1. Live at Lolla

In 2013, Lollapalooza first-timers Kendrick Lamar and Lana Del Rey were the final names on the festival poster’s third and fifth rows. Ten years later, they’re both headlining acts. The rest of this weekend’s lineup hardly needs an introduction, but there’s superstars and rising stars among the 170+ artists at the Grant Park stages. Aug. 3–6. lollapalooza.com

2. Bear Witness

An annual Soldier Field tradition, the Chicago Bears Family Fest has inflatable games and navy blue face paint to spare. Stick around after watching the team’s first in-stadium practice to see if you can score an autograph. Aug. 6. chicagotap.org

3. A Real Thriller

The James M. Nederlander Theatre will turn into ’80s MTV with four-times Tony-winning musical MJ: the Musical. The production begins its national tour with a month’s worth of Chicago shows, each containing about 40 songs from the King of Pop. Aug. 1–Sept. 2. broadwayinchicago.com

4. Asian Tradition

Say nǐ hǎo, konnichiwa, or namaste to the three-day Destination Asia Festival. The Morton Arboretum event includes a floating lantern display, a bonsai exhibit, and a slate of cultural demonstrations. Aug. 4–6. mortonarb.org

5. Assent to Ascent

Speed-climbing events are sometimes decided by milliseconds, making the North Face Climb Festival a literal and figurative cliffhanger. If you’re brave enough, enter the competition and stare up a 55-foot wall over a pool of water. If not, there’s friendlier onsite climbing for all attendees. Aug. 4–5. climbfestival.com