8 days in Midwest Itinerary

8 days in Midwest Itinerary

Created using Inspirock Midwest visit planner

This plan was created by another inspirock user.  Make it your plan

Route & dates

8 days in Midwest Itinerary

Start: Newark
Fly:  4​h 45​min
1
Chicago
— 2 nights
2
Galena
— 1 night
Drive:  3​h 15​min
3
Winona
— 1 night
Drive:  5​h 15​min
4
Ontonagon
— 1 night
+2
Drive + Fly + Drive:  9​h
5
Custer
— 1 day
Drive + Fly:  7​h 45​min
End: Newark

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You'll explore and learn at The Art Institute of Chicago and Ernest Hemingway Birthplace. Deepen your sense of the past at sights like Millennium Park and Frank Lloyd Wright Home and Studio. Next up on the itinerary: take a stroll through The Magnificent Mile, take in panoramic vistas at Skydeck Chicago - Willis Tower, take in the spiritual surroundings of Fourth Presbyterian Church, and appreciate the history behind Cloud Gate.

For more things to do, where to stay, traveler tips, and more tourist information, go to the Chicago holiday planner.

Newark to Chicago is an approximately 5-hour flight. You can also drive. Traveling from Newark to Chicago, you'll gain 1 hour due to the time zone difference. Expect slightly colder weather when traveling from Newark in November: highs in Chicago hover around 50°F, while lows dip to 35°F. Wrap up your sightseeing on the 22nd (Fri) to allow time to travel to Galena.

Things to do in Chicago

Museums Historic Sites Neighborhoods

Side Trip

Oak Park
Find places to stay Nov 20 — 22:
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
The Field Museum ©
The Field Museum

1
night
Galena

Galena ©
Galena is the largest city in and the county seat of Jo Daviess County, Illinois, with a population of 3,429 at the 2010 census. Start off your visit on the 23rd (Sat): get engrossed in the history at Galena / Jo Daviess County Historical Society and Museum, contemplate the long history of Ulysses S. Grant Home, then brush up on your knowledge of spirits at Blaum Bros. Distilling Co., and finally contemplate the long history of Washburne House State Historic Site.

To find where to stay, ratings, photos, and other tourist information, you can read our Galena attractions planner.

You can fly from Chicago to Galena in 3.5 hours. Other options are to drive; or take a bus. Traveling from Chicago in November, expect Galena to be little chillier, temps between 45°F and 27°F. Finish up your sightseeing early on the 23rd (Sat) so you can travel to Winona.

Things to do in Galena

Historic Sites Breweries & Distilleries Museums
Find places to stay Nov 22 — 23:
Highlights from your plan
Ulysses S. Grant Home ©
Ulysses S. Grant Home
Blaum Bros. Distilling Co. ©
Blaum Bros. Distilling Co.

1
night
Winona

Winona ©
Winona is a city in and the county seat of Winona County, in the state of Minnesota. Kick off your visit on the 24th (Sun): cruise along Garvin Heights, learn about winemaking at ELMARO Vineyard, then explore the world behind art at Minnesota Marine Art Museum, and finally take in the architecture and atmosphere at Basilica of St. Stanislaus Kostka.

To see maps, more things to do, reviews, and other tourist information, refer to the Winona sightseeing planner.

Drive from Galena to Winona in 3.5 hours. In November, plan for daily highs up to 44°F, and evening lows to 29°F. Finish up your sightseeing early on the 24th (Sun) so you can travel to Ontonagon.

Things to do in Winona

Outdoors Scenic Drive Wineries

Side Trip

ELMARO Vineyard
Find places to stay Nov 23 — 24:
Highlights from your plan
Minnesota Marine Art Museum ©
Minnesota Marine Art Museum
ELMARO Vineyard ©
ELMARO Vineyard

1
night
Ontonagon

Ontonagon ©
Ontonagon is a village in the U.S. Start off your visit on the 25th (Mon): admire the sheer force of Bond Falls. On your second day here, contemplate the waterfront views at Lake of the Clouds and then take a peaceful walk through Porcupine Mountains State Park.

To see more things to do, other places to visit, photos, and tourist information, read Ontonagon road trip website .

Traveling by car from Winona to Ontonagon takes 6 hours. Alternatively, you can fly. Due to the time zone difference, you'll lose 1 hour traveling from Winona to Ontonagon. When traveling from Winona in November, plan for slightly colder days and about the same nights in Ontonagon: temperatures range from 39°F by day to 27°F at night. Finish up your sightseeing early on the 26th (Tue) so you can travel to Custer.

Things to do in Ontonagon

Nature Parks Outdoors
Find places to stay Nov 24 — 26:
Highlights from your plan
Bond Falls ©
Bond Falls
Lake of the Clouds ©
Lake of the Clouds
Porcupine Mountains State Park ©
Porcupine Mountains State Park

1
day
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
To see ratings, traveler tips, more things to do, and more tourist information, refer to the Custer journey planner .

Explore your travel options from Ontonagon to Custer with the Route module. The time zone difference when traveling from Ontonagon to Custer is minus 2 hours. When traveling from Ontonagon in November, plan for a bit warmer days in Custer, with highs around 45°F, while nights are about the same with lows around 23°F. Wrap up your sightseeing by early afternoon on the 27th (Wed) to allow time for travel back home.

Things to do in Custer

Nature Parks

Side Trip

Mount Rushmore National Memorial
Find places to stay Nov 26 — 27:
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Custer State Park ©
Custer State Park

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