Chicago — week of Monday, August 3, 2026

First edition. Every week: complete date plans — times, order, links, budget, backup — plus what to book before it sells out. This week's spread: four blocks of Wells Street doing all the work for you, a Pilsen speakeasy-to-Bib-Gourmand night, and golden hour on the 606. August is fest season; the radar is stacked and almost everything on it is free.

Everything happening 5

Tuesday, Aug 11

Millennium Park Summer Film Series her thing ✓ Tue Aug 11 & 18 · Free Free movies at Pritzker Pavilion, 6:30 PM — Aug 11 is The Devil Wears Prada, Aug 18 is Sinners.via City of Chicago

Saturday, Aug 15

Chicago Air and Water Show her thing ✓ Aug 15–16 · Free Thunderbirds over the lakefront — claim blanket space at North Avenue Beach by mid-morning.via Choose Chicago

Thursday, Aug 27

Chicago House Music Festival her thing ✓ Aug 27–30 · Free Four free days of DJ sets in the genre's birthplace, at Millennium Park and the Chicago Cultural Center.via Choose Chicago

Friday, Aug 28

Taste of Greektown her thing ✓ Aug 28–30 · Free entry (suggested donation) Live music, dancing, and Halsted Street's restaurants cooking outside — Fri 4-10 PM, Sat-Sun 11 AM-10 PM.via Greektown Chicago

Saturday, Aug 29

Bucktown Arts Fest her thing ✓ Aug 29–30 · Free 39th-year neighborhood art fair at Holstein Park — a low-pressure wander-and-talk date.via Bucktown Arts Fest

Planned dates

The Move of the Week

The Wells Street Classic

first-date

Cost: ~$180–280 for two

her kind of night ✓ North Side

6:00 PM Dinner at Kayao, 1252 N Wells — Peruvian-Nikkei — reserve
7:30 PM Two blocks up to Jeni's for a scoop
Showtime Doors at The Second City, 1616 N Wells — showtimes vary by night — Fri & Sat run 6:30 and 9:30 PM, not 8; buy for your night and build dinner around your curtain
10:00 PM Post-show drink back on Wells if the night's going well

Weather backup: Everything's indoors and the walks are under five minutes. This one doesn't check the forecast.

Pilsen After Dark

impressive

Cost: ~$150–220 for two

her kind of night ✓ West Loop & Pilsen

6:00 PM Cocktails at The Alderman inside Pilsen Yards — sixteen seats — reserve ahead, especially Fri/Sat
7:00 PM Ten-minute walk to dinner at HaiSous — closed Mon–Tue; book Wed–Sun
8:30 PM Paletas on 18th Street and a wander down the mural corridor — a 15-minute walk west along the mural corridor — paleterias close around 9, don't linger over the check

Weather backup: Pouring? Take the paletas to go and finish the night back at The Alderman's bar.

Logan Square Golden Hour

active

Cost: ~$110–180 for two

her kind of night ✓ Wicker Park & Logan Square

6:00 PM Mediterranean small plates at Elia
7:30 PM Walk the 606 from the Walsh Park access point — golden into blue hour
8:30 PM Duckpin bowling and boozy milkshakes at Pink Squirrel — two duckpin lanes only — book the lane ahead or expect a wait; short rideshare

Weather backup: Skip the 606 and open with bowling — Elia to Pink Squirrel, fully indoors.

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