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By Huuk Team

Road trip from Chicago to Kansas City

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Show more (2+)

ITINERARY

9h 28m505 miles8 stops
1
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.
2
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
3
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.
4
Anderson's Bookshop
123 W Jefferson Ave, Naperville, IL 60540-5310
5
Arista Spa & Salon
2155 City Gate Ln Ste 201, Naperville, IL 60563-7703
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
6
Line Creek Trail
2699 NW 60th St, Kansas City, MO 64151
7
Howl at the Moon Kansas City
1334 Grand Blvd, Kansas City, MO 64106-2907
Howl at the Moon Kansas City is the hottest spot in the Power and Light District! Our high-energy dueling pianos and amazing events make us the coolest spot for Kansas City nightlife! From company functions to happy hour with friends to bachelorette parties in Kansas City, the party is always at Howl at the Moon come and see us.
8
Game Show Battle Rooms
10520 Metcalf Ave, Overland Park, KS 66212-1814
You're IN the Game Show! Game Show Battle Rooms is one of the nation's only immersive game show experiences for everyone to enjoy. Face-off against your friends, family, or coworkers in our custom arenas playing classic game shows! All hosted by our entertaining and engaging hosts. Perfect for your next birthday party, friend or family outing, or your next corporate team-building event!
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OVERVIEW

Get ready for an epic adventure as we embark on a journey filled with endless wonders and unforgettable moments. From the bustling streets of Chicago to the vibrant heart of Kansas City, we'll traverse vast landscapes and discover hidden gems along the way. Along this extraordinary path, we'll encounter friendly faces, marvel at breathtaking sights, and create memories that will last a lifetime.

As we set off, the towering skyscrapers of Chicago will bid us farewell, giving way to picturesque countrysides and rolling hills. We'll traverse winding roads, passing charming towns and vibrant cities, each with its own unique story to tell. The journey will be a feast for the senses, with endless vistas and the ever-changing canvas of nature's artistry.

As we approach the vibrant city of Kansas City, a symphony of culture and entertainment awaits. The bustling streets will come alive with the sounds of jazz and the aroma of delicious barbecue. We'll explore iconic landmarks, delve into captivating museums, and immerse ourselves in the city's rich history and vibrant artistic scene. The journey from Chicago to Kansas City promises to be an unforgettable adventure, filled with discoveries and moments to cherish forever.

1
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.
333 Michigan Ave, Chicago, IL 60601-3901
2
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
3
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
4
Anderson's Bookshop
Naperville, DuPage County, Illinois·
5.0
(9) review
123 W Jefferson Ave, Naperville, IL 60540-5310
5
Arista Spa & Salon
Naperville, DuPage County, Illinois·
4.0
(9) review
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
2155 City Gate Ln Ste 201, Naperville, IL 60563-7703
6
Line Creek Trail
Kansas City, Missouri·
5.0
(9) review
2699 NW 60th St, Kansas City, MO 64151
7
Howl at the Moon Kansas City
Kansas City, Missouri·
4.5
(96) review
Howl at the Moon Kansas City is the hottest spot in the Power and Light District! Our high-energy dueling pianos and amazing events make us the coolest spot for Kansas City nightlife! From company functions to happy hour with friends to bachelorette parties in Kansas City, the party is always at Howl at the Moon come and see us.
1334 Grand Blvd, Kansas City, MO 64106-2907
8
Game Show Battle Rooms
Overland Park, Kansas·
4.5
(9) review
You're IN the Game Show! Game Show Battle Rooms is one of the nation's only immersive game show experiences for everyone to enjoy. Face-off against your friends, family, or coworkers in our custom arenas playing classic game shows! All hosted by our entertaining and engaging hosts. Perfect for your next birthday party, friend or family outing, or your next corporate team-building event!
10520 Metcalf Ave, Overland Park, KS 66212-1814

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Kansas City?
The distance is 505 miles
What's the travel time between Chicago and Kansas City?
The driving time can vary depending on traffic conditions, but it is typically 9h 28m mins in normal traffic
What are some of the best cities to visit between Chicago and Kansas City?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Kansas City?
There are plenty! Here are some stops you shouldn’t miss on your way to Kansas City
What’s the weather like in Kansas City?
The weather in Kansas City is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Kansas City in January
Weather in Kansas City in February
Weather in Kansas City in March
Weather in Kansas City in April
Weather in Kansas City in May
Weather in Kansas City in June
Weather in Kansas City in July
Weather in Kansas City in August
Weather in Kansas City in September
Weather in Kansas City in October
Weather in Kansas City in November
Weather in Kansas City in December
Interested in a detailed plan for your time in Kansas City?
Plan your dream Kansas City trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Kansas City
A 2-day itinerary in Kansas City
A 3-day itinerary in Kansas City
A 4-day itinerary in Kansas City
A 5-day itinerary in Kansas City
A 6-day itinerary in Kansas City
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
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