Road trip from New York to Chicago
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Concerts & Shows
Fun & Games
Shopping
Nightlife
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Museums
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All Category
Concerts & Shows
Fun & Games
Shopping
Nightlife
Spas & Wellness
Classes & Workshops
Museums
Nature & Parks
Outdoor Activities
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ITINERARY
15h 1m795 miles25 stops
1
Accomplice New York
This comedic interactive experience sends you on a mission to assist a bunch of ex-cons lookin’ to skip town. The journey starts near the South Street Seaport and works its way up through some of New York City's most colorful neighborhoods. Several alcoholic beverages and light appetizers are included during this three hour journey. For private groups, you can book up to 15 people. Basic pricing per person is $85.00. Accomplice also runs a Village show, a Chelsea show and a traveling meal, each with its own characters and story line. For more information, please visit our website!
2
BrainXcape
3
Daniel Roy's Parlour Of Deceptions
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
4
The Blue Bar, Algonquin Hotel
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
5
Precision NY Chauffeur & Airport Transportation Services
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
6
Chelsea Market
Chelsea Market is a world-famous food hall in the heart of New York City's Meatpacking District. Commonly featured in walking and food tours, the market has an array of dining options that draw both locals and travelers. Set aside a couple of hours to conquer the corridors of this sprawling indoor marketplace. Many travelers load up on fresh produce, prime cuts of meat, artisanal cheeses, and even imported Italian dry goods. For more elbow room, visit either early in the morning or late in the afternoon. Plus, keep a lookout for delicious free samples and the quaint bookstore on site. – Tripadvisor
7
The Urban Muse
8
Brushes & Bisque
9
Lake Hopatcong Adventure Company
We offer guided tours around the Lake Hopatcong area. Our equipment includes Hydrobikes , Hobie Mirage Eclipse Pedalboards for our lake adventures and your hiking boots for our woodland explorations.
10
Frank Frazetta Museum
11
Skylanes Bowling Center
12
Big Pocono State Park
13
Mount Airy Casino
14
Gorge Metro Park
15
Museum of Contemporary Art Cleveland
16
Federal Reserve Bank of Cleveland: Education and Learning Center
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
17
Rock & Roll Hall of Fame
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
18
SouthPark Mall
For shopping near Cleveland, the SouthPark Mall is a favored destination. The mall hosts Dillard's and Macy's department stores, over 175 restaurants and shops and a Cinemark movie theater in Strongsville, OH. Find the shopping center at Royalton and Howe, just west of I-71.
19
Great Northern Mall
Great Northern Mall near Cleveland hosts shopping, Macy's and JCPenney department stores, Dick's Sporting Goods store, and over 120 more shops and restaurants. The mall is twelve miles southwest of Cleveland on I-480. Find convenient family parking near the H&M and Dillard's mall entrances.
20
Zollner Golf Course
21
Elkhart Environmental Center
22
The Lerner Theatre
23
O'Rourke's Public House
24
Corby's Irish Pub
25
Brincka Cross Gardens
Customize this Trip
OVERVIEW
New York to Chicago
1
Start:Accomplice New York
New York City, New York·
4.5
(987) review
This comedic interactive experience sends you on a mission to assist a bunch of ex-cons lookin’ to skip town. The journey starts near the South Street Seaport and works its way up through some of New York City's most colorful neighborhoods. Several alcoholic beverages and light appetizers are included during this three hour journey. For private groups, you can book up to 15 people. Basic pricing per person is $85.00. Accomplice also runs a Village show, a Chelsea show and a traveling meal, each with its own characters and story line. For more information, please visit our website!
2
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
3
Start:Daniel Roy's Parlour Of Deceptions
New York City, New York·
5.0
(99) review
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
4
Start: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.
5
Start:Precision NY Chauffeur & Airport Transportation Services
New York City, New York·
5.0
(99) review
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
6
Start:Chelsea Market
New York City, New York·
4.5
(9849) review
Chelsea Market is a world-famous food hall in the heart of New York City's Meatpacking District. Commonly featured in walking and food tours, the market has an array of dining options that draw both locals and travelers. Set aside a couple of hours to conquer the corridors of this sprawling indoor marketplace. Many travelers load up on fresh produce, prime cuts of meat, artisanal cheeses, and even imported Italian dry goods. For more elbow room, visit either early in the morning or late in the afternoon. Plus, keep a lookout for delicious free samples and the quaint bookstore on site. – Tripadvisor
7
Start:The Urban Muse
Denville, Morris County, New Jersey·
5.0
(9) review
82 Broadway, Denville, NJ 07834-2763
8
Start:Brushes & Bisque
Denville, Morris County, New Jersey·
4.5
(8) review
45 Broadway, Denville, NJ 07834-2767
9
Start:Lake Hopatcong Adventure Company
Lake Hopatcong, New Jersey·
5.0
(8) review
We offer guided tours around the Lake Hopatcong area. Our equipment includes Hydrobikes , Hobie Mirage Eclipse Pedalboards for our lake adventures and your hiking boots for our woodland explorations.
