Everyone knows about Millennium Park, Navy Pier and the Magnificent Mile and while they’re all iconic for a reason, they’re only the beginning of what Chicago has to offer.
If you were to ask locals where they spend their weekends, you’ll hear about colorful neighborhoods, tucked-away cocktail bars, a diverse food scene, independent bookstores and waterfront activities. If you’re looking for the real Chicago, here are recommendations to some of the city’s best hidden gems that are perfect for first-time visitors, returning travelers or lifelong-Chicagoans.
If you really want to discover Chicago’s hidden germs, start with the city’s neighborhoods, and there’s no better way to explore them than a guided food tour through the city.
At Chicago Food & City Tours, we take you beyond the typical tourist attractions and into neighborhoods where Chicago’s food scene comes alive. Along the way, you’ll enjoy delicious local specialties, learn the history behind each neighborhood and discover restaurants, bakeries and hidden spots you might never find on your own.
Choose the food tour that's right for you:
Whether you're visiting Chicago for the first time or have lived here for years, our tours offer a fresh perspective on the city. They're also a memorable choice for corporate events, birthday parties, family gatherings, bachelor and bachelorette celebrations and entertaining out-of-town guests.
One of the biggest mistakes you can make is staying downtown for your entire trip. Chicago is a city of neighborhoods, each with its own personality, architecture and food which is why we recommend you take the time to pick a neighborhood and explore it in-depth during your stay.
To help you get started, you can’t go wrong with any of these neighborhoods filled with Chicago’s best hidden gems:
With so many different neighborhoods in Chicago, there is something for everyone.
You may not realize there is another city beneath downtown Chicago. The Chicago Pedway is a network of underground tunnels and indoor walkways connecting office buildings, train stations, shopping centers and public spaces. Navigate a quirky 5-mile underground labyrinth to discover glowing Victorian stained-glass exhibits, hidden subterranean cafes, and secret portals into grand architectural landmarks.
On hot summer afternoons or cold winter days, it's a great way to explore downtown from a completely different perspective.
While the Garfield Park Conservatory is often overlooked by Lincoln Park Conservatory it is still one of Chicago’s most beautiful indoor escapes. You’ll find massive tropical plants, desert landscapes, seasonal flower displays and peaceful walking paths.
Best of all? Admission is free, although reservations may be required during peak hours.
Chicago’s Prohibition-era history lives on in a collection of creative speakeasies that are tucked behind unmarked doors and unexpected entrances.
A few of our favorites include:
While we all love shopping on the famous Michigan Avenue you can also explore some of Chicago’s locally owned shops to support small businesses.
Our favorites include:
While Chicago has many impressive museums, some of the best attractions can be found outside, painted across entire buildings in the city. We recommend neighborhoods like Pilsen, Logan Square and Wicker Park.
Don’t miss out on:
If you ask a local for the best skyline view, they won’t mention the Skydeck in the Willis Tower. Instead, they’ll recommend Promontory Point in Hyde Park which is a peaceful lake peninsula that has breathtaking panoramic views during sunset.
While Chicago has many well-known museums such as the Art Institute and Field Museum, there are also many smaller museums that are just as good.
We recommend:
In the warmer months you can find there is something to celebrate every weekend in Chicago. From neighborhood food festivals to live music, craft markets and cultural celebrations, these events offer an authentic slice of city life and get you away from the popular attractions.
Whether you’re a lifelong music fan or just looking for a fun night out, catching a live show is one of the true Chicago experiences you can have.
Our favorites spots include:
Looking for some Chicago history? Did you know that The Green Mill was once a frequented stop by Al Capone?
One of the most unique ways to experience Chicago is from the water. We recommend in the warmer months to rent a kayak and paddle through the heart of downtown. There are also many guided tours available for beginners. But, if you’d rather not get into the water you can also walk the Chicago Riverwalk for the same views and access to riverfront restaurants.
Experience Chicago Beyond the Guidebooks
While Chicago’s biggest attractions are worth seeing, so are the small hidden gems you can find along the way. Whether you're tasting handmade dumplings in Chinatown, exploring the murals of Pilsen, wandering Wicker Park, or discovering a family-owned bakery you've never heard of, Chicago has something for everyone.
If you want an easy way to uncover these hidden gems while enjoying some of the city's best food, join one of our Chicago Food & City Tours. You'll experience the neighborhoods locals love, hear the stories behind the restaurants and leave with plenty of recommendations for the rest of your visit.
See our tour calendar for more availability.
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