My first trip to the USA became a moment that changed my life. I was amazed by the scale of the country, the contrast of its cities, and the incredible energy of the people. Since then, I have explored America from coast to coast: driven legendary highways, hiked national parks, and discovered hundreds of places you won't find in typical guides. Today I create personalized USA itineraries so you can experience the real America – vibrant, dynamic, and unforgettable. Let me design a trip that fits you perfectly.

The Midwest, often referred to as America’s Heartland, offers an extraordinary array of attractions, rich history, and vibrant culture. Whether you’re drawn to bustling cities, serene lakeshores, or the rolling hills of the countryside, the Midwest has something for everyone. This article will guide you through six must-visit cities, recommend the best modes of transport, and provide a comprehensive 10-day itinerary, along with essential tips for tourists.

Cities and Attractions

Chicago, Illinois

Chicago, the starting point of many Midwest adventures, is known for its stunning architecture, vibrant arts scene, and rich history. Key attractions include:

  • Cloud Gate (The Bean): An iconic sculpture in Millennium Park.
  • Navy Pier: Offers shops, restaurants, and the Centennial Wheel.
  • The Art Institute of Chicago: Home to an extensive collection of art.
  • Magnificent Mile: A shopper’s paradise with upscale stores and eateries.

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Minneapolis, Minnesota

Minneapolis is a city of lakes and a hub for culture and the arts.

  • Minneapolis Sculpture Garden: Featuring the famous Spoonbridge and Cherry.
  • Walker Art Center: One of the top contemporary art museums.
  • Minnehaha Park: Home to the stunning Minnehaha Falls.

Milwaukee, Wisconsin

Milwaukee is known for its breweries, historic sites, and vibrant neighborhoods.

  • Milwaukee Public Market: Offers a variety of local foods and goods.
  • Milwaukee Art Museum: Notable for its impressive architecture.
  • Harley-Davidson Museum: Celebrates the iconic motorcycle brand.

Dubuque, Iowa

A charming town along the Mississippi River with a rich industrial history.

  • Fenelon Place Elevator: The world’s shortest, steepest scenic railway.
  • National Mississippi River Museum & Aquarium: Offers interactive exhibits about the river’s ecosystem.
  • Downtown Murals: Over forty murals depicting the town’s history and culture.

Marquette, Michigan

Located in Michigan’s Upper Peninsula, Marquette is a gateway to natural beauty.

  • Pictured Rocks National Lakeshore: Famous for its multicolored cliffs.
  • Marquette Maritime Museum: Offers insights into the maritime history of Lake Superior.
  • Presque Isle Park: Provides breathtaking views of Lake Superior.\

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South Bend, Indiana

South Bend is home to the University of Notre Dame and other historic sites.

  • University of Notre Dame: Known for its beautiful campus and Basilica of the Sacred Heart.
  • Studebaker National Museum: Showcases classic cars and the history of the Studebaker Corporation.
  • Potawatomi Zoo: Indiana’s oldest zoo, perfect for family visits.

Best Time to Travel in the Midwest

The Midwest offers unique experiences in every season, but the best time to travel depends on your interests and the type of activities you enjoy. Here’s a seasonal breakdown to help you decide when to visit:

Spring (March to May)

  • Weather: Temperatures range from cool to mild, with blooming flowers and budding trees.
  • Pros: Fewer crowds, lower prices, and vibrant spring festivals.
  • Activities: Ideal for exploring parks, gardens, and outdoor attractions without the summer heat.

Summer (June to August)

  • Weather: Warm to hot temperatures, with occasional thunderstorms.
  • Pros: Long daylight hours, numerous festivals, and outdoor activities.
  • Activities: Perfect for lake activities, beach visits, hiking, and attending outdoor events like music festivals and fairs.

About Us

Since 2015, our website has specialized in individual planning of unique routes, taking into account personal preferences and desires.

Each of you will receive a unique PDF file from us, which contains everything you need: travel routes, car rentals, hotels, the best tourist attractions, attractions for kids and everything you need for a perfect vacation.

During the trip, we are available for you by phone via WhatsApp.

Our personal service provides information from A to Z, taking into account many small details that can become a decisive factor on the way from a wasted trip to an unforgettable vacation.

Our service will make your trip comfortable, save a lot of time on planning and preparation, and most importantly – will allow you to become freer and fully enjoy the pleasure of the trip.

Fall (September to November)

  • Weather: Mild temperatures with crisp, cool air and stunning fall foliage.
  • Pros: Beautiful scenery, harvest festivals, and comfortable temperatures for outdoor exploration.
  • Activities: Great for scenic drives, apple picking, and visiting pumpkin patches. Fall is also an excellent time for hiking and photography.

