St Louis to Chicago – How to Enjoy an Epic Midwest Road Trip

Published Date:

Last Updated:

Share post:

Road trips are a great way to explore new places and stumble across hidden gems. While the US is home to a plethora of amazing iconic road trips, some of the lesser known road trip experiences are equally spectacular. The Midwest may not be the first area of the US you think about visiting (unless you are located in this part of the country) but for those of you intrigued by the thought of exploring states such as Illinois, Indiana and Missouri, this is definitely an area you should consider. One of our favorite road trips in this part of the US is between St Louis and Chicago – two iconic cities that you can certainly enjoy on their own, but when you combine both into the same trip, it creates an awesome experience that is definitely worth experiencing in either a long weekend getaway or longer.

st louis gateway arch national park

Whether you have visited St Louis or Chicago previously, this is a road trip that is well worth experiencing if you are intrigued by the prospect of exploring the heart and soul of the Midwest. Both cities offer spectacular attractions but there are several things to do along this road trip that will likely justify making a few stops along this route. Let’s start out by taking a look at which routes are available and you can choose which one you prefer based on the time you have, along with experiences you want to encounter along the chosen itinerary.

navy pier chicago

Road Trip from St Louis to Chicago

From the Gateway City to the Windy City and everything in between, this is a road trip that will long live in your memory as you experience the myriad of things to do in this part of the Midwest. Dependent on how much time you choose to allocate to this road trip will likely determine the optimal route, but we would encourage you to follow what is considered the most direct route along I-55 as this is not only the quickest, but it also offers a collection of awesome places that you may fall in love with.

forest park st louis

However, we are going to add a slight detour at the beginning of the trip as you venture outside of the Gateway City because the hidden gem of St. Charles, Missouri is well worth experiencing before you head towards Illinois.

If history, architecture and Midwest culture is what you are wanting to experience during this road trip, you have come to the right place as you follow our recommended itinerary between these two amazing cities. We are going to share some of the iconic destinations along this journey, while also offering a few things to do in the host and destination city.

  • St Louis, Missouri
  • St. Charles, Missouri
  • Springfield, Illinois
  • Bloomington, Illinois
  • Starved Rock State Park, Illinois
  • Chicago, Illinois

Total Distance – 365 miles
Duration – 6 hours

st louis to chicago map

Click here to open Google Maps for step by step guided directions

Things to Do in St Louis

You could be forgiven for wanting to stay in St. Louis for several days before venturing on the road trip to Chicago because there are plenty of things to experience in this part of Missouri. Located along the banks of the Mississippi River, St. Louis is home to a myriad of iconic attractions including Anheuser Busch Brewery, Gateway Arch National Park and of course, Busch Stadium, home of the MLB team – St. Louis Cardinals.

busch stadium st louis

One of the most attractive characteristics of St. Louis for visitors is the plethora of free attractions that are available. A guided tour of the brewery that brews the iconic Budweiser brand or perhaps a visit to the spectacular St. Louis Zoo in the heart of Forest Park are just two examples of free attractions that would likely involve an admission fee in any other city.

gateway arch st louis

St. Louis is also home to a collection of diverse neighborhoods, ranging from eclectic foodie areas such as The Hill (definitely a hotspot for authentic Italian cuisine) and Delmar Loop, to regions of the city that are home to historic architecture like Lafayette Square. If you are truly looking for an off the beaten path experience in St. Louis, head to one of the lesser known neighborhoods for a true local’s experience of the city.

downtown st louis waterfall

Things to Do in St. Charles

While the most direct route to Chicago from St. Louis may see you head across the Mississippi River through the Eastern side of the city, we strongly encourage you to take a slight detour to the north-west and venture to the historic nearby town of St. Charles. Widely recognized as the starting point of the iconic Lewis and Clark expedition in 1804, this quirky, idyllic town is certainly a spot that epitomizes American history and proudly continues to maintain the cobblestone streets that are typical of a Victorian-esque location.

st charles missouri

Spend some time along Main Street in the historic quarter of St. Charles, admiring the historic architecture that have been transformed into local, boutique establishments or quaint cafes offering stereotypical local cuisine. With ample parking along the street, you can walk along perusing inside the local stores before meandering your way down to the riverfront to perhaps imagine what Lewis and Clark faced during the 19th century expedition on the Mississippi River.

historic district st charles

The historic train station and depot last saw a passenger train in the mid-20th century but today, it offers an iconic reflection on what was once a thriving industry and perhaps one that many Americans would like to see restored especially when compared with the European train system that offers such a convenient way to connect between cities.

