14 days in Continental USA Itinerary

14 days in Continental USA Itinerary

Created using Inspirock United States travel route planner

Make it your trip
Drive
1
Milwaukee
— 1 day
Drive
2
Chicago
— 4 nights
Drive
3
Des Moines
— 1 day
Drive
4
Omaha
— 1 night
Drive
5
Custer
— 2 nights
Drive
6
Medora
— 1 night
Drive
7
Minneapolis
— 1 night
Drive
8
Indianapolis
— 1 day
Drive

S M T W T F S
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Milwaukee

— 1 day

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Start off your visit on the 11th (Sat): examine the collection at Harley-Davidson Museum, then get engrossed in the history at Chudnow Museum of Yesteryear, and then sample the tasty concoctions at Lakefront Brewery.

To find photos, traveler tips, and tourist information, read Milwaukee tour itinerary tool.

Cleveland to Milwaukee is an approximately 5.5-hour flight. You can also drive; or take a train. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In September in Milwaukee, expect temperatures between 74°F during the day and 58°F at night. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Chicago.

Things to do in Milwaukee

Museums · Breweries & Distilleries · Shopping

Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, make a trip to Millennium Park, take in the waterfront at Navy Pier, and get curious at Museum of Science and Industry.

Discover how to plan a Chicago trip in just a few steps with Inspirock's itinerary builder.

Traveling by car from Milwaukee to Chicago takes 2 hours. Alternatively, you can drive; or take a train; or take a bus. In September in Chicago, expect temperatures between 78°F during the day and 61°F at night. Cap off your sightseeing on the 15th (Wed) early enough to travel to Des Moines.

Things to do in Chicago

Museums · Parks · Zoos & Aquariums · Theme Parks

Des Moines

— 1 day
Des Moines is the capital and the most populous city in the U.S. state of Iowa. Kick off your visit on the 16th (Thu): ponder the world of politics at Capitol Building, get to know the resident critters at Blank Park Zoo, and then stroll around Pappajohn Sculpture Park.

To find more things to do, maps, traveler tips, and tourist information, use the Des Moines trip itinerary builder tool.

You can drive from Chicago to Des Moines in 6 hours. Alternatively, you can fly; or drive; or take a bus. In September, daytime highs in Des Moines are 80°F, while nighttime lows are 60°F. Cap off your sightseeing on the 16th (Thu) early enough to go by car to Omaha.

Things to do in Des Moines

Parks · Zoos & Aquariums

Omaha

— 1 night

Gateway to the West

A major transportation hub, Omaha was once considered little more than a stopping point on a pioneer's journey west.
On the 17th (Fri), try your luck at Horseshoe Council Bluffs, then get up close and personal with brilliant marine life at Henry Doorly Zoo, and then get a taste of the local shopping with Old Market.

To see photos, traveler tips, other places to visit, and more tourist information, you can read our Omaha planner.

Drive from Des Moines to Omaha in 2.5 hours. Alternatively, you can take a bus. September in Omaha sees daily highs of 81°F and lows of 59°F at night. Finish your sightseeing early on the 17th (Fri) to allow enough time to travel to Custer.

Things to do in Omaha

Neighborhoods · Nightlife · Casinos · Fun & Games

Side Trip

Custer

— 2 nights
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Take a break from Custer with a short trip to Presidential Trail in Keystone, about 30 minutes away. There's still lots to do: explore the striking landscape of Mount Rushmore National Memorial, contemplate the waterfront views at Sylvan Lake, cruise along Wildlife Loop Road, and get a taste of the local shopping with Insideout.

To see more things to do, other places to visit, traveler tips, and other tourist information, you can read our Custer tour builder tool.

Traveling by flight from Omaha to Custer takes 7 hours. Alternatively, you can drive; or do a combination of bus and taxi. The time zone difference moving from Central Standard Time (CST) to Mountain Standard Time (MST) is minus 1 hour. Prepare for slightly colder weather when traveling from Omaha in September: high temperatures in Custer hover around 71°F and lows are around 45°F. Wrap up your sightseeing on the 20th (Mon) early enough to drive to Medora.

Things to do in Custer

Outdoors · Parks · Scenic Drive · Nature

Side Trips

Medora

— 1 night
Medora is a city in Billings County, North Dakota, United States. Start off your visit on the 21st (Tue): get to know the fascinating history of South Unit.

To find more things to do, ratings, reviews, and other tourist information, go to the Medora journey website.

Traveling by car from Custer to Medora takes 5.5 hours. Alternatively, you can fly; or do a combination of taxi and bus. In September in Medora, expect temperatures between 70°F during the day and 44°F at night. Finish up your sightseeing early on the 21st (Tue) so you can travel to Minneapolis.

Things to do in Medora

Nature · Parks · Historic Sites

Side Trip

Highlights from your trip

Minneapolis

— 1 night

The City of Lakes

Located on both banks of the Mississippi River, Minneapolis salutes the state's love of the outdoors with numerous lakes, wetlands, creeks, and waterfalls--many connected to one another by a national scenic byway great for sightseeing.
Start off your visit on the 22nd (Wed): explore the activities along Chain of Lakes, then admire the natural beauty at Minneapolis Sculpture Garden, then stroll around Minnehaha Park, and finally examine the collection at Como-Harriet Streetcar Line. On your second day here, get to know the resident critters at Como Park Zoo & Conservatory, grab your bike and head to Mill Ruins Park, then get engrossed in the history at Mill City Museum, and finally explore the world behind art at Minneapolis Institute of Art.

