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By Huuk Team

Road trip from New York to Milwaukee

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Show more (3+)

ITINERARY

16h 49m886 miles17 stops
1
BrainXcape
160 Broadway 3rd Fl, New York City, NY 10038
2
The Blue Bar, Algonquin Hotel
59 W 44th St, New York City, NY 10036-6613
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
3
Hollywood Gaming Mahoning Valley Race Course
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
4
Paladin Brewing
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
5
Porthouse Theatre
Cleveland, OH 44242
6
F.A. Seiberling Nature Realm
1828 Smith Rd, Akron, OH 44313-5012
7
National Shrine of St Jude
3200 E 91st St, Chicago, IL 60617-4408
8
Promontory Point
5491 S Shore Dr, Chicago, IL 60615-5983
9
Spring Awakening Music Festival
6401 S Stony Island Ave Jackson Park, Chicago, IL 60637-3800
10
A. Philip Randolph Pullman Porter Museum
10406 S Maryland Ave Entrance 817 East 104th St from the parking lot, Chicago, IL 60628-3090
The National APR Pullman Porter Museum, is located in the National Park Service-Pullman National Monument. It is the only one of its kind world-wide. NAPRPPM is the first Black Labor History museum, in the United States, that exclusively tells the story of the Pullman Porters, The Brotherhood of Sleeping Car Porters labor union, and A. Philip Randolph Its founder. Tucked away on a quiet corner at the north end of Pullman National monument, don’t let the unassuming exterior keep you from missing this black heritage treasure. The museum presents, and interprets content intended to educate the public-on the impact the union had on organized labor, and on America’s modern day civil rights movement The exhibits chronicle the formation of the Brotherhood of Sleeping Car Porters; the first Black labor union in the United States chartered under the American Federation of Labor. Exhibits depict important activities on their amazing JOURNEY OF UNITY that ended in victory.
11
Soldier Field
1410 S Museum Campus Dr, Chicago, IL 60605-2902
Venerable home field of the Chicago Bears football team.
12
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
13
Boystown
Chicago, IL
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
14
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
15
South Shore Park
2900 S Shore Dr, Milwaukee, WI 53207-2542
Beautiful park on the lake shore. Great view of city in the distance. Nice place to play in the water or have a picnic.
16
The Riverside Theater
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
17
Klassic Limousine, Inc
1551 West Goldcrest Avenue, Milwaukee, WI 53221-5014
Thank you for choosing Klassic Limousine, Inc-your true North for the Wisconsin luxury transportation market. We are proud to be your first choice in Milwaukee, and we take your vote of confidence in us very seriously, and welcome you to VIP treatment on a larger scale. Based in Milwaukee, Klassic Limousine, Inc is all about luxury and elegance. As the undisputed leader in luxury we know how to deliver the VIP treatment the passenger expects. Founded with a desire to bring the best in luxury and modern class to our discerning clients, we are now the finest Milwaukee black car service. This is based on our commitment to being not only the best in urban transportation, but the best overall in terms of vehicle luxury and professionalism. With Klassic Limousine, Inc you travel your way. All of the above combined make us a superior Milwaukee limousine service. Therefore, when you choose Klassic Limousine, Inc you can rest assured that an unforgettable experience awaits you.
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OVERVIEW

Escape to the Midwest from the bustling streets of New York City, traversing over 800 miles to the vibrant shores of Lake Michigan. Immerse yourself in the heartland of America, where sprawling landscapes meet modern metropolises. This epic journey offers a captivating blend of urban and rural experiences, promising unforgettable moments at every turn.

Indulge in the unparalleled energy of the Big Apple, where towering skyscrapers cast long shadows over bustling avenues. Explore iconic landmarks, savor diverse culinary delights, and immerse yourself in the vibrant cultural tapestry. As you leave the urban jungle behind, prepare for a scenic transformation as lush greenery replaces towering buildings. Witness the rolling hills of Pennsylvania and Ohio, where picturesque towns and charming hamlets dot the countryside.

Finally, arrive in Milwaukee, a vibrant city on the shores of Lake Michigan. Discover a thriving arts and culture scene, explore historic neighborhoods, and indulge in the local culinary delights. Stroll along the scenic waterfront promenade, admiring the shimmering waters and breathtaking skyline views. This journey is not merely a transportation from one city to another; it's a transformative experience that showcases the rich diversity and captivating spirit of America's heartland.

