Ultimate Guide to the Coolest Attractions along Route 66 from Chicago to St. Louis

From walking in Abraham Lincoln’s footsteps in Pontiac, Illinois to ascending St. Louis’s famed Gateway Arch, this guide will take you to the coolest attractions along Route 66 from Chicago to St. Louis!

If you don’t have the time to drive the entire 2,448 miles of Route 66, this abbreviated, 300-mile route is a really great option.

I love this particular Route 66 section because it highlights the best of the Midwest — a charming small town (Pontiac, Illinois), a historic capitol (Springfield, Illinois), and a bustling metropolis (St. Louis, Missouri).

I also love how perfectly-spaced each stop is. Pontiac, Springfield, and St. Louis are all about 100 miles apart. 

Without having to drive a long way to each stop, you can slow down and really enjoy the attractions I’ve highlighted below.

Route 66 road trip
I’m ready to visit all the attractions on this Route 66 list; this car though, not so much!

Here’s your Route 66 attractions roadmap:

  1. Route 66 Association of Illinois (Pontiac, Illinois)
  2. Abraham Lincoln walking tour (Pontiac, Illinois)
  3. Lincoln-Herndon Law Offices State Historic Site (Springfield, Illinois)
  4. Abraham Lincoln Presidential Library and Museum (Springfield, Illinois)
  5. Old State Capitol (Springfield, Illinois)
  6. Current Illinois State Capitol (Springfield, Illinois)
  7. Four Seasons’ Cinder House Bar and Sky Terrace (St. Louis, Missouri)
  8. The Gateway Arch (St. Louis, Missouri)
  9. St. Louis Science Center (St. Louis, Missouri)

I recommend about 3-5 days for this road trip. Though you can certainly add on several days if you plan to explore Chicago!

Note: I have articles dedicated to Chicago attractions (especially for those that like to stay active). If you have extra time to spend in Chicago at the beginning or end of your Route 66 trip, I’ve got you covered!

1. Get to Know Where You Are and Where You’re Going at the Route 66 Association of Illinois (Pontiac, Illinois)

After road-tripping about 100 miles southwest from Chicago you will arrive at your first Route 66 attraction in the charming town of Pontiac, Illinois — the Route 66 Association of Illinois.

Route 66 association

The Association’s mission is “to preserve, educate, promote and enjoy Route 66 in Illinois.”

The Association’s preservation committee is composed entirely of volunteers who are passionate about the route’s spirit and history.

Stopping here and taking the time to learn about the history and importance of Route 66 made this entire trip more meaningful.

I learned that Route 66 is nearly 100 years old! It was established in 1926 and connected my hometown, Chicago, to other important western cities.

Route 66 map roadtrip

Being a major highway, many communities sprang up along its edges. So much so that the Route 66 got the moniker “America’s Main Street.”

I also found out why Route 66 does not appear on ordinary maps. Have a guess?

It turns out that Route 66 was decommissioned as a federal highway in 1985 and was replaced by the modern interstate highway system. 

But thanks to associations like the Route 66 Association of Illinois this historic route has a second life. New signs, brochures, newsletters, community events and maps have raised awareness and renewed interest in Route 66!

Take your time exploring all the memorabilia here. It’s like looking back in time while getting a preview of what’s coming up on this route.

Route 66 attractions
Pontiac set a blogger-trap with this stunning Route 66 mural. We had to stop for a quick photo-souvenir!

Bonus: Check out this giant Route 66 mural at 110 W. Howard St. A photo here makes for a wonderful road trip memento!

2. Learn About Abraham Lincoln’s Days as a Young Lawyer on this Abraham Lincoln Walking Tour (Pontiac, Illinois)

Before you leave Pontiac to head to Springfield, spend a couple hours on this self-guided Abraham Lincoln walking tour using this “Looking for Lincoln” map.

Pontiac Illinois
Everywhere you tread here in Pontiac, you’re walking in Lincoln’s footsteps!

Doing a walking tour at my own pace is one of my favorite ways to get to know an area and its history. And Pontiac is exceedingly walker-friendly and full of interesting historic tidbits.

