Free & cheap
10 free things to do in Chicago this May 2026
This month in Chicago, explore the city’s oldest outdoor market, admire iconic works in one of the world’s top art museums, and take an outdoor…
National Museum of Mexican Art in Pilsen
Chicago Like a Local blog
Unique perspectives on the city from the people who live here.
News & Awards
Chicago voted Best Big City in the U.S. for the ninth year in a row
Chicago has once again earned the title of Best Big City in the U.S. in the Condé Nast Traveler Readers’ Choice Awards for a historic ninth consecutive year.
Latest Posts
Neighborhoods, Tours & attractions
How to spend 24 hours in Chicago’s Hyde Park
The historic, tree-lined streets of Chicago’s storied Hyde Park neighborhood are filled with Gothic architecture, cultural landmarks, and a welcoming energy that gives it a…
Blog, Special events
50+ things to do in Chicago this May 2026
May is a jam-packed month in Chicago — summer is on the horizon, tulips are blooming all over the city, and weekends fill up with…
Arts, culture & entertainment, Blog, Special events
How to celebrate Asian American and Pacific Islander Heritage Month 2026 in Chicago
AAPI Heritage Month Events in Chicago This May, Chicago will celebrate the city’s diverse AAPI communities. Here are a few ways to participate: Admire never-before-seen…
Blog, Sports & recreation
Chicago Fire FC players share their favorite things to do in the city
In 1871, the Great Chicago Fire swept through the city and destroyed much of downtown. Yet Chicago rose from the ashes, building back bigger and…
The 77: A City of Neighborhoods
THE 77 – CHICAGO TV TRAVEL SERIES Embark on a journey through the diverse and complicated tapestry of Chicago’s neighborhoods as we unveil “The 77:…
Festivals
Chicago street festivals: your ultimate summer guide
Summer in Chicago just wouldn’t feel complete without the city’s beloved street festivals, which include an eclectic array of neighborhood celebrations across the city. These…
Blog, Theater & dance
Chicago cabaret 101: venues, events, and tips for catching a great show
If you’ve never been to a cabaret show, Chicago is a great place to start. With a 100-plus year history rooted in the city’s early…
Arts, culture & entertainment, Blog
A Chicago summer bucket list for culture lovers
Chicago’s summer event calendar is overflowing with cultural happenings. From groundbreaking art exhibits to exciting theatrical premieres, there’s truly something for everyone to enjoy. Check…
Architecture & history, Blog
The history of Route 66 in Chicago
For a century, the illustrious history of Route 66 has captured the American imagination. More than a highway, the so-called “Mother Road” is an open‑road…
Blog, Dining
James Beard Awards 2026: full list of Chicago nominees
The annual James Beard Awards recognize the best and the brightest of the nation’s dining scene. These prestigious accolades honor not only chefs and restaurants…
Arts, culture & entertainment, Blog
Top international art fair EXPO CHICAGO returns to Navy Pier this spring
EXPO CHICAGO Contemporary Art Fair returns to lakefront Navy Pier from April 9 – 12, 2026 with an exciting roster of 130 leading galleries from around…
Architecture & history, Blog
Black history tours in Chicago: food, history, culture and more
Black history tours of Chicago offer an engaging journey through the city’s rich African American culture. Embark on an in-depth exploration of influential neighborhoods like…
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