By Huuk Team
Share Your Trip
Excited about your upcoming trip? Share the adventure with your friends!
Road trip from Chicago to San Antonio
All Category
Nightlife
Fun & Games
Shopping
Concerts & Shows
Sights & Landmarks
Museums
Outdoor ActivitiesShow more (1+)
All Category
NightlifeFun & GamesShoppingConcerts & ShowsSights & LandmarksMuseumsOutdoor ActivitiesReset
Show less
ITINERARY
22h 4m1,193 miles23 stops
1
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
2
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
3
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.
4
Peoria PlayHouse Children's Museum
The Peoria PlayHouse Children's Museum provides children with the tools and inspiration they need to be explorers and creators of the world. We do this in part through understanding, supporting, and promoting play in the fullest sense of the word, one that includes imagination and creativity.
5
Galloway Creek Greenway
6
Springfield Art Museum
7
Route 66 Car Museum
8
Port City Raceway
9
Tulsa Raceway Park
10
Tam Bao Buddist Temple
11
BOK Center
12
Vintage Sewing Center And Museum
13
PanIQ Room Dallas
14
Central Market
15
Waco Hippodrome Theatre
The Historic Waco Hippodrome Theatre is back! Come enjoy delicious food and refreshing drinks as you sit back, relax, and watch your favorite films, live music, and performing arts. First opening on February 7, 1914, The Waco Hippodrome Theatre is a landmark in entertainment for the Waco community. After some tender-loving renovations, the Waco Hippodrome Theatre is open and busier than ever! Our dining room and bar/lounge area are open Mon-Fri for lunch and dinner, and we open at 10:00 am on Saturdays and Sundays to serve the best brunch in Downtown Waco.
16
The Texas Collection
Established in 1923, The Texas Collection is a special library, archival research center, and the University Archive that collects, preserves, and provides access to materials documenting the history, heritage and culture of Texas for the Baylor community and the public.
17
Little Shop on Bosque
The Little Shop on Bosque is the original home of Magnolia Market and offers last chance and slightly damaged items at a discount. The shop is stocked with everything from florals to vases, apparel to gifts, and so much more. *Please note that all sales at our Little Shop on Bosque are final. You cannot receive a replacement or refund on any sales.
18
Mindspark Adventures and Escape Games
Mind Spark is a fully interactive and immersive experience unlike anything else you can do in Austin, Texas. Up to 12 participants will be locked in a room, and they must use their minds and teamwork to figure out their escape. Clues and riddles hidden throughout the room provide the tools necessary to win the game and get out of the room. As the clock ticks down and the pressure mounts, can you stay calm, can you escape?
19
Saxon Pub
20
Purrfecto Cat Lounge
We partner with local rescues to temporarily house cats. Book a CatXperience and be surrounded by love-able furrballs. You might find your next furry friend!
21
Santikos Palladium IMAX
22
Extreme Escape
Extreme Escape San Antonio is the FIRST to offer four different themed escape experience. Mutiny and Trapped Below have broad appeal, including puzzle loving families and children ages 9 and above, while Undead and Master of Illusion are suitable for teenagers and adults looking for a thrill. We’ve incorporated multi-dimensional elements like life-sized props, special effects and even smells to make your “escape” amazing!
23
Paramour Roof Top Bar
Customize this Trip
OVERVIEW
Prepare for an epic adventure as we embark on an unforgettable road trip from the bustling metropolis of Chicago to the vibrant city of San Antonio. Along the way, we'll traverse vast landscapes, encounter diverse cultures, and create memories that will last a lifetime.
From the shores of Lake Michigan, we'll wind our way through the heartland of America, passing charming towns and rolling hills. The open road will stretch before us, beckoning us to explore the unknown and embrace the freedom of the highway. As we approach the Lone Star State, the landscape will transform into a vast and arid desert, dotted with towering cacti and rugged mountain ranges.
