Entertainment, Free & cheap
10 free things to do in Chicago this April
There’s never a shortage of things to do in Chicago — and luckily, many of those things are free. Every month brings a fresh batch…
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…
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…
Holidays
Memorial Day weekend in Chicago
Memorial Day weekend marks the official start of summer in Chicago, and the city knows how to celebrate. Each year, Chicago comes to life with…
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…
Festivals & special events, Music
Top summer music festivals in Chicago
Music lives large in Chicago, from our neighborhood streets and historic venues to downtown parks and our iconic lakefront. And Chicago’s iconic festival season brings…
Parks & outdoors
Explore The 606 elevated park and trail in Chicago
An abandoned railway has been given new life on Chicago’s northwest side. The 606 is a 2.7-mile elevated park and trail built on what was…
Holidays
St. Patrick’s Day in Chicago
There’s nothing quite like St. Patrick’s Day in Chicago, when Irish taverns fill with revelers, cultural celebrations pop up in every corner of the city,…
Architecture & history, Festivals & special events
Chicago Architecture Biennial
Sept. 12, 2025 – Feb. 28, 2026 Free admission • Chicago Cultural Center & partner locations Experience the future of architecture at the 10th annual…
Bucket list
Things to do in Chicago in the winter
Winter is one of the most magical times of the year in Chicago, when snow gives the city an added sparkle. Embrace the season and…
Explore Chicago hotels, flights, deals, and more
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