To see traveler tips, where to stay, ratings, and more tourist information, go to the Minneapolis planner.

You can drive from Medora to Minneapolis in 9 hours. Other options are to do a combination of car and flight; or drive; or do a combination of taxi and bus. The time zone difference moving from Mountain Standard Time to Central Standard Time is 1 hour. Expect a bit warmer evenings in Minneapolis when traveling from Medora in September, with lows around 57°F. Wrap up your sightseeing on the 23rd (Thu) to allow time to travel to Indianapolis.

Things to do in Minneapolis

Parks · Museums · Nature · Fun & Games

Side Trip

Indianapolis

— 1 day

Circle City

Indiana's capital and most populous city, Indianapolis is best known for its racecar events and impressive museums, and as the hometown of Kurt Vonnegut.
Kick off your visit on the 24th (Fri): make a trip to USS Indianapolis Memorial, see the interesting displays at Indianapolis Motor Speedway Museum, then don't miss a visit to Central Canal, and finally don't miss a visit to Monument Circle.

To find maps, where to stay, ratings, and tourist information, go to the Indianapolis journey planner.

You can drive from Minneapolis to Indianapolis in 10 hours. Alternatively, you can fly; or drive; or take a bus. You'll lose 1 hour traveling from Minneapolis to Indianapolis due to the time zone difference. In September in Indianapolis, expect temperatures between 80°F during the day and 59°F at night. Finish your sightseeing early on the 24th (Fri) so you can drive back home.

Things to do in Indianapolis

Museums

Wisconsin travel guide

4.2
Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.

Illinois travel guide

4.4
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.

Iowa travel guide

4.1
Casinos · Historic Sites · Specialty Museums
The Hawkeye State
Part of the American heartland, Iowa is marked by a strong agricultural heritage, with farmland encompassing around 90 percent of the state's land. However, a holiday in Iowa offers more than corn and cows: you'll also discover charming towns, beautiful lakes, and a handful of vibrant cities. Iowa City, a university town, provides a healthy dose of culture and nightlife, with a youthful and artistic vibe fueled by a sizable student population. A trip to some of Iowa's small towns provides a true American experience. Fortunately, the welcoming residents bear very little resemblance to the dour Iowans portrayed in Grant Wood's famous painting "American Gothic."

Nebraska travel guide

4.6
Aquariums · Shopping · History Museums
The Cornhusker State
Situated in the heartland of America, Nebraska is home to a large number of small rural communities and masses of farmland. The state's two main cities, Omaha and Lincoln, are abuzz with youthful energy and cultural delights. Your itinerary can include a trip to the cities' museums to learn about the state's past, or tours of the area's important pioneer and Native American sites. The state's central location means that it has been crossed by many trails, but it was the California Gold Rush of 1848-1855 that originally brought large numbers of non-indigenous people to the area. Scenic river valleys offer plenty of opportunities for outdoor vacation activities, while Nebraska's agricultural towns charm visitors with their all-American spirit.

South Dakota travel guide

4.2
National Parks · Scenic Drive · Monuments
The State of Great Faces and Great Places
Famous for the cliffside monuments of Mount Rushmore and the Crazy Horse memorial, South Dakota is a land of Old West history, American Indian culture, and impressive natural wonders. Get to know the state's diverse and breathtaking landscape with a trip through Custer National Park, with a herd of 1,300 free-roaming bison, or by traversing the dramatic peaks of Badlands National Park near the Black Hills. Allow time in your itinerary to visit the state's largest city, Sioux Falls, for shopping, dining, and entertainment options, as well as a number of museums and historical attractions.

North Dakota travel guide

4.6
National Parks · History Museums · Historic Sites
Geographic Center of the North American Continent
A primarily rural state, North Dakota is the ancient home of the Lakota tribe. Norwegian settlers once made up the European population, and one of the state's major attractions is the Norsk Høstfest, the largest Norwegian festival in the United States. The vast plains and never-ending sky inspire the many orchestras that call the state home. The spirituality of the music is second only to the spirituality of the people, as the state has the nation's highest percentage of churchgoing residents. The state's open fields are conducive to fishing, hunting, and winter activities.

Minnesota travel guide

4.4
Shopping Malls · Room Escape Games · Entertainment Centers
The Land of 10,000 Lakes
Deriving its name from the Dakota word for "land of sky-tinted water," Minnesota is a land of pristine lakes, pockets of dense green forests, and sprawling prairieland. Spend your vacation exploring the state's diverse landscape for endless outdoor activity and a chance to see some of the area's national monuments, or take a trip to the bustling St. Paul-Minneapolis area, a network of commerce and cultural attractions, including the famous Mall of America.

Indiana travel guide

4.1
Casinos · Room Escape Games · Specialty Museums
The Hoosier State
With an extensive history of motorsports, Indiana's main claim to fame is the popular automobile race held each year in its capital city. A mostly rural state, Indiana is a land of till plains and lakes, its appearance a result of traces left behind by receding glaciers. The central section of the state, mostly flat with some rolling hills, contains some of the country's most fertile farmland. The state also contains almost 39,000 km (24,000 mi) of waterways, including the Wabash River, the longest free-flowing river east of the Mississippi. For a genuine "Hoosier" experience, tour the state's slow-paced small towns, noted for their hospitality and outstanding local cuisine. You'll remember the warmth and charm long after your vacation is over.