As we finally pull into San Antonio, a vibrant tapestry of history, culture, and modern amenities awaits. We'll immerse ourselves in the city's rich heritage, from the iconic Alamo to the lively River Walk. The aroma of Tex-Mex cuisine will fill the air, inviting us to savor the flavors of the Southwest.
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.
2
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
3
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.
4
Start:Peoria PlayHouse Children's Museum
Peoria, Illinois·
4.5
(84) review
The Peoria PlayHouse Children's Museum provides children with the tools and inspiration they need to be explorers and creators of the world. We do this in part through understanding, supporting, and promoting play in the fullest sense of the word, one that includes imagination and creativity.
5
Start:Galloway Creek Greenway
Springfield, Missouri·
5.0
(9) review
2120 S Ventura Ave Pershing Middle School, Springfield, MO 65804-2718
6
Start:Springfield Art Museum
Springfield, Missouri·
4.5
(99) review
1111 E Brookside Dr, Springfield, MO 65807-1899
7
Start:Route 66 Car Museum
Springfield, Missouri·
4.5
(95) review
1634 W College St, Springfield, MO 65806-1614
8
Start:Port City Raceway
Tulsa, Oklahoma·
4.5
(3) review
1706 N 161st East Ave, Tulsa, OK 74116-4825
9
Start:Tulsa Raceway Park
Tulsa, Oklahoma·
4.5
(21) review
3101 N Garnett Rd, Tulsa, OK 74116-1219
10
Start:Tam Bao Buddist Temple
Tulsa, Oklahoma·
4.5
(6) review
16933 E 21st St, Tulsa, OK 74134-2102
11
Start:BOK Center
Tulsa, Oklahoma·
4.5
(907) review
200 S Denver Ave, Tulsa, OK 74103-5019
12
Start:Vintage Sewing Center And Museum
Tulsa, Oklahoma·
5.0
(97) review
5528 S Peoria Ave, Tulsa, OK 74105-6822
13
Start:PanIQ Room Dallas
Dallas, Texas·
4.5
(99) review
5302 Belt Line Rd, Dallas, TX 75254-7606
14
Start:Central Market
Dallas, Texas·
4.5
(99) review
5750 E Lovers Ln, Dallas, TX 75206-2921
15
Start:Waco Hippodrome Theatre
Waco, Texas·
4.0
(92) review
The Historic Waco Hippodrome Theatre is back! Come enjoy delicious food and refreshing drinks as you sit back, relax, and watch your favorite films, live music, and performing arts. First opening on February 7, 1914, The Waco Hippodrome Theatre is a landmark in entertainment for the Waco community. After some tender-loving renovations, the Waco Hippodrome Theatre is open and busier than ever! Our dining room and bar/lounge area are open Mon-Fri for lunch and dinner, and we open at 10:00 am on Saturdays and Sundays to serve the best brunch in Downtown Waco.
16
Start:The Texas Collection
Waco, Texas·
5.0
(9) review
Established in 1923, The Texas Collection is a special library, archival research center, and the University Archive that collects, preserves, and provides access to materials documenting the history, heritage and culture of Texas for the Baylor community and the public.
17
Start:Little Shop on Bosque
Waco, Texas·
3.5
(93) review
The Little Shop on Bosque is the original home of Magnolia Market and offers last chance and slightly damaged items at a discount. The shop is stocked with everything from florals to vases, apparel to gifts, and so much more. *Please note that all sales at our Little Shop on Bosque are final. You cannot receive a replacement or refund on any sales.
18
Start:Mindspark Adventures and Escape Games
Austin, Texas·
5.0
(99) review
Mind Spark is a fully interactive and immersive experience unlike anything else you can do in Austin, Texas. Up to 12 participants will be locked in a room, and they must use their minds and teamwork to figure out their escape. Clues and riddles hidden throughout the room provide the tools necessary to win the game and get out of the room. As the clock ticks down and the pressure mounts, can you stay calm, can you escape?
19
Start:Saxon Pub
Austin, Texas·
4.5
(97) review
1320 S Lamar Blvd, Austin, TX 78704-2387
20
Start:Purrfecto Cat Lounge
Austin, Texas·
5.0
(97) review
We partner with local rescues to temporarily house cats. Book a CatXperience and be surrounded by love-able furrballs. You might find your next furry friend!