Winter (December to February)

  • Weather: Cold temperatures with snowfall, particularly in the northern regions.
  • Pros: Winter sports, festive holiday events, and cozy indoor attractions.
  • Activities: Ideal for skiing, snowboarding, ice skating, and enjoying holiday markets and light displays. Cities like Chicago and Minneapolis have vibrant winter activities and events.

Best Transport to Travel around the Midwest

Traveling through the Midwest is best done by car, which offers the flexibility to explore both urban and rural areas at your own pace. Major highways and scenic byways connect the region’s cities and attractions, making road trips an ideal way to experience the Heartland. For those preferring public transport, cities like Chicago, Minneapolis, and Milwaukee have extensive public transit systems, including buses, trains, and light rail.

10-Day Midwest Itinerary

Day 1-2: Chicago, Illinois

  • Explore Millennium Park, Navy Pier, and the Art Institute.
  • Enjoy a river cruise to see the architectural wonders.

Day 3: Dubuque, Iowa

  • Visit the National Mississippi River Museum & Aquarium.
  • Ride the Fenelon Place Elevator and explore downtown murals.

Day 4-5: Minneapolis, Minnesota

  • Discover the Minneapolis Sculpture Garden and Walker Art Center.
  • Visit Minnehaha Park and take a stroll around the lakes.

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Day 6-7: Bayfield, Wisconsin & Apostle Islands

  • Explore Bayfield’s charm and take a boat tour of the Apostle Islands.
  • Enjoy a relaxing day on the lake with options for kayaking or sailing.

Day 8: Marquette, Michigan

  • Tour Pictured Rocks National Lakeshore by boat.
  • Visit the Marquette Maritime Museum and Presque Isle Park.

Day 9: Milwaukee, Wisconsin

  • Wander through the Milwaukee Public Market and Riverwalk.
  • Visit the Milwaukee Art Museum and Harley-Davidson Museum.

Day 10: South Bend, Indiana

  • Explore the University of Notre Dame and its historic buildings.
  • Visit the Studebaker National Museum before heading back.

Tips for Tourists

  • Pack for Varied Weather: The Midwest experiences a wide range of weather conditions. Bring layers to adapt to changing temperatures.
  • Rent a Car: For the most flexibility and to reach less accessible destinations, renting a car is highly recommended.
  • Check Local Events: Many cities have seasonal festivals and events that can enhance your visit.
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  • Try Local Cuisine: Don’t miss out on regional specialties like Chicago deep-dish pizza, Wisconsin cheese, and Minnesota wild rice dishes.
  • Stay Hydrated: Especially in the summer, make sure to drink plenty of water while exploring.
  • Use Navigation Apps: Apps like Google Maps or Waze can help navigate through unfamiliar areas and avoid traffic.

What we propose

Emma Heidi - Itinerary Expert

Emma Heidi


Customer Experience Manager

Take all the stress out of planning your trip!

With our experts, you can create the perfect itinerary for you – complete, comfortable, and tailored to all your dreams, wishes, and needs.

We take care of every little detail, so you can simply focus on enjoying your journey.

We’ve been designing personalized itineraries since 2015, and over the years we’ve created thousands of custom itineraries for happy clients.

Discover our clients’ experiences here

 Save time, avoid confusion – we do the work for you. Our service saves you weeks of searching, reading, comparing, and complicated planning. Instead of wasting endless hours – you receive a ready-to-use, accurate and clear itinerary.

 A tailor-made itinerary – built just for you. Your itinerary is personally designed based on our experts’ real field experience and genuine feedback from hundreds of travelers – including hidden discoveries and insider tips that don’t appear in any travel guide.

 Smart accommodation selection – often saves you hundreds or even thousands of dollars. We help you choose verified and recommended places to stay, checking availability for your exact travel dates. Sometimes we suggest hotels not “in the center,” but in safe, convenient, and highly strategic locations – which can significantly reduce travel costs and save you even thousands of dollars.

 We’re by your side even during the trip. We stay with you throughout your vacation – providing professional help whenever needed. If the weather changes, there’s a strike, a local event, heavy crowds, or any unexpected situation – we are here to update, guide, and adjust your itinerary in real time.

 Easy-to-use itinerary – with direct navigation links. Your itinerary includes direct Waze / Google Maps links – no need to search for parking addresses, no stress, no mistakes. Just tap – and go.


Service cost: from only $420. (Special price for short itineraries up to 5 days). Clients tell us the itinerary saves them costly mistakes, fines, wrong choices – plus exclusive discounts on car rentals, better-priced accommodations, and money-saving local tips.

Want to know if it’s really worth it?

Take a look at the experiences of travelers who built their personal itinerary with us.

Click here and let’s start building the itinerary that will save you time, money, and stress – and turn your vacation into perfection.

Of course, your first inquiry is completely free – with no commitment whatsoever.

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