Road Trip

5 min read

Unlock Chicago's Secrets: Epic Road Trips & Maps Guide

Buckle up, adventurers! Forget the beaten path—our interactive maps will steer you to Chicago's best-kept secrets. Get ready to gear up for the road trip of a lifetime!

Tobi Miles
January 26, 2020

The Windy City, Chicago, Illinois is a large metropolis on the scenic Lake Michigan. The Skyline is punctuated with vast skyscrapers, such as the Willis Tower (Former Sears Tower) and the Legendary John Hancock Center at over 1,451ft high.

Chicago is also known for its tasty foods from Chicago style pizza (Deep dish) & mouth watering Chicago hot dogs. In addition, Chicago is know for its Jazz and of course the Notorious 1920s gangster Al Capone!

In this post i'm going to run through my top 4 most life changing road trips I've taken to or from Chicago! I've also included an interactive road trip map for each & Itinerary! So lets Dive right in!

4. New York City to Chicago Road Trip!

New York City and Chicago have always had a rivalry. Some say New York is just Bigger & Badder, while others point out that the Chicago people are just more friendly & laid back!

Me & my girlfriend were having this same dispute…so to settle any arguments we decided to to a road trip between New York City & Chicago and of course head past some great cities on the way!

New York TO Chicago Road Trip

New York City to Chicago Road Trip Itinerary:

  1. New York City
  2. Philadelphia
  3. Baltimore
  4. Washington D.C
  5. Pittsburgh
  6. Cleveland
  7. Detroit
  8. Chicago

You can also head to Chicago via Finger Lakes & Niagara Falls which is a great option!

See: New York City to Niagara falls Road trip!

Interactive Map (New York to Chicago Road Trip):

Dive into our Interactive map below!

User Guide:  Simply Click the +/- buttons to zoom in & out,  Click on a favourite attraction, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to share our map on facebook by clicking the link below:


Webmasters: Why not embed this map on your website to help your readers? Feel free by clicking the link in the top right corner.

But remember to credit us at:

How far is Chicago from New York?

There are 795 miles between New York & Chicago. Driving direct it would take you 13hr, 7 mins...but where is the fun in that!

Road Trips are about the journey and the amazing places to stop along the way!

Related Read: Best Time to Visit Chicago

Is it cheaper to fly or drive?

It’s not always cheaper to drive, but in many cases it be less than half the cost of flying to drive and alot more fun!

new york road trip hammock girl

Which is the best method of transport from New York to Chicago?

From the Table below we evaluated which is the best method of transport between New York and Chicago. Now this all depends on personal preference.

However, from the data it’s clear that the Bus is the cheapest method of transport between New York and Chicago.

So if your a real Backpacker and don’t want to rent a car then this is a great option for you. However, there are a couple of negatives against taking the Bus.

There is not as much comfort and space as the train and you can’t stop off as many times as you could in a car!

For more on Public transport to Chicago check out: New York to Chicago on Public Transport: Is it worth it?

Dive into our helpful comparison table below!

Should I take the train between New York & Chicago?

The Amtrak train takes you up through Connecticut, Massachusetts before traveling along the coast of New York state.

This is a really Scenic train ride and an experience in itself. For more info see: Ultimate Guide to the USA by Amtrak Trains

Buffalo New York train journey

For our full New York to Chicago Road Trip Itinerary

check out:New York City to Chicago Road Trip: Itinerary/Map

3. Chicago to Iowa: wild west road trip!

A Chicago to Iowa Road Trip is a short but sweet mid america road trip! Along the way you will drive through authentic Americana.  Line of sight you can travel the 236 miles  between Chicago & Iowa in approximately 4 hours! However, we prefer to take the more scenic route to really experience old americana.

freight-house-farmers market. Iowa.

Chicago to Iowa Road Trip Itinerary

Here are our Stops along the way.

  1. Chicago
  2. Naperville
  3. Rockford
  4. Galena
  5. Dubuque
  6. Davenport
  7. Iowa City, Iowa
  8. Bonus: Amana Colonies

Interactive map (New York to Chicago Road Trip):

Dive into our Interactive Map below, for the best attractions to see on a road trip between Chicago & Iowa.

User Guide:  Simply Click the +/- buttons to zoom in & out, (Zoom out to see Blowing rock).

Click on a favourite restaurant, and click directions symbol to give you the driving or walking route directly there!

(Many visitors choose to share our map on facebook by clicking the link below!)


Be sure to visit Galena!

Galena is a historic small town in northwest Illinois. This little town down is old school Americana at its best! Here you will find a host of 19th century buildings such as the 1826 Dowling House and Hourseshoe Mount which offers views of THREE STATES!

You can check out other ancient ceremonial sites at Casper Bluff.

Things to do in Galena:

  • Home of Ulysses S Grant
  • Chicago Atheneum
  • The Dowling House
  • Galena Grant Park
  • Galena Ghost Tours.
  • Galena Trolley Tours

For the full Itinerary be sure to check out this post here: Chicago to Iowa Road Trip: Wicked Mid West!

2. Atlanta to Chicago Road Trip

Atlanta is known for it’s southern hospitality, diverse musical heritage and number of world records!

It also has the busiest passenger airport in the United States of America the Harts-field Jackson Atlanta International Airport, which draws over 50 million people annually!

This makes it a popular starting point for many great US road trips!