21
Start:Santikos Palladium IMAX
San Antonio, Texas·
4.5
(96) review
17703 W Interstate 10, San Antonio, TX 78257-9529
22
Start:Extreme Escape
San Antonio, Texas·
5.0
(966) review
Extreme Escape San Antonio is the FIRST to offer four different themed escape experience. Mutiny and Trapped Below have broad appeal, including puzzle loving families and children ages 9 and above, while Undead and Master of Illusion are suitable for teenagers and adults looking for a thrill. We’ve incorporated multi-dimensional elements like life-sized props, special effects and even smells to make your “escape” amazing!
23
Start:Paramour Roof Top Bar
San Antonio, Texas·
3.5
(93) review
102 9th St 4th Floor, San Antonio, TX 78215-1524
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
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Chicago to Philadelphia
758 miles
14h 3m
20 stops
Museums
Food & Drink
ToursSights & LandmarksShoppingChicago to San Jose
2,167 miles
37h 30m
26 stops
Sights & Landmarks
Nature & ParksOutdoor ActivitiesTours
Water & Amusement ParksChicago to Columbus
355 miles
6h 49m
19 stops
Sights & LandmarksToursWater & Amusement ParksFun & Games
Spas & WellnessChicago to San Francisco
2,135 miles
36h 54m
27 stops
Sights & LandmarksNature & ParksFood & DrinkToursWater & Amusement ParksChicago to Seattle
2,055 miles
36h 4m
16 stops
Sights & Landmarks
OtherNature & ParksMuseumsFun & GamesChicago to Denver
1,002 miles
17h 42m
13 stops
Food & DrinkSpas & WellnessOtherShoppingToursEXPLORE OTHER
Check Out Different Road Trip Options
Scranton to Bremerton
2,798 miles
49h 56m
24 stops
Sights & LandmarksFood & DrinkFun & GamesMuseumsOtherSanta Ana to Santa Clarita
67 miles
1h 23m
16 stops
Outdoor ActivitiesMuseumsShoppingSights & Landmarks
Traveler ResourcesLexington to Rancho Cucamonga
2,121 miles
37h 12m
29 stops
Traveler ResourcesNature & ParksMuseumsSights & LandmarksToursCorpus Christi to Gainesville
1,068 miles
19h 56m
34 stops
Fun & GamesShoppingSights & LandmarksNature & ParksOutdoor ActivitiesSanta Cruz to Killeen
1,702 miles
30h 38m
32 stops
Food & DrinkWater & Amusement Parks
Classes & WorkshopsFun & GamesNature & ParksColorado Springs to Lexington
1,168 miles
21h 5m
18 stops
Sights & LandmarksTraveler ResourcesShoppingFood & DrinkToursFAQ
Frequently Asked Questions
What's the driving distance between Chicago and San Antonio?
The distance is 1,193 miles
What's the travel time between Chicago and San Antonio?
The driving time can vary depending on traffic conditions, but it is typically 22h 4m mins in normal traffic
What are some of the best cities to visit between Chicago and San Antonio?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to San Antonio?
There are plenty! Here are some stops you shouldn’t miss on your way to San Antonio
What’s the weather like in San Antonio?
The weather in San Antonio is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in San Antonio in January
Weather in San Antonio in February
Weather in San Antonio in March
Weather in San Antonio in April
Weather in San Antonio in May
Weather in San Antonio in June
Weather in San Antonio in July
Weather in San Antonio in August
Weather in San Antonio in September
Weather in San Antonio in October
Weather in San Antonio in November
Weather in San Antonio in December
Interested in a detailed plan for your time in San Antonio?
Plan your dream San Antonio trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in San Antonio
A 2-day itinerary in San Antonio
A 3-day itinerary in San Antonio
A 4-day itinerary in San Antonio
A 5-day itinerary in San Antonio
A 6-day itinerary in San Antonio
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