Did you know that Lincoln spent a lot of time in Pontiac as a young lawyer and politician? Neither did I!

Turns out, Lincoln’s presence is everywhere, from a life-sized statue in front of the Livingston County Courthouse (pictured below) to the cabin Lincoln slept in on Mill St.

Abraham Lincoln Pontiac
Missing a top-hat, but I think I nailed this Lincoln pose.

According to the map, Lincoln was one of the attorneys in the county’s first jury trial in 1840. He was 31 at the time. 

The trial was held in a log house, and the jury deliberated while sitting on logs at the bank of the Vermillion River!

By following the map I’ve linked, you will visit 12 Lincoln sites and exhibits. Stretch your legs and soak up all that history because we’re jumping back on Route 66 and heading south to…

3. Discover the Lincoln-Herndon Law Offices State Historic Site, the Only Remaining Building Where Lincoln Had a Law Office (Springfield, Illinois)

Springfield! Another 100 miles or so on Route 66 and you’ll arrive at the Illinois state capitol. 

Head to the corner of 6th and Adams to visit the Lincoln-Herndon Law Offices State Historic Site (phew that’s a mouthful).

Lincoln Herndon

Lincoln and his partner Stephen Logan moved their legal practice to the third floor of this building in 1843. Their office was right above the US District Court (which rented space on the second floor).

Plus, the building was next to the Illinois Supreme Court. Talk about a fabulous location for two budding lawyers!

Now you may be asking yourself “if Lincoln was partnered with Logan, why is the building referred to as ‘Lincoln-Herndon’?

Turns out the firm of Logan & Lincoln broke up in 1844 (yes, law firms have break-ups!), but Lincoln soon rebounded with another young lawyer named William Herndon. 

Herndon stuck around and so this historical site was preserved as the Lincoln-Herndon Law Offices State Historic Site.

Bonus: Since I can only go so long in an article before thoughts turn to food, I want to take this moment to recommend Long Nine Junction for lunch (11am-2pm, Mon.-Fri.). The garlic bread grilled cheese should have you properly carbo-loaded for our next Route 66 attraction.

4. Dive Deep into Lincoln’s Life and Legacy at the Abraham Lincoln Presidential Library and Museum (Springfield, Illinois)

If you think you’ve learned a lot about Lincoln to this point, you’re in for Lincoln-knowledge-overdose when you visit the Abraham Lincoln Presidential Library and Museum!

This 200,000 square foot complex is a mecca of knowledge about this complicated, beloved 16th president. 

Abraham Lincoln Springfield
Starting to see a theme yet? I think I took a photo with every Lincoln that I encountered on this Route 66 road trip!

Did you know that Lincoln was an accomplished wrestler as a young man? His long limbs served him well, and it is said that he was defeated only once in 300 matches!

And even though Illinois is known as the “Land of Lincoln,” he was actually born in Kentucky and lived in Indiana before moving to Illinois when he was 21.

After a visit to this museum, you’ll be annoying your friends with Lincoln trivia for decades to come!

Depending on how interested you are, I would allot 2-4 hours to explore the museum’s galleries and enjoy the theater presentations. 

If you want to see presentations like “Lincoln’s Eyes” and “Ghosts of the Library,” I would add in an extra hour or two. 

As a super-nerd I found “Ghosts of the Library” particularly interesting. This show uses Holavision holographic technology to explain the role of the Abraham Lincoln Presidential Library in “preserving not just the history of Illinois’ favorite son, but of all Illinoisans.”

Lincoln Presidential Library

Before you leave don’t forget to take an ultra-cheesy photo-op with Lincoln’s family. We fit in pretty well, no?

Bonus: The famous “Return Visit” sculpture by Seward Johnson depicting a giant Abraham Lincoln speaking about the Gettysburg Address to an unnamed “modern man” will be on display here this summer. I saw this sculpture when it came to Chicago, and it is something you definitely don’t want to miss!