10
Start:Frank Frazetta Museum
East Stroudsburg, Pocono Mountains Region, Pennsylvania·
5.0
(9) review
141 Museum Road, East Stroudsburg, PA 18301
11
Start:Skylanes Bowling Center
East Stroudsburg, Pocono Mountains Region, Pennsylvania·
4.0
(9) review
100 Eagle Valley Mall, East Stroudsburg, PA 18301
12
Start:Big Pocono State Park
Tannersville, Pocono Mountains Region, Pennsylvania·
4.5
(91) review
980 Camelback Rd, Tannersville, PA 18372
13
Start:Mount Airy Casino
Mount Pocono, Pocono Mountains Region, Pennsylvania·
3.5
(930) review
312 Woodland Rd, Mount Pocono, PA 18344-7172
14
Start:Gorge Metro Park
Cuyahoga Falls, Ohio·
4.5
(99) review
1160 Front St., Cuyahoga Falls, OH
15
Start:Museum of Contemporary Art Cleveland
Cleveland, Ohio·
3.5
(93) review
11400 Euclid Ave, Cleveland, OH 44106-3926
16
Start:Federal Reserve Bank of Cleveland: Education and Learning Center
Cleveland, Ohio·
4.5
(95) review
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
17
Start:Rock & Roll Hall of Fame
Cleveland, Ohio·
4.5
(9964) review
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
18
Start:SouthPark Mall
Strongsville, Ohio·
4.0
(94) review
For shopping near Cleveland, the SouthPark Mall is a favored destination. The mall hosts Dillard's and Macy's department stores, over 175 restaurants and shops and a Cinemark movie theater in Strongsville, OH. Find the shopping center at Royalton and Howe, just west of I-71.
19
Start:Great Northern Mall
North Olmsted, Ohio·
4.0
(93) review
Great Northern Mall near Cleveland hosts shopping, Macy's and JCPenney department stores, Dick's Sporting Goods store, and over 120 more shops and restaurants. The mall is twelve miles southwest of Cleveland on I-480. Find convenient family parking near the H&M and Dillard's mall entrances.
20
Start:Zollner Golf Course
Angola, Indiana·
4.0
(9) review
1215 Park Avenue, Angola, IN 46703
21
Start:Elkhart Environmental Center
Elkhart, Indiana·
4.5
(9) review
1717 E Lusher Ave, Elkhart, IN 46516-4967
22
Start:The Lerner Theatre
Elkhart, Indiana·
5.0
(95) review
410 South Main Street, Elkhart, IN 46516
23
Start:O'Rourke's Public House
South Bend, Indiana·
4.5
(9) review
1044 E Angela Blvd, South Bend, IN 46617-1374
24
Start:Corby's Irish Pub
South Bend, Indiana·
3.5
(9) review
441 E Lasalle Ave, South Bend, IN 46617-2723
25
Start:Brincka Cross Gardens
Michigan City, Indiana·
4.0
(9) review
427 E Furness Rd, Michigan City, IN 46360-9535
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
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EXPLORE MORE
Discover Exciting Road Trip Inspirations
New York to Chicago
795 miles
15h 0m
26 stops
MuseumsShoppingNature & ParksConcerts & ShowsSights & Landmarks
New York to Chicago
795 miles
15h 0m
26 stops
MuseumsShoppingNature & ParksConcerts & ShowsSights & Landmarks
New York to Chicago
795 miles
15h 0m
26 stops
MuseumsShoppingNature & ParksConcerts & ShowsSights & Landmarks
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FAQ
Frequently Asked Questions
What's the driving distance between New York and Chicago?
The distance is 795 miles
What's the travel time between New York and Chicago?
The driving time can vary depending on traffic conditions, but it is typically 15h 1m mins in normal traffic
What are some of the best cities to visit between New York and Chicago?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chicago?
There are plenty! Here are some stops you shouldn’t miss on your way to Chicago
What’s the weather like in Chicago?
The weather in Chicago is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Chicago in January
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Weather in Chicago in December
Interested in a detailed plan for your time in Chicago?
Plan your dream Chicago trip with our daily itineraries featuring must-see attractions! See them here!
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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