Day Trips Family Fun Illinois Travel Guides Weekend Getaways September 25, 2024 7 min read

Hidden Gems of Chicago: Underrated Spots Most Tourists Miss

The image shows a wide-angle aerial view of downtown Chicago with its iconic skyline, including prominent skyscrapers like the Willis Tower and John Hancock Center. In the foreground is a lush, green park area featuring trees, ponds, and walking paths, which appears to be part of Lincoln Park. To the left, Lake Michigan is visible under a partly cloudy sky. The blend of urban architecture and natural greenery creates a striking contrast in this scenic shot of the city.
Skyline view of Chicago

Exploring Chicago and Beyond

When most people think of Chicago, the usual suspects come to mind. Navy Pier, Millennium Park, the Magnificent Mile.

And sure, those are great. But Chicago and the surrounding area have a whole other side that most visitors never see.

We’ve been exploring the Windy City and its suburbs for years and have put together this list of hidden gems, underrated day trips, and lesser known spots that are absolutely worth your time.

The image shows a view of the Field Museum in Chicago, situated in Museum Campus, with a backdrop of the city's skyline. The neoclassical museum building is surrounded by green lawns, trees, and walking paths, with a large spherical sculpture visible in the foreground. Towering skyscrapers, including the Willis Tower, stand tall under a bright blue sky dotted with white clouds, adding an urban contrast to the peaceful park setting.
The Field Museum of Chicago

Whether you’re a local or planning a visit, here are some things to do in Chicago and its nearby areas that often fly under the radar:

Ricobene’s Famous Breaded Steak Sandwich

A nighttime street scene featuring a lit neon sign that reads, "EAT at Ricobene's Since 1946," with green and red lettering and a checkered border. The surroundings include parked cars, street lights, and a sign for "St. Jerome Croatian Church" near a stop sign in the background. The dim lighting adds a cozy, urban vibe.

Before heading out of town, make sure to stop by Ricobene’s for their legendary breaded steak sandwich. A true Chicago classic, this hearty sandwich is packed with perfectly breaded steak, marinara sauce, and melted cheese, all wrapped up in a fresh roll.

Known as one of the best sandwiches in Chicago, Ricobene’s has been serving up this local favorite for decades. Whether you’re grabbing a bite before your next adventure or capping off a day of exploring, a visit to Ricobene’s is a must!

Volo Auto Museum — Volo, Illinois

The image shows a sign for the "World Famous Volo Museum" in Volo, Illinois. The sign features a turquoise classic car, likely from the 1950s, and an illustration of Betty Boop in a retro outfit standing beside it, wearing roller skates. The top of the sign is bordered with a marquee-style design, evoking a vintage, Hollywood-inspired theme. The setting around the sign is outdoors, with greenery and a parking area in the background.

About an hour north of Chicago in Volo, Illinois, the Volo Auto Museum is one of the most underrated family destinations in the entire Midwest.

The museum houses a massive collection of antique cars, vintage motorcycles, and actual movie and TV cars you will recognize immediately. It’s endlessly fun for car enthusiasts and casual visitors alike and the whole family will find something to love.

You can check out one of a few videos we’ve made on the Volo Museum on our YouTube channel here.

Six Flags Great America — Gurnee, Illinois

Thrill-seekers will love visiting Six Flags Great America, a massive theme park situated just a short drive north of Chicago. With adrenaline-pumping roller coasters, family-friendly rides, and a water park, it’s a fantastic day trip for families and adventure lovers alike.

Check out our video on Six Flags Fright Fest here.

Route 66 — Start Your Road Trip in Chicago

The image shows a white stencil of the iconic Historic Route 66 shield painted on dark asphalt. The bold black letters spell "Historic Route 66," symbolizing the famous American highway that stretches across multiple states. The contrast between the white paint and the black pavement highlights the historic significance and nostalgic feel of this legendary roadway.

One of the most iconic road trips in America starts right here in Chicago. Route 66 offers a nostalgic drive through charming small towns and historic landmarks. Whether you’re planning a cross-country journey or just taking a short trip down memory lane, it’s a hidden treasure that shouldn’t be overlooked.

