In the wise words of that dashing Casanova Walter Sobchak: “Fuck it, Dude.
Let’s go bowling.” This indoor sport where you're encouraged to drink is one of the great fun equalizers we have on this planet.
Luckily, Chicago is brimming with lively bowling options like Diversey River Bowl and Southport Lanes.
Second City is, of course, the granddaddy of comedy-themed date nights, but good times can also be had for fewer dollars (and fewer people from Iowa) at indie comedy venues like the Cornservatory or regular stand-up nights like Timothy O’Toole’s “Comedians You Should Know” (see full list here).Fortunately, comedy shows tend to be pretty cheap dates.Some free advice: Don't spring this one on a first date unless you know you're both high rollers.As the old saying goes, the couple that pets cats together stays together.The entire city of Chicago has a ton of excellent theater.
If you want to keep it in the neighborhoods, the Belmont Theater District in Lakeview is actually the largest in the city if you count by theaters.The lake is kind of an obvious date spot, whether you’re a Chicago native or tourist on Tinder, but that doesn’t make it any less fun.Be sure to hit up Montrose Beach on the North Side, South Shore Beach on the South Side or any of the other fantastic beach spots Chicago has to offer.If you’d rather have a less expensive and quieter (and, some might say, less obnoxious) time, check out the White Sox.If your ideal date involves demonstrating what a stable genius you are, show off your deep base of useless knowledge at one of the many bar trivia nights around town.There’s nothing more fun than Chicago in the late spring and summer -- especially when you get to share it with your main squeeze (or your side piece -- we’re not here to judge).