1
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
2
The Blue Bar, Algonquin Hotel
New York City, New York·
4.0
(99) review
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
59 W 44th St, New York City, NY 10036-6613
3
Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
4
Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
5
Porthouse Theatre
Cleveland, Ohio·
5.0
(20) review
Cleveland, OH 44242
6
F.A. Seiberling Nature Realm
Akron, Ohio·
5.0
(203) review
1828 Smith Rd, Akron, OH 44313-5012
7
National Shrine of St Jude
Chicago, Illinois·
4.5
(7) review
3200 E 91st St, Chicago, IL 60617-4408
8
Promontory Point
Chicago, Illinois·
5.0
(9) review
5491 S Shore Dr, Chicago, IL 60615-5983
9
Spring Awakening Music Festival
Chicago, Illinois·
4.0
(8) review
6401 S Stony Island Ave Jackson Park, Chicago, IL 60637-3800
10
A. Philip Randolph Pullman Porter Museum
Chicago, Illinois·
3.5
(7) review
The National APR Pullman Porter Museum, is located in the National Park Service-Pullman National Monument. It is the only one of its kind world-wide. NAPRPPM is the first Black Labor History museum, in the United States, that exclusively tells the story of the Pullman Porters, The Brotherhood of Sleeping Car Porters labor union, and A. Philip Randolph Its founder. Tucked away on a quiet corner at the north end of Pullman National monument, don’t let the unassuming exterior keep you from missing this black heritage treasure. The museum presents, and interprets content intended to educate the public-on the impact the union had on organized labor, and on America’s modern day civil rights movement The exhibits chronicle the formation of the Brotherhood of Sleeping Car Porters; the first Black labor union in the United States chartered under the American Federation of Labor. Exhibits depict important activities on their amazing JOURNEY OF UNITY that ended in victory.
10406 S Maryland Ave Entrance 817 East 104th St from the parking lot, Chicago, IL 60628-3090
11
Soldier Field
Chicago, Illinois·
4.0
(935) review
Venerable home field of the Chicago Bears football team.
1410 S Museum Campus Dr, Chicago, IL 60605-2902
12
Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
333 Michigan Ave, Chicago, IL 60601-3901
13
Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
Chicago, IL
14
Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
1060 W. Addison St., Chicago, IL 60613-4566
15
South Shore Park
Milwaukee, Wisconsin·
5.0
(9) review
Beautiful park on the lake shore. Great view of city in the distance. Nice place to play in the water or have a picnic.
2900 S Shore Dr, Milwaukee, WI 53207-2542
16
The Riverside Theater
Milwaukee, Wisconsin·
4.0
(95) review
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
17
Klassic Limousine, Inc
Milwaukee, Wisconsin·
4.5
(9) review
Thank you for choosing Klassic Limousine, Inc-your true North for the Wisconsin luxury transportation market. We are proud to be your first choice in Milwaukee, and we take your vote of confidence in us very seriously, and welcome you to VIP treatment on a larger scale. Based in Milwaukee, Klassic Limousine, Inc is all about luxury and elegance. As the undisputed leader in luxury we know how to deliver the VIP treatment the passenger expects. Founded with a desire to bring the best in luxury and modern class to our discerning clients, we are now the finest Milwaukee black car service. This is based on our commitment to being not only the best in urban transportation, but the best overall in terms of vehicle luxury and professionalism. With Klassic Limousine, Inc you travel your way. All of the above combined make us a superior Milwaukee limousine service. Therefore, when you choose Klassic Limousine, Inc you can rest assured that an unforgettable experience awaits you.
1551 West Goldcrest Avenue, Milwaukee, WI 53221-5014

CHECKLIST

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Car charger and portable battery
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Water bottles and snacks
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Travel pillow and blanket
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Sunglasses and sunscreen
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First-aid kit
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Hand sanitizer and wet wipes
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Driver’s license and vehicle registration
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Cash and cards
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Camera or smartphone

HASHTAGS

#New York#Milwaukee#travel#transportation#distance#driving#flying#train#bus#road trip#vacation#weekend getaway#budget travel#family travel#solo travel#adventure travel#city break#weekend break#short break#long weekend#day trip#sightseeing#attractions#museums#monuments#landmarks#parks#beaches#shopping#nightlife#restaurants#bars#cafes#culture#history#architecture#art#music#theater#dance#film#fashion#design#photography#literature#food#drink#coffee#tea#chocolate#beer#wine#spirits#cocktails#nightlife#clubs#bars#pubs#lounges#live music#DJs#dancing#entertainment#events#festivals#holidays#parades#concerts#exhibitions#shows#performances#sports#games#competitions#tournaments#leagues#teams#players#athletes#coaches#fans#spectators#betting#gambling#odds#predictions#results#standings#statistics#injuries#transfers#rumors#news#analysis#commentary#opinion#editorials#features#interviews#profiles#biographies#history#trivia#facts#figures#data#statistics#records#achievements#awards#honors#recognition#accolades#praise#criticism#controversy#debate#discussion#analysis#commentary#opinion#editorials#features#interviews#profiles#biographies#history#trivia#facts#figures#data#statistics#records#achievements#awards#honors#recognition#accolades#praise#criticism#controversy#debate#discussion#analysis#commentary#opinion#editorials#features#interviews#profiles#biographies#history#trivia#facts#figures#data#statistics#records#achievements#awards#honors#recognition#accolades#praise#criticism#controversy#debate#discussion#analysis#commentary#opinion#editorials#features#interviews#profiles#biographies#history#trivia#facts#figures#data#statistics#records#achievements#awards#honors#recognition#accolades#praise#criticism#
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FAQ
Frequently Asked Questions
What's the driving distance between New York and Milwaukee?
The distance is 886 miles
What's the travel time between New York and Milwaukee?
The driving time can vary depending on traffic conditions, but it is typically 16h 49m mins in normal traffic
What are some of the best cities to visit between New York and Milwaukee?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Milwaukee?
There are plenty! Here are some stops you shouldn’t miss on your way to Milwaukee
What’s the weather like in Milwaukee?
The weather in Milwaukee is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Milwaukee in January
Weather in Milwaukee in February
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Interested in a detailed plan for your time in Milwaukee?
Plan your dream Milwaukee trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Milwaukee
A 2-day itinerary in Milwaukee
A 3-day itinerary in Milwaukee
A 4-day itinerary in Milwaukee
A 5-day itinerary in Milwaukee
A 6-day itinerary in Milwaukee
Where else can I travel to if I'm starting my trip in New York?
We have a lot of great trip options for New York! See the links below for all the itineraries we created for you