Chicago Pickle Fest & 4 More Chicago Plans This Week

Five hand-picked things to do this weekend — Wrigleyville pickle-everything chaos, Afghan Whigs at Metro, bluegrass in Lincoln Square, plus Mother's Day gospel brunch and a sunrise charity run on the Lakefront.

By Raj Singh · Published May 9, 2026.

Saturday in Chicago, 73 and overcast — the kind of mild, no-commitment weather that makes the city's calendar feel infinite. Wrigleyville is hosting an entire bar crawl built around pickles. Metro is throwing a 40-year anniversary party for the Afghan Whigs. Old Town School has a bluegrass listening-room show at family-friendly hours. And tomorrow is Mother's Day with two big options: gospel brunch at House of Blues, or a sunrise charity run down the Lakefront Trail. Pick a lane.

SATURDAY, MAY 9

Chicago Pickle Fest @ Wrigleyville bars

A neighborhood-wide bar crawl built around a single, deeply unserious idea — pickle everything. Pickle martinis, pickle margaritas, pickle-back shots, pickle-glazed wings, fried pickles by the basket. It's the kind of event Chicago is weirdly perfect for: a citywide commitment to a bit, run with full venue cooperation across Wrigleyville's loudest stretch of bars.

The vibe is loud, day-drinky, friend-group energy. The crawl format means you can pop in for one round or commit to the whole afternoon. Live bands rotate through the participating bars so the soundtrack changes block to block. Expect long lines at the well-known spots (Sluggers, Murphy's) and breathing room at the under-the-radar ones — that's the strategy. Once you've maxed out on pickle product, walk five minutes to Crosby's Kitchen on Southport for a real meal, or grab a slice at Dimo's Pizza to absorb the brine. Heading north afterward, Sheffield's beer garden in Lakeview has the patio open.

Logistics: starts at noon, runs into the evening. Tickets get you a wristband plus drink and food specials at participating bars. Today's forecast is 73F and overcast with a 4% chance of rain — sweater optional, umbrella unnecessary.

The Afghan Whigs 40th Anniversary Tour with Mercury Rev @ Metro

The Afghan Whigs have been at this for forty years — Greg Dulli's snarl, the soul-haunted swagger, the sense that every song is one bad decision away from a brawl. They're touring on a new album and their 40th anniversary, and they brought Mercury Rev along, which is its own kind of treat. Mercury Rev's Deserter's Songs era still sounds like a 1990s fever dream you almost remembered.

Sweaty, devotional, the kind of show where everyone in the room knows the lyrics to 'Honky's Ladder.' Metro is the venue this is meant to happen in — the floor sloped for sightlines, the upstairs balcony giving you a hawk's-eye view, and a sound system that has been beating up touring bands since 1982. If you've never been: get there early, post up against the railing on the lower level, and ride the wave. Pre-show food: Smoque BBQ on Pulaski is worth the cab. Post-show: Gingerman Tavern across the street has been pouring well drinks for music-show overflow since the Reagan years.

Logistics: 7pm doors, $40-$60 tickets. Running tight — check do312 before you head over. No real parking up here; Red Line to Addison is the move.

Steep Canyon Rangers @ Old Town School of Folk Music

The Steep Canyon Rangers have spent the better part of two decades quietly being one of the most technically clean bluegrass outfits in the country — they're the band Steve Martin tours with when he wants his banjo to actually keep up. Their original material has gotten richer over the years. They're not a tribute act in any direction, just an unusually tight ensemble that happens to operate inside a tradition.

Seated, listening-room respectful — the kind of crowd that claps at the right moments and shushes the talkers in the back row. Old Town School is one of the best-sounding rooms in the city for acoustic music: wood floors, balcony seating, and the kind of audience that has either been to a banjo class or is married to someone who has. You're in Lincoln Square, which is a vastly underrated dinner option. Spacca Napoli is a five-minute walk for wood-fired pizza that holds up against anything in River North. Begyle Brewing on Damen is two stops away if you want a beer after.

Logistics: 5pm show, family-friendly, mid-priced tickets. Brown Line to Western drops you a block from the door. You'll be inside but the walk over is pleasant.

SUNDAY, MAY 10 (MOTHER'S DAY)

World Famous Gospel Brunch @ House of Blues

House of Blues' Sunday Gospel Brunch has been a Chicago Mother's Day institution for years. Live gospel choir, full Southern brunch buffet — fried chicken, collards, biscuits, shrimp and grits, the whole thing — and the kind of room where strangers will be on their feet clapping by the second song. It is genuinely moving even if you're not the demographic. The choir does not phone it in.

Multigenerational, dressed-up-but-not-stiff — families with grandma in the booth and the eight-year-old grandkid stealing biscuits. The first seating (10am) is calmer; the 12:30pm seating gets rowdier as the room warms up. Either works for Mother's Day; book whichever fits the day. House of Blues has its own parking garage attached, which is a Mother's Day miracle since on-street parking on Dearborn is a cruel joke. If your mom wants a flower stop after, Garfield Park Conservatory's spring flower show is twenty minutes away and free. The Riverwalk is two blocks south for a quiet walk.

Logistics: two seatings, 10am and 12:30pm. Mother's Day books up — confirm reservations the night before. Tomorrow's forecast is 62F overcast with zero rain, so the walk to the door is comfortable. Bring a cardigan; the room runs cool early.

Wings for Life World Run @ Lakefront Trail

A globally synchronized run organized by Red Bull's Wings for Life Foundation, with 100% of entry fees going to spinal cord injury research. The format is its own thing: there's no fixed finish line. A 'catcher car' starts behind you 30 minutes after the gun and slowly speeds up — when it passes you, you're done. So you run until you're caught. Same exact start time everywhere on Earth.

Sunrise lakefront energy. Mix of serious runners chasing distance and casual joggers along for the cause. Sub-3-mile finishers are common; the front of the pack regularly clears 20 miles. Costumes and team shirts encouraged. The Lakefront Trail south from DuSable Harbor is the route — flat, fast, scenic, with the skyline behind you. Park at Millennium Garage if you're driving. Post-run, walk three blocks west to Wildberry Pancakes & Cafe in the Aon Center; they open at 7am and the people-watching while you carbo-load is unbeatable.

Logistics: 6am start (yes, really), 11am cutoff. Tomorrow's forecast: 62F at high, but it'll be in the low 50s at gun time — light layers you can shed when you warm up. Zero rain forecast. Charity registration required; spectators free.