5. Admire the Greek Revival Architecture of the Old State Capitol (Springfield, Illinois)

It’s impossible to explore Springfield without being awed by the Old State Capitol building. If you’re a fan of architecture, history or both, you won’t regret adding this site to your Route 66 bucketlist!

Plus it’s a 3 minute walk from the Abraham Lincoln Presidential Library and Museum so pairing these two attractions is a no-brainer. 

Even though the Old State Capitol is a bit brown-on-brown for my taste, it is still a beauty. The building was designed in the Greek Revival style by local architect John Francis Rague, and it was completed in 1840.

Illinois Old State Capitol

Look closely and you can see the locally-quarried yellow Sugar Creek limestone used in its construction.

Lincoln pleaded cases before the Illinois State Supreme Court in this building and served his last term as a state lawmaker here in 1840-41. Lincoln also announced his candidacy for the US Senate here and made his famous “House Divided” speech in June of 1858.

“A house divided against itself cannot stand. I believe this government cannot endure, permanently, half slave and half free.”

-Abraham Lincoln, June 16, 1858

By the 1870s, this building was considered too small to serve as the State Capitol so the capitol moved 4 blocks southwest, and this building turned into a county courthouse.

Then in the 1960’s, there was a movement to restore the Old State Capitol building to its original form. Life came full circle for this historic structure as the House Chamber was rebuilt and the interior was restored.

Nowadays, the Old State Capitol is used for ceremonial functions like the time then-Senator Barack Obama announced his candidacy for President of the United States!

If you want to see the restoration first hand, I recommend going on the 30-minute tour and then exploring at your own pace. 

6. Complete Your Illinois Explorations at the Beautiful Illinois State Capitol (Springfield, Illinois)

No need to hop back in your car just yet. Walk about half a mile southwest from the Old State Capitol and you’ll get to the next stop on this Route 66 attractions tour — the new state capitol.

Illinois State Capitol
Looks like the Illinois State Capitol came straight out of Europe, doesn’t it?

The Illinois State Capitol is a beautiful blend of French Renaissance and Italianate styles, designed by the architecture firm of Cochrane and Garnsey. 

Look up and you’ll see the stunning 405-foot dome.

Fun fact — the central dome and tower roofs are covered in zinc which gives them a silvery, weather-resistant facade!

Even though I only had time to enjoy the grounds here, I recommend going inside for the full experience. And if you time your visit for when the legislature is in session, you may be able to watch Illinois politics live from the balcony-level seating!

7. Enjoy Brunch with a Side of Views at the Cinder House Bar and Sky Terrace at the Four Seasons (St. Louis, Missouri)

Next, we’re leaving Illinois in the rearview and heading about 100 miles south on Route 66 to St. Louis, Missouri!

I have a little secret to share with you about how I keep my energy levels up for a full day of explorations — I start the day with a hearty, delicious brunch!

And there is no better brunch in St. Louis than at the Four Seasons’ Cinder House Bar and Sky Terrace

I arrived fairly early and was able to snag a table on the pool deck surrounded by views in every direction. I could see the Martin Luther King Bridge, the Mississippi River, and the famed Gateway Arch. WOW!

Being from Chicago, I’m spoiled when it comes to jaw-dropping city views, but the view from the Sky Terrace really impressed me!

When the views are this good, I start to worry about the quality of the food, but my fears were unfounded here. 

James Beard Award-Winning Chef Gerard Craft is churning out some truly delectable plates, blending the tradition of wood-fired cuisine with bold international flavors. 

“With an eye on the entire world, but a heavy hand toward South America, a meal at Cinder House is always flickering with surprises.”

-Cinder House, Four Seasons in St. Louis

After scanning the menu several times, I chose the salmon sandwich. Everything about this sandwich was perfection: from the plump cut to the seasoning to the doneness.

Four Seasons brunch
I took the top off so you could see all that deliciousness!

I am literally salivating in memory of it as I am uploading the photograph above!

Bonus: If you come here on a Sunday (or you plan your trip so that you are here on a Sunday — and I wouldn’t judge you if you do), you can indulge in the brunch buffet. The lavish spread includes a raw seafood bar, sliders station, fresh juices and warn, made-to-order donuts!!

