11 days in Midwest Itinerary

11 days in Midwest Itinerary

Created using Inspirock Midwest trip planner

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Route & dates

11 days in Midwest Itinerary

Start: Tampa
Fly:  4​h 45​min
1
Saint Louis
— 2 nights
Fly + Drive:  3​h 45​min
2
Branson
— 2 nights
Fly + taxi:  6​h 15​min
3
Custer
— 1 night
taxi + Fly:  6​h 45​min
4
Empire
— 1 day
Fly:  3​h 30​min
5
Chicago
— 3 nights
train:  1​h 30​min
6
Milwaukee
— 1 night
Fly:  5​h 30​min
End: Tampa

2
nights
Saint Louis

Saint Louis ©
Test the local claim that Saint Louis is second only to Washington, D.C.
Get some historical perspective at Cathedral Basilica of Saint Louis and Missouri Botanical Garden. Step out of the city life by going to Powder Valley Conservation Nature Center and Parasailing & Paragliding. There's still lots to do: take in panoramic vistas at The Gateway Arch, brush up on your knowledge of spirits at StilL 630 Distillery, stop by Ted Drew's Frozen Custard, and look for all kinds of wild species at Bee tree park.

To see traveler tips, other places to visit, ratings, and tourist information, refer to the Saint Louis itinerary planner.

Tampa to Saint Louis is an approximately 5-hour flight. You can also drive; or take a bus. You'll gain 1 hour traveling from Tampa to Saint Louis due to the time zone difference. Expect little chillier temperatures when traveling from Tampa in August; daily highs in Saint Louis reach 87°F and lows reach 66°F. Finish your sightseeing early on the 5th (Mon) so you can travel to Branson.

Things to do in Saint Louis

Parks Wildlife Historic Sites
Highlights from your plan
Cathedral Basilica of Saint Louis ©
Missouri Botanical Garden ©
Missouri Botanical Garden
Ted Drew's Frozen Custard ©
Ted Drew's Frozen Custard

2
nights
Branson

Branson ©
Nestled in Missouri's beautiful Ozark Mountains lies one of the country's most attractive vacation towns for year-round family entertainment.
Kick off your visit on the 6th (Tue): identify plant and animal life at Shepherd of the Hills Fish Hatchery, take some stellar pictures from College of the Ozarks, then buy something for everyone on your list at Branson Landing, and finally admire the local landmark of Dancing Water Fountain. On your second day here, whizz through the canopy at some of the top local zipline courses and adventure parks, do a tasting at Stone Hill Winery, then take a stroll through Historic Downtown Branson, and finally take in the architecture and atmosphere at Our Lady of the Lake Catholic Church.

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

You can do a combination of flight and car from Saint Louis to Branson in 4 hours. Other options are to drive; or take a bus. In August, plan for daily highs up to 85°F, and evening lows to 66°F. Cap off your sightseeing on the 7th (Wed) early enough to travel to Custer.

Things to do in Branson

Parks Wildlife Historic Sites
Highlights from your plan
Our Lady of the Lake Catholic Church ©
Shepherd of the Hills Fish Hatchery ©
Zipline

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.
On the 8th (Thu), contemplate the waterfront views at Sylvan Lake, explore the wealth of natural beauty at Mount Rushmore National Memorial, and then delve into the lush surroundings at Black Hills National Forest.

To see other places to visit, ratings, photos, and other tourist information, read Custer route website .

You can do a combination of flight and taxi from Branson to Custer in 6.5 hours. Other options are to do a combination of car, flight, and taxi; or drive. Due to the time zone difference, you'll gain 1 hour traveling from Branson to Custer. Prepare for slightly colder weather when traveling from Branson in August: high temperatures in Custer hover around 77°F and lows are around 51°F. Finish your sightseeing early on the 8th (Thu) to allow enough time to travel to Empire.

Things to do in Custer

Nature Parks Wildlife

Side Trip

Mount Rushmore National Memorial
Highlights from your plan
Mount Rushmore National Memorial ©
Mount Rushmore National Memorial
Black Hills National Forest ©
Black Hills National Forest
Sylvan Lake ©
Sylvan Lake

1
day
Empire

Empire ©
Empire is a village in Leelanau County in the U.S. Kick off your visit on the 9th (Fri): stroll through Lake Michigan Beach Park, get to know the fascinating history of Sleeping Bear Dunes National Lakeshore, and then join in the after-dark buzz at Lake Ann Brewing Company.

To find traveler tips, photos, and more tourist information, you can read our Empire trip site .

Traveling by combination of taxi and flight from Custer to Empire takes 7 hours. Alternatively, you can do a combination of taxi, flight, ferry, and car; or drive. You'll lose 2 hours traveling from Custer to Empire due to the time zone difference. Traveling from Custer in August, you can expect nighttime temperatures to be somewhat warmer in Empire, with lows of 58°F. Cap off your sightseeing on the 9th (Fri) early enough to travel to Chicago.

Things to do in Empire

Parks Historic Sites Wildlife

Side Trip

Lake Ann Brewing Company
Highlights from your plan
Lake Ann Brewing Company ©
Lake Ann Brewing Company

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Get in touch with nature at Kathy Osterman Beach and Chicago Lakefront. The adventure continues: take a stroll through The Magnificent Mile, add some adventure to your tour with a kayaking and canoeing tour, take in panoramic vistas at Skydeck Chicago - Willis Tower, and admire the masterpieces at The Art Institute of Chicago.

For where to stay, reviews, ratings, and tourist information, read Chicago online itinerary planner .

Traveling by flight from Empire to Chicago takes 3.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. The time zone difference when traveling from Empire to Chicago is minus 1 hour. Traveling from Empire in August, expect Chicago to be a bit warmer, temps between 83°F and 67°F. Wrap up your sightseeing on the 12th (Mon) early enough to take a train to Milwaukee.

Things to do in Chicago

Outdoors Parks Museums
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
Lakefront Trail ©
Lakefront Trail
Kayaking & Canoeing

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 13th (Tue): stop by Indulgence Chocolatiers, indulge your thirst for a good beer at Lakefront Brewery, then take in the spiritual surroundings of Basilica of St. Josaphat, and finally examine the collection at Harley-Davidson Museum.

To find maps, photos, other places to visit, and more tourist information, use the Milwaukee trip itinerary tool .

Take a train from Chicago to Milwaukee in 1.5 hours. Alternatively, you can drive; or take a bus. In August in Milwaukee, expect temperatures between 79°F during the day and 64°F at night. Wrap up your sightseeing on the 13th (Tue) to allow time to travel back home.

Things to do in Milwaukee

Breweries & Distilleries Museums Historic Sites
Highlights from your plan
Lakefront Brewery ©
Lakefront Brewery
Basilica of St. Josaphat ©
Basilica of St. Josaphat
Indulgence Chocolatiers ©
Indulgence Chocolatiers

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