Road trip from Trenton to Chicago
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Museums
Concerts & Shows
Classes & Workshops
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ITINERARY
14h 20m779 miles29 stops
1
Philadelphia Distilling
2
Dave & Buster's - Arcade
At Dave & Buster's you can play hundreds of the hottest new arcade games in our Million Dollar Midway and win tickets for epic prizes. Try our mouth-watering, chef-crafted creations in our American restaurant. From wings to steaks, we've got whatever suits your appetite. Our premium sports bar features innovative cocktails, impressive wine selection, and 20+ beers to assure we're stocked to satisfy! Watch your team on one of our massive HDTVs with epic stadium sound that surrounds you from every direction in the sports bar that crushes the competition. Invite all your friends or coworkers for an unforgettable party or event! We work with every size and budget to make planning easy so you can focus on the FUN!
3
Christ Church
This church's congregation has included Ben Franklin, George Washington and Betsy Ross.
4
Old City Hall
5
Logan Circle
6
Cathedral Basilica of Saints Peter and Paul
The head church of Philadelphia's Catholic Archdiocese is on the National Registrar of Historic Places. Pope John Paul II celebrated Mass here in 1979.
7
John Heinz National Wildlife Refuge at Tinicum
Visit John Heinz National Wildlife Refuge at Tinicum! Come enjoy 10 miles of walking trails through wooded forests, an impoundment pond, and 300 acres of the largest remaining freshwater tidal marsh in PA. Visitors can also experience the marsh on the water through 4.5 mile of Darby Creek by canoe or kayak. Stop by the front desk to borrow binoculars or fishing rods. Refuge trails are open every day from sunrise to sunset, free of charge. The Visitor Center is open daily from 8:30 AM to 4:00 PM. The visitor center building is closed for all Federal holidays however the trails remain open. Darby Creek is tidal and navigable only within 2 hours before and after high tide. Boat Launch is located at the trailhead of Dike Trail. Visitors must provide their own canoe/kayak and life vests. John Heinz NWR offers year-round free recreational and educational programs.
8
Pennsylvania State Capitol
Teddy Roosevelt declared that this Italian Renaissance-style building was the handsomest building I ever saw. Indeed, the State Capitol, with its vaulted dome and grand staircase and the murals and painted floors inside, is thing to behold.
9
Cathedral of Learning
10
Allegheny Cemetery
Instituted in 1844, this 300-acre cemetery is the final resting place of such notables as Lillian Russell, Stephen Foster and General John Neville.
11
Mix Candle Co
12
Pittsburgh Water Steps
13
Point State Park
Serving as a key strategic spot during the French and Indian War, this National Historic Landmark and park offer stunning views of the city and a variety of outdoor recreation.
14
Allegheny Observatory
15
Lock 3
16
Museum of Contemporary Art Cleveland
17
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.
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
Fish Point Nature Reserve
20
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)
21
Lakeside Park & Rose Garden
22
Allen County War Memorial Coliseum
23
Soldier Field
Venerable home field of the Chicago Bears football team.
24
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
25
The 900 Shops Mall
26
Museum Of Illusions Chicago
27
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.
28
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
29
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.
Customize this Trip
OVERVIEW
Trenton to Chicago
1
Start:Philadelphia Distilling
Philadelphia, Pennsylvania·
5.0
(98) review
25 E Allen St, Philadelphia, PA 19123-1753
2
Start:Dave & Buster's - Arcade
Philadelphia, Pennsylvania·
3.0
(98) review
At Dave & Buster's you can play hundreds of the hottest new arcade games in our Million Dollar Midway and win tickets for epic prizes. Try our mouth-watering, chef-crafted creations in our American restaurant. From wings to steaks, we've got whatever suits your appetite. Our premium sports bar features innovative cocktails, impressive wine selection, and 20+ beers to assure we're stocked to satisfy! Watch your team on one of our massive HDTVs with epic stadium sound that surrounds you from every direction in the sports bar that crushes the competition. Invite all your friends or coworkers for an unforgettable party or event! We work with every size and budget to make planning easy so you can focus on the FUN!
3
Start:Christ Church
Philadelphia, Pennsylvania·
4.5
(970) review
This church's congregation has included Ben Franklin, George Washington and Betsy Ross.