8. Get a Bird’s-Eye-View of St. Louis From Atop The Gateway Arch (St. Louis, Missouri)

Now that you’re properly fueled, you’re ready to see St. Louis from the tippity-top of America’s tallest man-made monument — the Gateway Arch.

The Gateway Arch was designed by artist and architect Eero Saarinen who won a 1948 design competition with his sleek, stainless steel arch. 

Gateway Arch St Louis

Since its completion in 1965, the Gateway Arch has welcomed millions of visitors!

Getting to the top is an experience in and of itself. In the tram waiting area, there are interactive exhibits featuring 60s era animations and Gateway Arch trivia. 

I should note that although riding the tram to the top of the Gateway Arch is one of my favorite Route 66 attractions, if you are claustrophobic, you may want to enjoy it from the ground.

Check out this link to get a preview of the tram experience, and see if it’s right for you!

If you do brave the tram experience, you’ll be transported 630 feet above the city for some truly breath-taking views over St. Louis!

Route 66 Missouri
I would ride the tiny tram several times over for this iconic St. Louis view!

Bonus: If you have time, the Museum at Gateway Arch is also a worthwhile visit. There you can learn 201 years of history covering the US’s westward expansion and St. Louis’s role in that era. I especially appreciated the shared perspectives of those affected by colonialism (namely, indigenous and Creole people who lived here long before the Louisiana Purchase).

9. Geek-Out at the St. Louis Science Center (St. Louis, Missouri)

While I was on this Route 66 adventure a storm was hot on my heels, and it finally caught up with me on my second day in St. Louis.

After some quick googling I found the perfect rainy-weather activity — the St. Louis Science Center.

Did you know that the Science Center is one of the nation’s only free, nonprofit museums? That’s right, general admission is always free here!

Route 66 stop

Even though admission is free, you’ll be impressed at the quality and depth of the content here. If you’re into fossils, dinosaurs, planets, galaxies and space-travel, this is the place for you.

As a kid, I had a subscription to a dinosaurs magazine (it even had a dino-centerfold!). I also collected dinosaur figurines and watched all the dino-programing that I could get my eyeballs on.

I was in heaven at the Science Center.

At one point, I reached geek-nirvana as I spotted the periodic table with my favorite element — Einsteinium!

st louis science center

Bonus: Don’t miss out on the Planetarium shows like “Gateway to the Solar System.” You’ll learn about new discoveries in our solar system and beyond, as well as past, present, and future planetary phenomena!

Phew! 300 miles, 3 cities (4 if you added on Chicago!) and 9 Route 66 attractions.

I hope this bucketlist of Route 66 attractions from Chicago to St. Louis is getting you excited to plan your own Route 66 road trip!

And if you’re already in St. Louis, I recommend flipping this list and doing the route in reverse, heading north to Chicago. Chicago is a great place to start or end this adventure!

Which of the route 66 attractions above has you most excited?

Have you traveled this route before? If so, what would you add to the list above? Let me know in the comments below!

Note: Due to covid, I highly recommend going on these Route 66 attractions’ websites to check their hours and visit guidelines. I would hate for you to miss out on seeing any of these places because hours have changed or you didn’t get an advanced entry ticket!

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9 thoughts on “Ultimate Guide to the Coolest Attractions along Route 66 from Chicago to St. Louis”

    • Thank you for the kind words Jessica and for taking the time to read this post! I hope you get to do the Midwestern section of Route 66 one day; I think you’d really enjoy it! 🙂

  1. A wonderful adventure on this road trip! All the Lincoln attractions would be so interesting; didn’t know about all that info when he was a youth. I would just love the Science Center, and we need to visit Gateway Arch, since its a National Park. Great post Alana!

    • Thank you Shannon, I tried to pack it in with the best of the best! There really is a ton to learn and enjoy on this route. When you do go, let me know what you think! 🙂

    • That’s amazing Lannie; you were very well-situated for some great explorations! And thank you for taking the time to read this article (I hope it inspires future adventures!)

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