Road trip from New York to Chicago
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Museums
Shopping
Nature & Parks
Concerts & Shows
Sights & Landmarks
Fun & Games
Nightlife
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All Category
Museums
Shopping
Nature & Parks
Concerts & Shows
Sights & Landmarks
Fun & Games
Nightlife
Food & Drink
Casinos & Gambling
Classes & Workshops
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ITINERARY
15h 0m795 miles26 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
Mack Trucks Historical Museum
7
Allentown Rose Gardens
8
Haines Mill Museum
9
Josh Early Candies
10
Marine Corps League NE Detachment Museum
11
Everhart Museum
12
Steamtown National Historic Site
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
13
Basilica of Our Lady of Mount Carmel
14
OH WOW! The Roger & Gloria Jones Children's Center for Science & Technology
OH WOW!TM’s colorful, hands-on environment encourages independent thinking through interactive STEM-based exhibits and EDUtaining programs.”
15
Hollywood Gaming Mahoning Valley Race Course
16
Paladin Brewing
17
Lock 3
18
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
19
Sprucewood Shores Estate Winery
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
20
Lakeside Park & Rose Garden
21
Allen County War Memorial Coliseum
22
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
23
The Chopping Block
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
24
Boystown
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
25
Wrigley Field
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.
26
What Lifts You Mural
You can find one of the town’s most famous photo ops in The Gulch neighborhood—a pair of intricate white lace wings against a black wall. There's usually a line, so go early in the morning or late in the day for fewer crowds. Try to find the easter eggs that the artist put into the mural: a cowboy hat, guitars, and barbecues to represent Nashville. Explore other street art in Nashville on a mural art tour—you'll see lots of other great sights, with plenty of time for photo ops.
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:Mack Trucks Historical Museum
Allentown, Pennsylvania·
4.5
(95) review
2402 Lehigh Pkwy S, Allentown, PA 18103-2900
7
Start:Allentown Rose Gardens
Allentown, Pennsylvania·
4.5
(78) review
3000 Parkway Blvd, Allentown, PA 18104-5327
8
Start:Haines Mill Museum
Allentown, Pennsylvania·
4.5
(7) review
3600 Dorney Park Rd Cetronia, Allentown, PA 18104-5845
9
Start:Josh Early Candies
Allentown, Pennsylvania·
4.5
(74) review
4640 W Tilghman St, Allentown, PA 18104-3293
10
Start:Marine Corps League NE Detachment Museum
Scranton, Pennsylvania·
5.0
(8) review
1340 Alder Street, Scranton, PA
11
Start:Everhart Museum
Scranton, Pennsylvania·
4.0
(76) review
1901 Mulberry St, Scranton, PA 18510-2390
12
Start:Steamtown National Historic Site
Scranton, Pennsylvania·
4.5
(902) review
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
13
Start:Basilica of Our Lady of Mount Carmel
Youngstown, Ohio·
4.5
(7) review
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
14
Start:OH WOW! The Roger & Gloria Jones Children's Center for Science & Technology
Youngstown, Ohio·
4.5
(62) review
OH WOW!TM’s colorful, hands-on environment encourages independent thinking through interactive STEM-based exhibits and EDUtaining programs.”
15
Start:Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
16
Start:Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
17
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
18
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
19
Start:Sprucewood Shores Estate Winery
Harrow, Essex, Ontario·
4.5
(97) review
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
20
Start:Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
21
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
22
Start: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.
23
Start:The Chopping Block
Chicago, Illinois·
4.5
(98) review
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
24
Start: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
25
Start: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.
26
Start:What Lifts You Mural
Nashville, Davidson County, Tennessee·
4.5
(83) review
You can find one of the town’s most famous photo ops in The Gulch neighborhood—a pair of intricate white lace wings against a black wall. There's usually a line, so go early in the morning or late in the day for fewer crowds. Try to find the easter eggs that the artist put into the mural: a cowboy hat, guitars, and barbecues to represent Nashville. Explore other street art in Nashville on a mural art tour—you'll see lots of other great sights, with plenty of time for photo ops.
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 0m 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