10 days in Midwest Itinerary

10 days in Midwest Itinerary

Created using Inspirock Midwest trip itinerary builder

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Route & dates

10 days in Midwest Itinerary

Start: Jacksonville
Drive + Fly:  7​h 45​min
1
Omaha
— 1 night
Fly:  6​h
2
Keystone
— 1 night
Fly:  6​h 15​min
3
Empire
— 1 day
Fly:  3​h 30​min
4
Chicago
— 4 nights
Fly + Drive:  4​h 45​min
5
Youngstown
— 1 day
Drive:  3​h
6
Rockbridge
— 1 night
+2
taxi + Fly + bus:  5​h 30​min
End: Jacksonville

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 4th (Fri), snap pictures at Bob Kerrey Pedestrian Bridge.

To see more things to do, photos, traveler tips, and other tourist information, you can read our Omaha route planner.

Jacksonville to Omaha is an approximately 8-hour combination of car and flight. You can also do a combination of bus and flight; or drive. You'll gain 1 hour traveling from Jacksonville to Omaha due to the time zone difference. Plan for a bit cooler temperatures traveling from Jacksonville in October, with highs in Omaha at 67°F and lows at 45°F. Wrap up your sightseeing on the 5th (Sat) to allow time to travel to Keystone.

Things to do in Omaha

Fun & Games Nightlife Parks

Side Trip

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

1
night
Keystone

Keystone ©
Fewer than 400 people call Keystone home year-round, but the population explodes in summer when crowds flock to nearby Mount Rushmore.
On the 6th (Sun), explore and take pictures at Iron Mountain Road, then tour the pleasant surroundings at Presidential Trail, and then explore and take pictures at Mount Rushmore National Memorial.

For photos, more things to do, other places to visit, and other tourist information, use the Keystone trip planner .

You can fly from Omaha to Keystone in 6 hours. Other options are to drive; or do a combination of shuttle and flight. You'll gain 1 hour traveling from Omaha to Keystone due to the time zone difference. Prepare for little chillier weather when traveling from Omaha in October: high temperatures in Keystone hover around 57°F and lows are around 34°F. Wrap up your sightseeing on the 6th (Sun) early enough to travel to Empire.

Things to do in Keystone

Outdoors Parks Trails

Side Trip

Iron Mountain Road
Highlights from your plan
Mount Rushmore National Memorial ©
Iron Mountain Road ©
Iron Mountain Road
Presidential Trail ©
Presidential Trail

1
day
Empire

Empire ©
Empire is a village in Leelanau County in the U.S. Kick off your visit on the 7th (Mon): visit a coastal fixture at Point Betsie Lighthouse, then trek along Empire Bluff Trail, and then appreciate the extensive heritage of Sleeping Bear Dunes National Lakeshore.

To see photos, ratings, reviews, and tourist information, read Empire trip builder tool .

Traveling by flight from Keystone to Empire takes 6.5 hours. Alternatively, you can do a combination of flight, ferry, and car; or drive. Due to the time zone difference, you'll lose 2 hours traveling from Keystone to Empire. Traveling from Keystone in October, Empire is a bit warmer at night with lows of 43°F. Wrap up your sightseeing on the 7th (Mon) early enough to travel to Chicago.

Things to do in Empire

Parks Historic Sites Trails

Side Trip

Point Betsie Lighthouse
Highlights from your plan
Point Betsie Lighthouse ©
Point Betsie Lighthouse

4
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Magnificent Mile and Millennium Park. Museum-lovers will get to explore The Art Institute of Chicago and Cantigny Park. The adventure continues: try your luck at Horseshoe Hammond, take in nature's colorful creations at Lincoln Park Conservatory, explore and take pictures at Wrigley Field, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see more things to do, traveler tips, maps, and other tourist information, you can read our Chicago trip planner .

Traveling by flight from Empire to Chicago takes 3.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Empire to Chicago. Prepare for a bit warmer weather when traveling from Empire in October: high temperatures in Chicago hover around 65°F and lows are around 49°F. Wrap up your sightseeing on the 11th (Fri) early enough to travel to Youngstown.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trips

Cantigny Park, Horseshoe Hammond
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

1
day
Youngstown

Youngstown ©
Youngstown is a city in and the county seat of Mahoning County in the U.S. Kick off your visit on the 12th (Sat): trek along Mill Creek Park.

For maps, ratings, reviews, and other tourist information, read our Youngstown trip itinerary planning website .

The Route module can help you plan travel from Chicago to Youngstown. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In October, daytime highs in Youngstown are 64°F, while nighttime lows are 45°F. Finish up your sightseeing early on the 12th (Sat) so you can travel to Rockbridge.

Things to do in Youngstown

Trails Wildlife Parks
Highlights from your plan
Mill Creek Park ©
Mill Creek Park

1
night
Rockbridge

Rockbridge is an unincorporated community in eastern Good Hope Township, Hocking County, Ohio, United States. On the 13th (Sun), identify plant and animal life at Conkles Hollow State Nature Preserve and then get interesting insight from Tours.

To find photos, ratings, and other tourist information, read our Rockbridge trip builder app .

Traveling by car from Youngstown to Rockbridge takes 3.5 hours. In October, plan for daily highs up to 67°F, and evening lows to 44°F. Wrap up your sightseeing on the 13th (Sun) early enough to travel back home.

Things to do in Rockbridge

Wildlife Adventure Tours
Highlights from your plan
Zipline
Conkles Hollow State Nature Preserve ©

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