st charles train depot

Things to Do in Springfield

Keeping the tradition of historic locations on the route between St. Louis and Chicago, head to the state capital of Illinois to visit the historic city of Springfield. While the State Capitol building is a must-see for any architecture aficionados out there, this structure is frequently left in the shadow of Springfield’s most iconic buildings, primarily due to their association.

illinois state capitol building

Springfield is the site of Abraham Lincoln’s former home where he resided between 1844 and 1861 before starting his tenure as the 16th President of the United States.

lincoln home springfield

While a trip to Springfield should certainly include a guided tour of Lincoln’s former home, visitors should also take time to explore the historic neighborhood that Lincoln called home for 17 years. Another iconic location is Lincoln’s Tomb where you can pay your respects and tribute to one of America’s most infamous leaders.

springfield illinois

Things to Do in Bloomington

Whether you are inspired by the thought of visiting a Victorian mansion or perhaps want to explore a history museum, a short drive from Springfield will lead you to another of Illinois’ iconic cities – Bloomington. The David Davis mansion, also known as Clover Lawn, dates back to 1870 and is the former home of Supreme Court justice and Senator from Illinois – it has been converted into a state museum since 1960. The Blair Dunning house is another site worth visiting for anyone that loves historic architecture.

blair dunning house bloomington

The McLean County Museum of History is definitely a worthwhile visit for any aspiring historians while those looking to explore the great outdoors may prefer to visit Miller Park, a public area of green space in the southwest region of the city and also home to Miller Park Zoo. The Children’s Discovery Museum in Bloomington is a great visit for all the family to enjoy while Constitution Trail is a hikers/bikers dream as it covers 24 miles of former railway line.

bloomington constitution trail

Things to Do at Starved Rock State Park

Before arriving in the city of Chicago, take some time to visit Starved Rock State Park located along the Illinois River. This area is renowned for the the sandstone canyons where visitors can walk through and enjoy the spectacular scenery. For waterfall lovers, there are several of these canyons that are home to breathtaking falls, so be prepared to spend some time exploring this part of the state.

starved rock state park

A myriad of hiking trails are available, ranging from short hikes to those that are a little more challenging and lengthy. The hike to Starved Rock itself is a short 15-minute trip from the Visitor’s Center, but there are plenty of other options available dependent on how much time you allocate to this state park.

Things to Do in Chicago

While you could easily spend several days exploring the plethora of attractions in the city of Chicago, we would encourage you to immediately head downtown to experience some of the infamous structures that we all immediately associate with the Windy City! Take a trip to the summit of Willis Tower, which upon its initial construction in 1973 became the world’s tallest structure, surpassing the World Trade Center in New York City.

willis tower chicago skyline

The Skydeck Chicago at Willis Tower is an amazing experience as you step foot on the glass deck that towers above the city – it’s certainly not for the faint-hearted, particularly those with a fear of heights but its a great way to overcome those fears! Other iconic attractions in the downtown neighborhood include Cloud Gate (known as “The Bean”) at Millennium Park, The Magnificent Mile (Chicago’s premier commercial district) and Navy Pier.

downtown chicago

Chicago’s collection of vibrant neighborhoods offer some of the best eateries in the US, and obviously a trip wouldn’t be the same without sampling a variety of deep dish pizza options – some of the best locations include Lou Malnati’s, Giordano’s and Bartoli’s.


From history to delicious stereotypical deep-dish pizza, a road trip from St Louis to Chicago offers travelers the opportunity to explore a myriad of amazing attractions and sample decadent local restaurants. Whether you are intrigued by the thought of exploring the great outdoors in Forest Park or Laumeier Sculpture Park, or perhaps prefer the idea of heading downtown St. Louis to admire the quintessential Gateway Arch, there are plenty of reasons to justify staying the west side of the Mississippi River.

springfield illinois

However, with historic urban destinations such as Springfield, Bloomington and of course, Chicago, you will certainly be spoiled for choice with things to do when you head into Illinois. A Midwest road trip between these two iconic cities is something that we strongly encourage anyone wanting to explore the best of both states to experience. What are your favorite things to do in St. Louis and Chicago (or between them)?

Share on Social...

Chris Boothman
Chris Boothman is the co-founder of A Brit and A Southerner. Born near Manchester, England, Chris moved to USA in 2006 where he soon after met his wife and travel partner in crime, Heather. They have since embarked on an amazing journey of travel as they challenge others to follow in their paths of working full-time but also being able to travel frequently! If you have any questions or comments, please feel free to contact Chris at [email protected]



Please enter your comment!
Please enter your name here