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By Huuk Team

Road trip from Chicago to Evansville

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ITINERARY

6h 22m287 miles12 stops
1
Museum Of Illusions Chicago
25 E Washington St, Chicago, IL 60602-1708
2
The Chopping Block
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
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.
3
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.
4
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
5
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.
6
Derby City Gaming Downtown
140 South 4th St., Louisville, KY 40202
Play it up downtown at Louisville’s hottest play—Derby City Gaming Downtown! Like slots? You’ll love Derby City Gaming Downtown! Spin and win on close to 500 thrilling games like Buffalo, Wheel of Fortune and more on the main non-smoking gaming floor and an open-air smoking and gaming patio. Bring your night to life at three lively bars and lounges. First Turn Sports Bar is your homefield for fun, featuring delicious food and convenient sports betting kiosks for watching and wagering on all the games. Sip the finest bourbons and sample a variety of cigars at The Trophy Bar—all while surrounded by actual trophies from legendary horse races. Stop and smell the Rosé at the Fascinator Wine Bar, featuring delectable charcuterie plates and other savory selections. No visit is complete without taking a spin through the Kentucky Derby Gift Shop where you’ll find a variety of 150TH Kentucky Derby merchandise and more unique souvenirs. Must be 21 or older. Gambling problem? Call 1-800-GAMBLER.
7
Wesselman Woods Nature Center
551 N Boeke Rd, Evansville, IN 47711-5923
8
Sportsman's Grille & Billiards
2315 W Franklin St, Evansville, IN 47712-5118
9
Willard Library
21 N 1st Ave, Evansville, IN 47710-1294
10
Evansville Brewhouse
56 Adams Ave, Evansville, IN 47713-1310
11
Mo's House
1114 Parrett St, Evansville, IN 47713-1344
12
Burdette Park
5301 Nurrenbern Rd, Evansville, IN 47712-9368
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OVERVIEW

Your adventure begins in the bustling metropolis of Chicago, where towering skyscrapers reach for the sky and the energy of the city pulses through its streets. As you board your train and settle into your comfortable seat, anticipation fills the air as you prepare for an unforgettable journey.

The train glides smoothly out of the station, carrying you through the vibrant heart of the Midwest. As you gaze out the window, the urban landscape gives way to rolling hills and verdant fields. The rhythm of the tracks provides a soothing backdrop as you lose yourself in the passing scenery.

Your destination awaits in the charming city of Evansville, where the Ohio River meanders gracefully through the heart of downtown. As the train pulls into the station, you disembark and step into a world of Southern hospitality and Midwestern charm. The adventure that lies ahead promises to create memories that will last a lifetime.

1
Start:Museum Of Illusions Chicago
Chicago, Illinois·
4.5
(97) review
25 E Washington St, Chicago, IL 60602-1708
2
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.
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
3
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
4
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
5
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
6
Derby City Gaming Downtown
Louisville, Kentucky·
(0) review
Play it up downtown at Louisville’s hottest play—Derby City Gaming Downtown! Like slots? You’ll love Derby City Gaming Downtown! Spin and win on close to 500 thrilling games like Buffalo, Wheel of Fortune and more on the main non-smoking gaming floor and an open-air smoking and gaming patio. Bring your night to life at three lively bars and lounges. First Turn Sports Bar is your homefield for fun, featuring delicious food and convenient sports betting kiosks for watching and wagering on all the games. Sip the finest bourbons and sample a variety of cigars at The Trophy Bar—all while surrounded by actual trophies from legendary horse races. Stop and smell the Rosé at the Fascinator Wine Bar, featuring delectable charcuterie plates and other savory selections. No visit is complete without taking a spin through the Kentucky Derby Gift Shop where you’ll find a variety of 150TH Kentucky Derby merchandise and more unique souvenirs. Must be 21 or older. Gambling problem? Call 1-800-GAMBLER.
140 South 4th St., Louisville, KY 40202
7
Wesselman Woods Nature Center
Evansville, Indiana·
4.5
(75) review
551 N Boeke Rd, Evansville, IN 47711-5923
8
Sportsman's Grille & Billiards
Evansville, Indiana·
3.5
(7) review
2315 W Franklin St, Evansville, IN 47712-5118
9
Willard Library
Evansville, Indiana·
4.5
(97) review
21 N 1st Ave, Evansville, IN 47710-1294
10
Evansville Brewhouse
Evansville, Indiana·
4.5
(9) review
56 Adams Ave, Evansville, IN 47713-1310
11
Mo's House
Evansville, Indiana·
4.5
(9) review
1114 Parrett St, Evansville, IN 47713-1344
12
Burdette Park
Evansville, Indiana·
4.0
(95) review
5301 Nurrenbern Rd, Evansville, IN 47712-9368

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Evansville?
The distance is 287 miles
What's the travel time between Chicago and Evansville?
The driving time can vary depending on traffic conditions, but it is typically 6h 22m mins in normal traffic
What are some of the best cities to visit between Chicago and Evansville?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Evansville?
There are plenty! Here are some stops you shouldn’t miss on your way to Evansville
What’s the weather like in Evansville?
The weather in Evansville is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Evansville in January
Weather in Evansville in February
Weather in Evansville in March
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Weather in Evansville in December
Interested in a detailed plan for your time in Evansville?
Plan your dream Evansville trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Evansville
A 2-day itinerary in Evansville
A 3-day itinerary in Evansville
A 4-day itinerary in Evansville
A 5-day itinerary in Evansville
A 6-day itinerary in Evansville
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you