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Chicago Magic: Experience Taste, Festivity, and Ambience

Embark on a classic American road trip, exploring the cities of Chicago, Milwaukee, Detroit, and ending at Cleveland. Take a dive into the heart of the Midwest and experience the vibrant urban life, rich history, and unique cuisine each city has to offer.

Embark on a classic American road trip, exploring the cities of Chicago, Milwaukee, Detroit, and ending at Cleveland. Take a dive into the heart of the Midwest and experience the vibrant urban life, rich history, and unique cuisine each city has to offer.

Departure
Departure
Days

2

Nights

1

Chicago, Illinois is a bustling city known for its stunning architecture, diverse culinary scene, and incredible jazz music. It's home to several famous attractions, such as The Art Institute of Chicago, Navy Pier, and The Magnificent Mile. Grab a deep-dish pizza and cheer on the Cubs for a true Chicago experience.

Days

2

Nights

1

Milwaukee, a major city in Wisconsin, is known for its breweries and its rich history of industry and immigrants. Its lakefront skyline is dotted with a mix of architectural styles. The city is also known for its beautiful parks, bike trails, and music festivals.

Days

2

Nights

1

Detroit, Michigan, is coined as 'The Motor City' due to its rich automotive history. Boasting cultural attractions like the Detroit Institute of Arts and historical landmarks like the Henry Ford Museum. Detroit is a city of renaissance, with a vibrant arts scene and eateries gaining national attention.

Days

2

Nights

1

Cleveland, in Ohio, is a major city on the banks of Lake Erie. Known for its vibrant music scene, it's home to the Rock and Roll Hall of Fame. The city's downtown area is revitalized and features modern attractions like the Playhouse Square theatre district and the Cleveland Aquarium.

Days

2

Night

1

Arrival
Arrival
Suggested Locations

United States

Suggested Locations

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Visit Art Institute of Chicago

My Places

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Explore Navy Pier

My Places

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Try Chicago-Style Deep-Dish Pizza

My Places

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Washington

Day 1

Air Drive

819 km

Chicago

Day 1

9:00 AM

10:08 AM

1h 8m

Estimate time

Plane
Chicago

Day 2

Air Drive

128 km

Milwaukee

Day 2

9:00 AM

10:19 AM

1h 19m

Plane
Milwaukee

Day 3

Air Drive

403 km

Detroit

Day 3

9:00 AM

9:33 AM

1h 33m

Estimate time

Plane
Detroit

Day 4

Air Drive

261 km

Cleveland

Day 4

9:00 AM

11:47 AM

3h 47m

Plane
Cleveland

Day 5

Air Drive

1,302 km

Washington

Day 5

9:00 AM

10:48 AM

2h 48m

Estimate time

Plane

Calender data is not found.

CityCenter
Activities

TripPilot

Travel Tips

Sure! Here's some information for your planned road trip from Chicago to Milwaukee, Detroit, and Cleveland:

Best Time to Visit:
The ideal time to visit these cities is during the late spring, summer, and early fall (May through October). During this time, the temperatures are warm and numerous events are taking place.

Route and Accessibility:
You can start your trip in Chicago, then head north to Milwaukee (around 1.5 hours drive via I-94 W). From Milwaukee, Detroit is a 6-hour drive east (via I-94 E). Finally, from Detroit, you would head south-east to reach Cleveland, which is a 3-hour drive (via I-90 E).

Altitude and Acclimatization:
These cities are all close to sea level, so you won't have issues with altitude sickness.

Accommodation and Booking:
Book accommodations in advance, there is a wide range of options in all four cities from luxury hotels to budget-friendly lodgings.

Clothing and Essentials:
Pack according to the season in which you are visiting. Summer can get hot so pack light clothing, but always take a couple of jackets or sweaters as it can get cool in the evenings. Comfortable walking shoes are a must as these cities have lots of attractions to walk around. If you'll be near Lake Michigan or Lake Erie, you might want to pack a swimsuit as well.

Health and Safety:
Always have a plan for emergencies and keep your health insurance information handy. Follow traffic laws and always have a designated driver if drinking.

Local Etiquette and Respect:
Local customs in these cities are quite typical of the United States. Be polite, tip 15-20% in restaurants, and respect any local customs or rules in each city. Be sure to show respect to local cultures and traditions, as these cities have diverse populations with different backgrounds.