes Bowling, examine the collection at Rock & Roll Hall of Fame, wander the streets of University Circle, and admire the masterpieces at The Cleveland Museum of Art.

For other places to visit, reviews, and tourist information, read Cleveland travel planning tool.

You can fly from Chicago to Cleveland in 3.5 hours. Alternatively, you can drive; or take a train. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. January in Cleveland sees daily highs of 34°F and lows of 22°F at night. Wrap up your sightseeing on the 4th (Sat) early enough to travel back home.

Things to do in Cleveland

Fun & Games · Casinos · Museums · Wineries

Side Trips

Highlights from your plan
JACK Cleveland Casino ©
JACK Cleveland Casino
Hundley Cellars ©
Hundley Cellars
Barrel Run Crossing Winery ©
Barrel Run Crossing Winery