Atlanta to Chicago Road Trip Itinerary:

  1. Atlanta, Georgia
  2. Chattanooga, TN
  3. Nashville, TN
  4. Louisville, Kentucky
  5. Indianapolis, Indiana
  6. Chicago, Illinois

Interactive map (Atlanta to Chicago Road Trip)

Dive into our interactive Map below!

User Guide: Use the +/- arrows to zoom in an out of the landmarks. Many users choose to share the post on facebook and access the map that way.

Tip: Turn your phone sideways for easier use. Click the directions button top right to be routed to attraction.

Visit the worlds largest drive inn Restaurant!

Be sure to visit this record breaking institution, covering over two acres in Downtown Atlanta, Varsity is the worlds largest drive inn Restaurant and can accommodate up to 600 cars outside and over 800 people inside. The venue is especially popular when Georgia Tech plays at home.

Fun Fact: Varsity makes over two miles of Hot Dogs, 5000 fried pies and 300 gallons of Chilli daily!

Varsity worlds largest food drive in

1. Chicago to San Francisco: The Ultimate Road Trip!

San Francisco is know for its diverse cultures from the Chinatown area to its incredible food scene, iconic landmarks (golden gate bridge, Alcatraz prison island) and hipster vibe.

A road trip between Chicago and San Francisco is the ultimate road trip!

Related Read: 15 Best Waterfalls Near Chicago

How far is San Francisco to Chicago?

San Francisco is 2,132 miles from Chicago! Driving direct with no stops it would take you 31 hours!

You will cross 7 states and numerous cities of the USA! From Iowa to Nevada!

Welcome to San Francisco

Chicago to San Francisco Road Trip Itinerary:

Me & a few friends have actually taken this road trip twice! The first time we went the fastest route via Americas mid west! (Route 2).

Visiting places such as Iowa city and Denver, Colorado.

The second time we took a longer route but visited some iconic cities such a Las Vegas and LA.

We even got to see the World Largest Hot Balloon Festival in Albuquerque, New Mexico!

Wonderful Instagrammable Balloon Photos. See: 20 Golden Reasons to go Albuquerque Balloon Festival?

From LA we hopped onto the Pacific coast highway 1 which is one the 25 Most Epic Driving Roads in the U.S.A: Road Trip Ideas!

Route 1 - Las Vegas & LA Road Trip Itinerary:

  1. Chicago, IL
  2. St Louis, MO
  3. Oklahoma City, OK
  4. Albuquerque, New Mexico
  5. Las Vegas, NV
  6. Los Angeles, CA
  7. San Jose, CA
  8. San Francisco, CA

Las-Vegas-Road Trip

Route 2 - Mid West Road Trip Itinerary:

  1. Chicago, IL
  2. Iowa city, IA
  3. Kansas City, KA
  4. Denver, CO
  5. Salt Lake City, UT
  6. Reno, NV
  7. Sacramento, CA
  8. San Francisco, CA

Winter Camping at Grand Sand Dunes Colorado is a incredible experience. Source:

For more info check out: 20 Incredible Winter Camping Destinations: USA

Interactive Map (Chicago to San Francisco Road Trip):

Dive into our Interactive map below!

(The Road Trip Map outlines the two different routes mentioned above)

Route 1: Via St Louis, Albuquerque, Las Vegas and Los Angeles

Route 2: Via Iowa City, Denver, Salt Lake City and Reno.

User Guide: Use the +/- arrows to zoom in an out of the landmarks. Many users choose to share the post on facebook and access the map that way.


Tip: Turn your phone sideways for easier use. Click the directions button top right to be routed to attraction.

Related Read: 25 Best Hiking Trails Near Chicago

Should I take the California Zephyr?

The California Zephyr Amtrak train first hit the rails in was 1949. Since then it has taken rail enthusiasts on one of the most scenic train rides in the USA! Which runs between Chicago & San Francisco.

The Scenery on the California Zephyr is world renowned.  On this journey you will cross the farmlands of Nebraska, the Colorado Rockies, through the Sierra Nevada mountains before arriving at San Francisco.

California Zephyr train

The Dome Car:

The Dome Car offers seats facing out of the windows offering panoramic views of the scenery.

The Dome cars are common on scenic routes but do fill up quickly, especially on trains like the California Zephyr which passes through the untouched areas of the Colorado Rockies. So get to the carriage early to avoid disappointment.

Related Read: 15 BEST Boozy Bottomless Brunch in Chicago


Insider Tip:

Listen out for the Commentary of the most significant section of the California Zephyr route and try some classic american eggs and Bacon for breakfast in the diner carriage.

For our full guide check out our Ultimate Guide to the California Zephyr: Chicago to San Francisco

Where to Stay in San Francisco?

For a recommended list of my favourite places to stay in San Franscisco, follow the link HERE.

Vital Road Trip Tips:

Make sure you are equip with some great Photography Gear!

How to get the best car rental Deals?

Check out: Ultimate Car Rental Travel Hacks!

For RV Rentals we always use: RV Share

Bring your RV to Tiden Park.

Article updated:
January 5, 2024

You may also like...


Win a $500 Flight!

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.
*Terms apply. To participate, enter your email to sign up for the newsletter . You must be 18+ and be a resident of the US. No purchase necessary. Begins January 1st  and ends February 28th, 2024. Winner announced on March 31st. For full rules and regulations, visit our Terms & Conditions page. Data  processed according to our Privacy Policy.
Enter Sweepstakes