Grab a stack of singles and head to some of the city’s premier photo booths to document your date progress.Start with live music and live action shots at Schubas before trying your hand at scenario snaps at Quimby’s Bookstore, Beauty Bar, and Empty Bottle before closing out the night at Skylark.

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Start off with some of these top picks for mimosas and Bloody Marys.

If things have been going well, you might even be able to sneak in a midday nap.

Visit Headquarters Beercade or Emporium for arcade games, or Guthries Tavern for good, old-fashioned board games, all with great beer options.

Take a moment to enjoy the beauty that Chicago has to offer, then learn how to start your career as a beekeeper or get your hands dirty at one of Garfield Park’s compost tutorials. Go ahead and visit some of the area's other amazing parks.

Finish off with a nightcap downstairs at modern-day piano lounge Tack Room or the basement-level Punch House, where live DJs and expertly crafted cocktails ensure good vibes.

Get up close and personal while cooking side-by-side at The Chopping Block.

Skip having to spend money on someone you just met with Free Thursdays at the Art Institute of Chicago (you like free stuff, right? Heads you’re taking the CTA, tails you’re taking a cab.

) -- which will both make you seem cultured and give you plenty to talk about. For every decision you need to make, take turns flipping.

Choose from demonstration classes, interactive classes, or wine classes. They've got some of the cheapest vino bottles you’ll find in Chicago, and you’ll be sent home with lots of leftovers.

Day drinking leads to night drinking which leads to 2am burritos at Tony’s or Burrito House.

Tip: Although shisha is quite different from tobacco, make sure your date isn't devoted to maintaining perfectly pink lungs before making any reservations.