Festivals & special events, Free & cheap, Music
Chicago Blues Festival
June 5 – 8, 2025 Free admission • Millennium Park and beyond A legendary Chicago event since 1984, the Chicago Blues Festival is the world’s…
Articles
Festivals & special events, Music
Lollapalooza Chicago guide: lineup, schedule, tickets, and more
July 31 – Aug. 3, 2025 Grant Park Each year, thousands of fans travel from around the world to experience Lollapalooza in Chicago. Those lucky…
Food & drink, Parks & outdoors
Waterfront restaurants on the lake in Chicago
Chicago is known for its famous skyline and urban neighborhoods, but it’s also right next to one of the largest lakes in the country. That…
Family, Itineraries
30+ kid-friendly things to do in Chicago
Chicago is a place where kids’ imaginations soar, with endless things to do and see around every corner. From hands-on museums and sprawling parks to…
Festivals & special events, Free & cheap, Music
Chicago Jazz Festival
Aug. 28 – 31, 2025 Free admission • Millennium Park The oldest of Chicago’s free lakefront music festivals, the Chicago Jazz Festival boasts an incredibly…
Festivals & special events, Food & drink
Taste of Chicago
Sept. 5 – 7, 2025 Free admission • Grant Park and citywide The 45th annual Taste of Chicago is bringing some of the city’s most…
Free & cheap, Museums & art
Free museum days in Chicago
Experience Chicago’s award-winning museums without spending a dime. Check out our ever-growing list of Chicago free museum days in 2025, plus a few museums that…
LGBTQ+
LGBTQ+ nightlife in Chicago: gay and lesbian bars, clubs, and more
Chicago’s nightlife is a lot like the city itself — inclusive, diverse, and welcoming to all. It’s also a whole lot of fun. Our gay…
Festivals & special events, Food & drink, Music
Windy City Smokeout
July 10 – 13, 2025 United Center parking lot Country music, barbecue, and craft beer — it’s hard to think of a better way to…
Articles, Bucket list, Itineraries, Parks & outdoors
Things to do in Chicago in the spring
What’s spring like in Chicago? Tulips bloom along iconic Michigan Avenue, cherry blossoms pop up in Jackson Park, and city parks begin to overflow with…
Articles, Hotels
Chicago hotels with rooftop bars
Chicago is a city known for its stunning skyline, and one of the best ways to enjoy it is from the city’s many rooftop bars.…
Dining, Holidays
35+ romantic spots for Valentine’s Day dinner in Chicago
The biggest date night of the year is coming up, and the city’s restaurants are pulling out all the stops so you and your date…
Explore Chicago hotels, flights, deals, and more
Plan your trip
