16 days in Midwest Itinerary

16 days in Midwest Itinerary

Created using Inspirock Midwest route planner

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Route & dates

16 days in Midwest Itinerary

Start: New York City
Fly:  4​h 45​min
1
Milwaukee
— 2 nights
train:  1​h 30​min
2
Chicago
— 4 nights
Fly:  3​h 15​min
3
Saint Louis
— 3 nights
Fly:  4​h
4
Omaha
— 1 night
Fly:  5​h 15​min
5
Rapid City
— 3 nights
Fly:  6​h 15​min
6
Empire
— 1 night
Fly + foot:  5​h 15​min
End: New York City

2
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Get in touch with nature at Atwater Park & Beach and Bender Park Waterfront. When in Milwaukee, make a side trip to see Whistling Straits Golf Course - Straits and Irish in Kohler, approximately 1h 25 min away. And it doesn't end there: explore the landscape on two wheels at Fox Brook Park, contemplate in the serene atmosphere at Basilica of St. Josaphat, and enjoy the sand and surf at Virmond Park.

For where to stay, other places to visit, and more tourist information, you can read our Milwaukee day trip planning tool .

New York City to Milwaukee is an approximately 5-hour flight. You can also do a combination of bus and flight; or drive. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. Traveling from New York City in June, plan for little chillier nights in Milwaukee, with lows around 58°F. Wrap up your sightseeing on the 30th (Sun) early enough to take a train to Chicago.

Things to do in Milwaukee

Outdoors Parks Beaches

Side Trips

Virmond Park, Atwater Park & Beach, Bender Park Waterfront, Whistling Straits Golf Course - Straits and Irish, Fox Brook Park
Highlights from your plan
Fox Brook Park ©
Fox Brook Park
Basilica of St. Josaphat ©
Basilica of St. Josaphat
Virmond Park ©
Virmond Park

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your inner history buff will appreciate Millennium Park and Ernest Hemingway Birthplace. And it doesn't end there: get a taste of the local shopping with The Magnificent Mile, admire the striking features of Frank Lloyd Wright Home and Studio, admire the masterpieces at The Art Institute of Chicago, and engage your brain at Museum of Science and Industry.

For where to stay, traveler tips, ratings, and other tourist information, read Chicago trip planning site .

Take a train from Milwaukee to Chicago in 1.5 hours. Alternatively, you can drive; or take a bus. In June, daily temperatures in Chicago can reach 81°F, while at night they dip to 63°F. Finish your sightseeing early on the 4th (Thu) to allow enough time to travel to Saint Louis.

Things to do in Chicago

Museums Parks Zoos & Aquariums

Side Trips

Oak Park, Horseshoe Hammond
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Museum of Science and Industry ©
Museum of Science and Industry
Wrigley Field ©
Wrigley Field

3
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Get some historical perspective at Cathedral Basilica of Saint Louis and St. Charles Historic District. Escape the urban bustle at Sachs Butterfly House and Riverlands Migratory Bird Sanctuary. The adventure continues: meet the residents at Saint Louis Zoo, examine the collection at City Museum, get your game on at Top Notch Axe Throwing St. Louis, and experience rural life at Grant's Farm.

For maps, ratings, other places to visit, and tourist information, go to the Saint Louis trip itinerary planning site .

Fly from Chicago to Saint Louis in 3.5 hours. Alternatively, you can drive; or take a bus. When traveling from Chicago in July, plan for somewhat warmer days and about the same nights in Saint Louis: temperatures range from 89°F by day to 68°F at night. Finish up your sightseeing early on the 7th (Sun) so you can travel to Omaha.

Things to do in Saint Louis

Parks Wildlife Historic Sites

Side Trips

St. Charles Historic District, Sachs Butterfly House, Riverlands Migratory Bird Sanctuary
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Saint Louis Zoo ©
Saint Louis Zoo
City Museum ©
City Museum

1
night
Omaha

Omaha ©
A major transportation hub, Omaha was once considered little more than a stopping point on a pioneer's journey west.
On the 8th (Mon), get a taste of the local shopping with Old Market, try to win big at Horseshoe Council Bluffs, and then see a show at Henry Doorly Zoo.

To see ratings, more things to do, photos, and other tourist information, read Omaha trip itinerary maker app .

Traveling by flight from Saint Louis to Omaha takes 4 hours. Alternatively, you can drive; or take a bus. July in Omaha sees daily highs of 87°F and lows of 67°F at night. Finish up your sightseeing early on the 8th (Mon) so you can travel to Rapid City.

Things to do in Omaha

Casinos Fun & Games Nightlife

Side Trip

Horseshoe Council Bluffs
Highlights from your plan
Henry Doorly Zoo ©
Henry Doorly Zoo
Horseshoe Council Bluffs ©
Horseshoe Council Bluffs
Old Market ©
Old Market

3
nights
Rapid City

Rapid City ©
South Dakota's second-largest city, Rapid City has for many years served as a gateway to the West.
Take a break from the city and head to Mount Rushmore National Memorial and Bear Country USA. Venture out of the city with trips to Custer (Black Hills National Forest & Custer State Park), Loop Road (in Badlands National Park) and Badlands National Park (in Interior).

To find traveler tips, ratings, and more tourist information, read Rapid City trip itinerary builder tool .

Traveling by flight from Omaha to Rapid City takes 5.5 hours. Alternatively, you can do a combination of shuttle and flight; or drive. The time zone difference when traveling from Omaha to Rapid City is minus 1 hour. Traveling from Omaha in July, plan for a bit cooler nights in Rapid City, with lows around 62°F. Wrap up your sightseeing on the 11th (Thu) to allow time to travel to Empire.

Things to do in Rapid City

Parks Nature Wildlife

Side Trips

Custer, Loop Road, Mount Rushmore National Memorial, Badlands National Park
Highlights from your plan
Mount Rushmore National Memorial ©
Custer State Park ©
Custer State Park
Black Hills National Forest ©
Black Hills National Forest

1
night
Empire

Empire ©
Empire is a village in Leelanau County in the U.S. Start off your visit on the 12th (Fri): enjoy the sand and surf at Lake Michigan Beach Park, get a taste of local nightlife at Lake Ann Brewing Company, and then get to know the fascinating history of Sleeping Bear Dunes National Lakeshore. Get ready for a full day of sightseeing on the 13th (Sat): stroll through Empire Bluff Trail and then enjoy the sand and surf at Platte Point Beach.

For where to stay, ratings, reviews, and other tourist information, refer to the Empire trip builder .

You can do a combination of flight and taxi from Rapid City to Empire in 6.5 hours. Other options are to do a combination of flight, car, and ferry; or drive. Due to the time zone difference, you'll lose 2 hours traveling from Rapid City to Empire. Traveling from Rapid City in July, expect Empire to be little chillier, temps between 75°F and 57°F. Wrap up your sightseeing on the 13th (Sat) early enough to travel back home.

Things to do in Empire

Parks Outdoors Beaches

Side Trips

Lake Ann Brewing Company, Platte Point Beach
Highlights from your plan
Lake Ann Brewing Company ©
Lake Ann Brewing Company

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