Check out our trip on Route 66 here. It was one of the best road trips we’ve ever taken, and what kicked off wanting to build this page of ours!

Discover More Hidden Gems

From secret gardens tucked away in the city to quirky museums, there’s no shortage of things to do in Chicago that many people don’t know about. These hidden gems add an extra layer of charm and wonder to an already fascinating city.

Check out the recent ApartmentGuide article we were featured in:

While Chicago has plenty of icons that draw travelers from near and far, true Chicagoans know exactly where to find unique adventures that will help you get to know the real Windy City. Maybe you are looking for a rental house in Chicago to test the waters, or you want to buy a home near the heart of the city, or maybe your goal is to find an apartment overlooking Lake Michigan. Regardless of what you are looking for, these 16 hidden gems in Chicago are bound to make you feel home.

Read the full article here: 16 Hidden Gems in Chicago, IL | ApartmentGuide.com

Book Recommendations*

We pick up as many books as possible to throw in the car when we’re out traveling around. Like we’ve said in the past, we love to pick a direction and go. Sometimes we’ll drive 10 hours in any random direction. You’ll find a lot of cool stuff this way. But having one of these books will help you find some cool spots you may have missed.

1. Weird Illinois

“Your Travel Guide to Illinois’ Local Legends and Best Kept Secrets.” Part of the Weird U.S. series, this book was one of our first and favorites.

Pick up Weird Illinois here.

Find the rest of the Weird U.S. books here.

2. Oddball Illinois

“A Guide to 450 Really Strange Places.” Another one of our favorites, and again part of the larger Oddball series. We own a copy of each of the states around us here in Illinois. A little more family friendly.

You can pick up the Illinois edition here.

Other versions available:
Oddball Wisconsin
Oddball Iowa
Oddball Minnesota
Oddball Michigan

3. Midwest Road Trip Adventures

“Exploring America’s Heartland, One Scenic Drive at a Time; Road Trip Book and Unique Travel Destinations.” Another great Midwest road trip book.

Check it out here.

4. Midwest Road Trip Adventures

We picked this up from the last Travel and Adventure Show here in Chicago, and glad we did. It’s a fun book with more ideas and stories written by several authors.

You can pick it up here.

“Midwest Road Trip Adventures takes travelers along some of the most storied highways and byways in this unique and spectacular region of the United States. There’s so much more to the Midwest than you might have imagined, so let our authors guide you on your journey through America’s heartland.”

5. Secret Chicago

One last one, Secret Chicago. This is again part of a larger series of books, so there may be one closer to you. “A Guide to the Weird, Wonderful, and Obscure”

Pick up the Chicago version here.

Find the rest of the series here.

* All of these links are Amazon Affiliates, and help us in a small way find and create new content. We truly appreciate any support. If any of these books seem like something you’d like to check out, that’d be awesome. We own the ones I’ve highlighted (and a lot more), and love them.

Frequently Asked Questions

What are the best hidden gems in Chicago? Some of our favorites include Ricobene’s for the best sandwich in the city, the Volo Auto Museum just outside the city, the start of Route 66, and the lesser known neighborhoods on the south and west sides that most tourists never explore.

What is there to do near Chicago that most tourists don’t know about? The suburbs around Chicago are packed with underrated destinations. The Volo Auto Museum, Six Flags Great America, the Illinois stretch of Route 66, Cave of the Mounds in Wisconsin, and the Mid-Continent Railway Museum are all within a few hours and rarely overcrowded.

Is the Volo Auto Museum worth visiting? Yes, absolutely. It is one of the most unique museums in the Midwest and great for all ages. Budget at least two to three hours and bring your camera.

What is the best day trip from Chicago? It depends on what you are into. For car lovers it is the Volo Museum. For history buffs it is the Route 66 corridor through Springfield. For families it is Six Flags or Cave of the Mounds in Wisconsin. We have guides for all of them on the site.

Keep Exploring

There is no shortage of hidden gems around Chicago and across the Midwest. We add new destinations regularly so bookmark this page and check back often.

And if you want the best finds delivered straight to your inbox, sign up for our upcoming monthly newsletter.

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