4
Start:Old City Hall
Philadelphia, Pennsylvania·
4.5
(99) review
Independence Mall, Philadelphia, PA 19106
5
Start:Logan Circle
Philadelphia, Pennsylvania·
4.0
(97) review
Benjamin Franklin Parkway at 19th Street, Philadelphia, PA 19103
6
Start:Cathedral Basilica of Saints Peter and Paul
Philadelphia, Pennsylvania·
4.5
(978) review
The head church of Philadelphia's Catholic Archdiocese is on the National Registrar of Historic Places. Pope John Paul II celebrated Mass here in 1979.
7
Start:John Heinz National Wildlife Refuge at Tinicum
Philadelphia, Pennsylvania·
4.5
(93) review
Visit John Heinz National Wildlife Refuge at Tinicum! Come enjoy 10 miles of walking trails through wooded forests, an impoundment pond, and 300 acres of the largest remaining freshwater tidal marsh in PA. Visitors can also experience the marsh on the water through 4.5 mile of Darby Creek by canoe or kayak. Stop by the front desk to borrow binoculars or fishing rods. Refuge trails are open every day from sunrise to sunset, free of charge. The Visitor Center is open daily from 8:30 AM to 4:00 PM. The visitor center building is closed for all Federal holidays however the trails remain open. Darby Creek is tidal and navigable only within 2 hours before and after high tide. Boat Launch is located at the trailhead of Dike Trail. Visitors must provide their own canoe/kayak and life vests. John Heinz NWR offers year-round free recreational and educational programs.
8
Start:Pennsylvania State Capitol
Harrisburg, Pennsylvania·
4.5
(977) review
Teddy Roosevelt declared that this Italian Renaissance-style building was the handsomest building I ever saw. Indeed, the State Capitol, with its vaulted dome and grand staircase and the murals and painted floors inside, is thing to behold.
9
Start:Cathedral of Learning
Pittsburgh, Pennsylvania·
4.5
(979) review
4200 5th Ave., Pittsburgh, PA 15260
10
Start:Allegheny Cemetery
Pittsburgh, Pennsylvania·
4.5
(94) review
Instituted in 1844, this 300-acre cemetery is the final resting place of such notables as Lillian Russell, Stephen Foster and General John Neville.
11
Start:Mix Candle Co
Pittsburgh, Pennsylvania·
5.0
(9) review
4409 Butler St, Pittsburgh, PA 15201-3011
12
Start:Pittsburgh Water Steps
Pittsburgh, Pennsylvania·
4.5
(94) review
North Shore Riverfront Park, Pittsburgh, PA 15212
13
Start:Point State Park
Pittsburgh, Pennsylvania·
4.5
(951) review
Serving as a key strategic spot during the French and Indian War, this National Historic Landmark and park offer stunning views of the city and a variety of outdoor recreation.
14
Start:Allegheny Observatory
Pittsburgh, Pennsylvania·
5.0
(9) review
159 Riverview Ave Riverview Park, Pittsburgh, PA 15214-2299
15
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
16
Start:Museum of Contemporary Art Cleveland
Cleveland, Ohio·
3.5
(93) review
11400 Euclid Ave, Cleveland, OH 44106-3926
17
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.
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:Fish Point Nature Reserve
Pelee Island, Ontario·
4.5
(92) review
McCormick Rd, Ontario N0R 1M0 Canada
20
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)
21
Start:Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
22
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
23
Start:Soldier Field
Chicago, Illinois·
4.0
(935) review
Venerable home field of the Chicago Bears football team.
24
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.
25
Start:The 900 Shops Mall
Chicago, Illinois·
4.0
(96) review
900 N Michigan Ave, Chicago, IL 60611-1542
26
Start:Museum Of Illusions Chicago
Chicago, Illinois·
4.5
(97) review
25 E Washington St, Chicago, IL 60602-1708
27
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.
28
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
29
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.
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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FAQ
Frequently Asked Questions
What's the driving distance between Trenton and Chicago?
The distance is 779 miles
What's the travel time between Trenton and Chicago?
The driving time can vary depending on traffic conditions, but it is typically 14h 20m mins in normal traffic
What are some of the best cities to visit between Trenton 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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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 Trenton?
We have a lot of great trip options for Trenton! See the links below for all the itineraries we created for you