10 days in Midwest Itinerary

10 days in Midwest Itinerary

Created using Inspirock Midwest holiday builder

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Route & dates

10 days in Midwest Itinerary

Start: Chicago
Fly + taxi:  5​h 15​min
1
Custer
— 1 night
taxi + Fly:  6​h 30​min
2
Omaha
— 1 day
Fly:  4​h
3
Saint Louis
— 2 nights
Fly:  3​h 15​min
4
Milwaukee
— 1 night
Drive:  2​h 30​min
5
Hart
— 2 nights
Drive:  3​h 30​min
6
Chicago
— 2 nights
End: Chicago

1
night
Custer

Custer ©
Generally considered to be the oldest town established by European Americans in the Black Hills, Custer began as a mining town.
Kick off your visit on the 20th (Thu): explore the activities along Sylvan Lake and then explore the striking landscape at Needles Eye Tunnel. On the 21st (Fri), you'll have a packed day of sightseeing: explore the striking landscape of Mount Rushmore National Memorial, get a taste of the local shopping with Warrior's Work & Ben West Gallery, then look for all kinds of wild species at Black Hills National Forest, and finally immerse yourself in nature at Custer State Park.

To see where to stay, photos, traveler tips, and tourist information, go to the Custer online trip builder .

Chicago to Custer is an approximately 5.5-hour combination of flight and taxi. You can also drive; or do a combination of train and bus. The time zone difference moving from Central Standard Time to Mountain Standard Time is minus 1 hour. Traveling from Chicago in June, things will get a bit cooler in Custer: highs are around 73°F and lows about 48°F. Finish your sightseeing early on the 21st (Fri) to allow enough time to travel to Omaha.

Things to do in Custer

Parks Nature Wildlife

Side Trips

Warrior's Work & Ben West Gallery, Mount Rushmore National Memorial
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Custer State Park ©
Custer State Park
Black Hills National Forest ©
Black Hills National Forest

1
day
Omaha

Omaha ©
A major transportation hub, Omaha was once considered little more than a stopping point on a pioneer's journey west.
On the 22nd (Sat), shop like a local with Old Market, then try your luck at Horseshoe Council Bluffs, and then see a show at Henry Doorly Zoo.

For photos, ratings, maps, and other tourist information, you can read our Omaha travel route planner.

Traveling by combination of taxi and flight from Custer to Omaha takes 6.5 hours. Alternatively, you can do a combination of car and flight; or drive. The time zone difference when traveling from Custer to Omaha is 1 hour. Plan for somewhat warmer temperatures traveling from Custer in June, with highs in Omaha at 85°F and lows at 64°F. Finish your sightseeing early on the 22nd (Sat) to allow enough time to travel to Saint Louis.

Things to do in Omaha

Parks Fun & Games Casinos

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

2
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
On the 23rd (Sun), admire the natural beauty at Missouri Botanical Garden, get your game on at Top Notch Axe Throwing St. Louis, then enjoy breathtaking views from The Gateway Arch, and finally take in the architecture and atmosphere at Cathedral Basilica of Saint Louis. Get ready for a full day of sightseeing on the 24th (Mon): examine the collection at City Museum, then get to know the resident critters at Saint Louis Zoo, and then appreciate the extensive heritage of St. Charles Historic District.

Start your trip to Saint Louis by creating a personalized itinerary on Inspirock.

Traveling by flight from Omaha to Saint Louis takes 4 hours. Alternatively, you can drive; or take a bus. In June, daytime highs in Saint Louis are 87°F, while nighttime lows are 67°F. Finish your sightseeing early on the 24th (Mon) so you can travel to Milwaukee.

Things to do in Saint Louis

Parks Zoos & Aquariums Historic Sites

Side Trip

St. Charles Historic District
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Cathedral Basilica of Saint Louis
City Museum ©
City Museum
Missouri Botanical Garden ©
Missouri Botanical Garden

1
night
Milwaukee

Milwaukee
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Kick off your visit on the 25th (Tue): tour the pleasant surroundings at Bender Park Waterfront, kick back and relax at Virmond Park, and then enjoy the sand and surf at Atwater Park & Beach.

For maps, reviews, more things to do, and tourist information, refer to the Milwaukee trip itinerary maker website .

Traveling by flight from Saint Louis to Milwaukee takes 3.5 hours. Alternatively, you can do a combination of flight and bus; or drive. Prepare for little chillier weather when traveling from Saint Louis in June: high temperatures in Milwaukee hover around 76°F and lows are around 58°F. Cap off your sightseeing on the 25th (Tue) early enough to travel to Hart.

Things to do in Milwaukee

Parks Outdoors Beaches

Side Trips

Atwater Park & Beach, Bender Park Waterfront, Virmond Park

2
nights
Hart

Hart ©
Hart is a city in the U.S. On the 26th (Wed), look for gifts at Dublin General Store LTD, then enjoy the sand and surf at Fifth Avenue Beach, and then enjoy the sand and surf at Stearns Park. Here are some ideas for day two: tee off at Golden Sands Golf Course and then kick back and relax at Silver Lake State Park.

To see traveler tips, ratings, more things to do, and tourist information, read Hart trip itinerary maker app .

Traveling by car from Milwaukee to Hart takes 5.5 hours. You'll lose 1 hour traveling from Milwaukee to Hart due to the time zone difference. Traveling from Milwaukee in June, Hart is a bit cooler at night with lows of 53°F. Finish your sightseeing early on the 27th (Thu) so you can travel to Chicago.

Things to do in Hart

Outdoors Parks Beaches

Side Trips

Fifth Avenue Beach, Stearns Park, Golden Sands Golf Course, Dublin General Store LTD
Highlights from your plan
Fifth Avenue Beach ©
Fifth Avenue Beach

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 28th (Fri): appreciate the history behind Cloud Gate, admire the masterpieces at The Art Institute of Chicago, then admire all the interesting features of Millennium Park, and finally take a stroll through The Magnificent Mile. Get ready for a full day of sightseeing on the 29th (Sat): engage your brain at Museum of Science and Industry, then see the interesting displays at The Field Museum, and then enjoy breathtaking views from Skydeck Chicago - Willis Tower.

To see ratings, photos, other places to visit, and more tourist information, refer to the Chicago trip planner.

You can drive from Hart to Chicago in 4 hours. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Plan for a bit warmer temperatures traveling from Hart in June, with highs in Chicago at 81°F and lows at 63°F. Finish your sightseeing early on the 29th (Sat) to allow enough time to travel back home.

Things to do in Chicago

Museums Shopping Neighborhoods
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park
The Field Museum ©
The Field Museum

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