logo
By Huuk Team

Road trip from New York to Chicago

All Category
iconNature & Parks
iconMuseums
iconFun & Games
iconConcerts & Shows
iconNightlife
iconSights & Landmarks
iconShopping
Show more (1+)

ITINERARY

15h 1m795 miles17 stops
1
BrainXcape
160 Broadway 3rd Fl, New York City, NY 10038
2
Daniel Roy's Parlour Of Deceptions
47 5th Avenue, New York City, NY 10003
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.
3
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.
4
Precision NY Chauffeur & Airport Transportation Services
1177 Avenue Of Americas 5th Floor, New York City, NY 10036
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.
5
Duke Island Park
Old York Road, Bridgewater, NJ
6
Twin Rivers Tubing
1 Centre Square, Easton, PA 18042
New for 2022 are Cooler Tubes for carrying coolers and personal gear. WE MOVED to EASTON PA from Phillipsburg NJ in 2021. Going on our 9th season. Best in Class Facilities - Over Looking The River Falls It is a breathtaking setting located in Easton, PA overlooking the state of New Jersey. This is where the Lehigh River & Delaware River merge. You and your loved ones will be energized for the fun 2-3 hour water journey ahead of you! We offer Regular, Extra Large and Backrest tubes with cup holders and Cooler tubes. Tube tethers are free for complete connected fun! Facilities include indoor changing rooms and rest rooms. Our ratings speak to our ability to go above & beyond in customer service! We accommodate the single tuber to the largest corporate outing, camp groups, church groups, bachelor/bachorlette parties, fundraisers and of course simple family fun! After tubing there are plenty of places to eat and drink in Downtown Easton all in 5 minute walking distance. We are the only t
7
Mack Trucks Historical Museum
2402 Lehigh Pkwy S, Allentown, PA 18103-2900
8
Lehigh Gorge Scenic Railway
1 Susquehanna Street, Jim Thorpe, PA 18229-3735
Lehigh Gorge trains, a trademark of the Reading and Northern Railroad, take a 70 minute round-trip tour following the Lehigh River over bridges, through Glen Onoko, into the Lehigh Gorge State Park. High-rising cliffs and mountain scenery surround the train along the route to Old Penn Haven. You will see hikers, rafters, mountain bikers, and wildlife along the railroad. You will learn about railroad lore, wildlife, the history of the anthracite coal region, and the people who launched America into the Industrial Age. Seasonal days and hours apply throughout the year. Call for more information or visit our website for current schedules.
9
Gorge Metro Park
1160 Front St., Cuyahoga Falls, OH
10
Lock 3
200 S Main St, Akron, OH 44308-1315
11
Federal Reserve Bank of Cleveland: Education and Learning Center
1455 E 6th St, Cleveland, OH 44114-2517
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.
12
Rock & Roll Hall of Fame
1100 Rock and Roll Blvd Main Terminal, Cleveland, OH 44114-1023
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
13
SouthPark Mall
500 Southpark Ctr, Strongsville, OH 44136-9320
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.
14
Old Lighthouse Museum
100 Heisman Harbor Road, Michigan City, IN 46360
Explore the history of Michigan City and its relationship to Lake Michigan. Learn about lighthouses and their keepers, the harbor, shipwrecks and Indiana's lakeshore.
15
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.
16
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
17
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.
Customize this Trip

OVERVIEW

New York to Chicago
1
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
2
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.
47 5th Avenue, New York City, NY 10003
3
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
4
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.
1177 Avenue Of Americas 5th Floor, New York City, NY 10036
5
Duke Island Park
Bridgewater, New Jersey·
4.5
(99) review
Old York Road, Bridgewater, NJ
6
Twin Rivers Tubing
Easton, Pennsylvania·
4.5
(92) review
New for 2022 are Cooler Tubes for carrying coolers and personal gear. WE MOVED to EASTON PA from Phillipsburg NJ in 2021. Going on our 9th season. Best in Class Facilities - Over Looking The River Falls It is a breathtaking setting located in Easton, PA overlooking the state of New Jersey. This is where the Lehigh River & Delaware River merge. You and your loved ones will be energized for the fun 2-3 hour water journey ahead of you! We offer Regular, Extra Large and Backrest tubes with cup holders and Cooler tubes. Tube tethers are free for complete connected fun! Facilities include indoor changing rooms and rest rooms. Our ratings speak to our ability to go above & beyond in customer service! We accommodate the single tuber to the largest corporate outing, camp groups, church groups, bachelor/bachorlette parties, fundraisers and of course simple family fun! After tubing there are plenty of places to eat and drink in Downtown Easton all in 5 minute walking distance. We are the only t
1 Centre Square, Easton, PA 18042
7
Mack Trucks Historical Museum
Allentown, Pennsylvania·
4.5
(95) review
2402 Lehigh Pkwy S, Allentown, PA 18103-2900
8
Lehigh Gorge Scenic Railway
Jim Thorpe, Pocono Mountains Region, Pennsylvania·
4.0
(955) review
Lehigh Gorge trains, a trademark of the Reading and Northern Railroad, take a 70 minute round-trip tour following the Lehigh River over bridges, through Glen Onoko, into the Lehigh Gorge State Park. High-rising cliffs and mountain scenery surround the train along the route to Old Penn Haven. You will see hikers, rafters, mountain bikers, and wildlife along the railroad. You will learn about railroad lore, wildlife, the history of the anthracite coal region, and the people who launched America into the Industrial Age. Seasonal days and hours apply throughout the year. Call for more information or visit our website for current schedules.
1 Susquehanna Street, Jim Thorpe, PA 18229-3735
9
Gorge Metro Park
Cuyahoga Falls, Ohio·
4.5
(99) review
1160 Front St., Cuyahoga Falls, OH
10
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
11
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.
1455 E 6th St, Cleveland, OH 44114-2517
12
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
1100 Rock and Roll Blvd Main Terminal, Cleveland, OH 44114-1023
13
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.
500 Southpark Ctr, Strongsville, OH 44136-9320
14
Old Lighthouse Museum
Michigan City, Indiana·
4.5
(99) review
Explore the history of Michigan City and its relationship to Lake Michigan. Learn about lighthouses and their keepers, the harbor, shipwrecks and Indiana's lakeshore.
100 Heisman Harbor Road, Michigan City, IN 46360
15
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
16
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
17
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

CHECKLIST

icon
GPS device or app
icon
Download Offline Map
icon
Car charger and portable battery
icon
Water bottles and snacks
icon
Travel pillow and blanket
icon
Sunglasses and sunscreen
icon
First-aid kit
icon
Trash bags
icon
Hand sanitizer and wet wipes
icon
Driver’s license and vehicle registration
icon
Cash and cards
icon
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
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
Weather in Chicago in February
Weather in Chicago in March
Weather in Chicago in April
Weather in Chicago in May
Weather in Chicago in June
Weather in Chicago in July
Weather in Chicago in August
Weather in Chicago in September
Weather in Chicago in October
Weather in Chicago in November
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!
A 1-day itinerary in Chicago
A 2-day itinerary in Chicago
A 3-day itinerary in Chicago
A 4-day itinerary in Chicago
A 5-day itinerary in Chicago
A 6-day itinerary in Chicago
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