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By Huuk Team

Road trip from Chicago to Oklahoma City

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iconNature & Parks
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ITINERARY

14h 18m788 miles11 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
Galloway Creek Greenway
2120 S Ventura Ave Pershing Middle School, Springfield, MO 65804-2718
5
Springfield Art Museum
1111 E Brookside Dr, Springfield, MO 65807-1899
6
Route 66 Car Museum
1634 W College St, Springfield, MO 65806-1614
7
BOK Center
200 S Denver Ave, Tulsa, OK 74103-5019
8
Vintage Sewing Center And Museum
5528 S Peoria Ave, Tulsa, OK 74105-6822
9
Topgolf Oklahoma City
13313 Pawnee Dr, Oklahoma City, OK 73114-1413
Topgolf is the emerging global leader in golf entertainment. Players hit golf balls containing computer microchips that track each shot’s accuracy and distance while also awarding points for hitting targets on the outfield. Topgolf offers an upscale, laid-back experience that features climate-controlled hitting bays and an impressive food and beverage menu crafted by our executive chef.
10
Brickopolis
101 S Mickey Mantle Dr, Oklahoma City, OK 73104-2480
11
Myriad Botanical Gardens
301 W. Reno, Oklahoma City, OK 73102-5030
Myriad Botanical Gardens is one of Oklahoma City’s most beloved public spaces, offering its visitors a 15 acre natural escape in the heart of downtown. A half-acre children’s garden, an off-leash dog park, splash fountains, and paths for walking and jogging provide guests young and old with a place to seek solitude with nature, or seek community and the company of others. The Gardens offers a variety of horticultural education programs for adults and children. The centerpiece attraction of the Gardens is the Inasmuch Foundation Crystal Bridge Conservatory. Its unique design has earned attention and praise in the architectural community. It is 224 feet long, 70 feet in diameter, and is covered by 3,028 sections of translucent, double-layered acrylic panels. After an 18-month, $11 million renovation, it reopened to the public on November 18, 2022.
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OVERVIEW

Welcome to a fantastic adventure from the bustling metropolis of Chicago to the serene heartland of Oklahoma City. This long journey will take you through diverse landscapes, fascinating cities, and unforgettable experiences. Along the way, you'll encounter charming small towns, witness the mighty Mississippi River, and traverse the sprawling Great Plains. Oklahoma City awaits as your final destination, offering a blend of modern attractions and rich history.

Prepare yourself for a journey of discovery as you traverse the Midwest and Southern regions of the United States. Marvel at the towering skyscrapers and vibrant culture of Chicago, and then delve into the historic battlefields and scenic byways of Tennessee. Embrace the vibrant spirit of Arkansas, home to captivating mountain vistas and charming river towns. As you approach your destination, the rolling hills and open spaces of Oklahoma will captivate your senses.

Throughout this epic journey, you'll have ample opportunities to explore hidden gems, indulge in local flavors, and create lasting memories. Whether you're an avid adventurer, a history buff, or simply seeking a change of scenery, this unforgettable road trip has something to offer everyone. So buckle up, pack your sense of wonder, and get ready for an extraordinary adventure from Chicago to Oklahoma City.

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
Galloway Creek Greenway
Springfield, Missouri·
5.0
(9) review
2120 S Ventura Ave Pershing Middle School, Springfield, MO 65804-2718
5
Springfield Art Museum
Springfield, Missouri·
4.5
(99) review
1111 E Brookside Dr, Springfield, MO 65807-1899
6
Route 66 Car Museum
Springfield, Missouri·
4.5
(95) review
1634 W College St, Springfield, MO 65806-1614
7
BOK Center
Tulsa, Oklahoma·
4.5
(907) review
200 S Denver Ave, Tulsa, OK 74103-5019
8
Vintage Sewing Center And Museum
Tulsa, Oklahoma·
5.0
(97) review
5528 S Peoria Ave, Tulsa, OK 74105-6822
9
Topgolf Oklahoma City
Oklahoma City, Oklahoma·
4.5
(92) review
Topgolf is the emerging global leader in golf entertainment. Players hit golf balls containing computer microchips that track each shot’s accuracy and distance while also awarding points for hitting targets on the outfield. Topgolf offers an upscale, laid-back experience that features climate-controlled hitting bays and an impressive food and beverage menu crafted by our executive chef.
13313 Pawnee Dr, Oklahoma City, OK 73114-1413
10
Brickopolis
Oklahoma City, Oklahoma·
4.0
(96) review
101 S Mickey Mantle Dr, Oklahoma City, OK 73104-2480
11
Myriad Botanical Gardens
Oklahoma City, Oklahoma·
4.5
(979) review
Myriad Botanical Gardens is one of Oklahoma City’s most beloved public spaces, offering its visitors a 15 acre natural escape in the heart of downtown. A half-acre children’s garden, an off-leash dog park, splash fountains, and paths for walking and jogging provide guests young and old with a place to seek solitude with nature, or seek community and the company of others. The Gardens offers a variety of horticultural education programs for adults and children. The centerpiece attraction of the Gardens is the Inasmuch Foundation Crystal Bridge Conservatory. Its unique design has earned attention and praise in the architectural community. It is 224 feet long, 70 feet in diameter, and is covered by 3,028 sections of translucent, double-layered acrylic panels. After an 18-month, $11 million renovation, it reopened to the public on November 18, 2022.
301 W. Reno, Oklahoma City, OK 73102-5030

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Oklahoma City?
The distance is 788 miles
What's the travel time between Chicago and Oklahoma City?
The driving time can vary depending on traffic conditions, but it is typically 14h 18m mins in normal traffic
What are some of the best cities to visit between Chicago and Oklahoma City?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Oklahoma City?
There are plenty! Here are some stops you shouldn’t miss on your way to Oklahoma City
What’s the weather like in Oklahoma City?
The weather in Oklahoma City is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Oklahoma City in January
Weather in Oklahoma City in February
Weather in Oklahoma City in March
Weather in Oklahoma City in April
Weather in Oklahoma City in May
Weather in Oklahoma City in June
Weather in Oklahoma City in July
Weather in Oklahoma City in August
Weather in Oklahoma City in September
Weather in Oklahoma City in October
Weather in Oklahoma City in November
Weather in Oklahoma City in December
Interested in a detailed plan for your time in Oklahoma City?
Plan your dream Oklahoma City trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Oklahoma City
A 2-day itinerary in Oklahoma City
A 3-day itinerary in Oklahoma City
A 4-day itinerary in Oklahoma City
A 5-day itinerary in Oklahoma City
A 6-day itinerary in Oklahoma 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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