7 days in Midwest Itinerary

7 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary builder

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Route & dates

7 days in Midwest Itinerary

Start: Des Moines
bus:  2​h 15​min
1
Omaha
— 1 day
Fly:  4​h 15​min
2
Chicago
— 3 nights
Drive:  3​h 45​min
3
Hart
— 2 nights
Drive:  5​h 15​min
4
Milwaukee
— 1 night
bus + Fly:  4​h 15​min
End: Des Moines

1
day
Omaha

Omaha ©
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 1st (Sun): try to win big at Horseshoe Council Bluffs and then observe the fascinating underwater world at Henry Doorly Zoo.

To find reviews, maps, ratings, and tourist information, go to the Omaha trip site .

Des Moines to Omaha is an approximately 2.5-hour bus ride. You can also drive. In September in Omaha, expect temperatures between 81°F during the day and 59°F at night. Wrap up your sightseeing on the 1st (Sun) early enough to travel to Chicago.

Things to do in Omaha

Fun & Games Casinos Parks

Side Trip

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

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
We've included these beaches for you: Rosewood Beach and Whihala Beach. Next up on the itinerary: admire the masterpieces at The Art Institute of Chicago, get curious at Museum of Science and Industry, try your luck at Horseshoe Hammond, and admire the landmark architecture of Rockefeller Memorial Chapel.

To see traveler tips, photos, reviews, and tourist information, go 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. In September, daily temperatures in Chicago can reach 78°F, while at night they dip to 61°F. Finish your sightseeing early on the 4th (Wed) so you can travel to Hart.

Things to do in Chicago

Parks Beaches Outdoors

Side Trips

Horseshoe Hammond, Rosewood Beach, Whihala Beach
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Horseshoe Hammond ©
Horseshoe Hammond
Whihala Beach ©
Whihala Beach

2
nights
Hart

Hart ©
Hart is a city in the U.S. Kick off your visit on the 5th (Thu): enjoy the sand and surf at Stearns Park and then stroll through Fifth Avenue Beach. Here are some ideas for day two: enjoy the sand and surf at Pere Marquette Park and then enjoy the sand and surf at Silver Lake State Park Pedestrian Dune Access.

To see where to stay, other places to visit, and tourist information, refer to the Hart driving holiday planner .

You can drive from Chicago to Hart in 4 hours. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Hart. Prepare for little chillier weather when traveling from Chicago in September: high temperatures in Hart hover around 72°F and lows are around 52°F. Wrap up your sightseeing on the 6th (Fri) early enough to travel to Milwaukee.

Things to do in Hart

Parks Beaches Outdoors

Side Trips

Fifth Avenue Beach, Stearns Park, Pere Marquette Park
Highlights from your plan
Fifth Avenue Beach ©
Fifth Avenue Beach

1
night
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
On the 7th (Sat), explore the landscape on two wheels at Fox Brook Park and then kick back and relax at Atwater Park & Beach.

To find reviews, traveler tips, other places to visit, and tourist information, use the Milwaukee attractions planning tool .

Traveling by car from Hart to Milwaukee takes 4 hours. The time zone difference when traveling from Hart to Milwaukee is minus 1 hour. Expect a bit warmer evenings in Milwaukee when traveling from Hart in September, with lows around 58°F. Finish up your sightseeing early on the 7th (Sat) so you can travel back home.

Things to do in Milwaukee

Parks Beaches Outdoors

Side Trips

Fox Brook Park, Atwater Park & Beach
Highlights from your plan
Fox Brook Park ©
Fox Brook Park

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