Chicago Visitors Guide - 2026
CHICAGO LIKE A LOCAL
2026-01-21 10:19:58
DISCOVER HIDDEN GEMS WITH A CHICAGO GREETER.
Looking to see the city through the eyes of a local? The Chicago Greeter program matches visitors with friendly residents for free walks around the city, diving into everything from must-see sights to best-kept secrets. Now in its 24th year, the program annually hosts more than 3,000 visitors from around the globe, led by a team of more than 90 volunteer Greeters.
One of those Greeters is Jack Warren. A Chicago native, Jack joined the Greeter program in 2023 after spending 10 years as a professional tour guide across the country. His best advice for visitors? Make the time to explore outside downtown.
“Chicago is a cultural powerhouse,” Jack says. “It’s a dense, beautiful metropolis, with so much great history and variety in every neighborhood. Get on the ‘L’ and try some different places.”
Here are some of Jack’s favorite spots and hidden gems throughout Chicago’s vibrant neighborhoods, downtown, and beyond.
ROOFTOP BARS WITH A VIEW
The Up Room at the top of The Robey hotel in the heart of Wicker Park has the best view of the city.
The J. Parker rooftop at the Hotel Lincoln is also spectacular. It overlooks Lincoln Park and Lake Michigan.
COOLEST CONCERT VENUE
Thalia Hall in Pilsen. It was previously a Bohemian gathering spot and now hosts some of the best concerts in the city.
TOP MUSEUMS
The Driehaus Museum near The Magnificent Mile. Chicago came up during the Gilded Age, and this historic home is a showcase of that.
The Griffin Museum of Science and Industry in Hyde Park. Highlights include a captured World War II German submarine, an immersive coal mine experience, and one of the largest model train sets in the world.
MOST UNIQUE BREWERY
Whiner Beer Company in the Back of the Yards. It’s located in a repurposed meatpacking facility, which was one of Chicago’s founding industries.
BEST STREETS FOR ARCHITECTURE
Hoyne Street in Wicker Park is filled with beer baron mansions and German-inspired architecture.
Woodlawn Avenue in Kenwood is lined with beautiful Italianate homes. Barack Obama’s former residence is also nearby.
WORTH THE TRIP
The Pullman National Historical Park in Pullman. It’s the city’s first National Park Service site and an homage to one of the things that built Chicago — the railroad.
FAVORITE GREEN SPACES
The 606 is a great demonstration of how the city is taking our industrial past and turning it into something greener and more pedestrian friendly. The elevated trail spans from Bucktown to Humboldt Park.
Wooded Island in Jackson Park, with its Japanese garden. It’s a relic of the World’s Columbian Exposition of 1893 that was held here.
BEST BEACHES
Montrose Beach in Uptown or Osterman Beach near Edgewater are both less crowded and offer large beaches.
HIDDEN GEM INTERIORS
The Elks National Memorial in Lakeview. It has one of the most beautiful interiors, and you don’t expect it at all when just walking by.
Hutchinson Commons at The University of Chicago in Hyde Park. The cafeteria’s design is inspired by England’s University of Oxford, and it’s open to the public.
BEST SPOT FOR A DRINK
The Glunz Tavern in Old Town. It’s an old German watering hole founded in the 1880s and is one of the oldest taverns in the city.
Want more hidden gems? Schedule a Chicago Greeter tour for your own personalized walk.
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CHICAGO GREETER TOURS
Book a free Chicago Greeter neighborhood tour led by a friendly local volunteer who will share interesting facts and insider tips. Explore important LGBTQ+ history in Northalsted. Learn about influential African American civil rights, music, and arts pioneers in Bronzeville. Discover the stories behind Pilsen’s vibrant murals. Tours customized to your interests can last from two to four hours and are offered in over a dozen languages. Register at least two weeks in advance of your visit to Chicago at chicagogreeter.com.
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