The Best Rooftop and Patio Dates in Chicago

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“There’s a three-hour wait for the patio, but we can seat you inside right away.”

On a beautiful day, there’s nothing worse than being confined to the great indoors. Thankfully, al fresco dining and drinking abounds in Chicago this time of year, and with the selection of rooftops, backyards and patios at the city’s disposal, you’re sure to find a two-top in no time.

1) Picnic-style dining:

Parson’s Chicken and Fish

Less than a month after opening, Parson’s has already made a name for itself as a great date spot, and the reason’s clear – that patio. With whitewashed picnic tables that seat up to 250 guests, a bar built from old shipping containers, and a vintage Chevy El Camino chillin’ outside, the mise-en-scène at this place could transform even a painfully awkward date into a total funhouse.

Honorable Mention: Three Aces

2) For an evening in Roma (more or less):

Piccolo Sogno

Picture the most charming Tuscan patio you can imagine, complete with sprawling tables and couples who are way too good looking to realistically eat heaps of hand-cut pasta. Now, picture all of that, but steps from downtown Chicago. Add delicious rustic fare like Marsala-glazed ravioli and wood-roasted duck into the mix, and you’ll have a dinner date that’s sure to give Lady and the Tramp a run for its money.

Honorable Mention: Briciola

3) If there’s room for dessert:

Bang Bang Pie Shop

Full disclosure: Bang Bang’s backyard is my favorite outdoor space in the city, bar none. Enclosed by white-picket fences, a makeshift wall of antique doors, and enough string lights to fill 47 Pinterest boards, every aspect of this patio is simply endearing. The only problem? They close at 7 PM on weekdays and 5 PM on weekends. But while Bang Bang might not be the best spot for a nightcap, it blows everywhere else out of the water on cuteness alone.

Honorable Mention: RM Champagne Salon

4) To see and be seen:

The Dec at deca Restaurant + Bar

Resting atop the Ritz in River North, it’s no surprise that the Dec is already this season’s go-to spot for trendy imbibers. But don’t let your date be distracted by the color-changing, LED-screened walls – this place has some serious cred. And when I say “cred,” I’m clearly talking about the throwback ice-cream cart that trolls past the tables.

Honorable MentionsNoMi Terrace & The J. Parker

5) For playing hooky:

Big Star

Come at a normal time and you can expect to wait two-plus hours at this Wicker-Park staple, but if you’re into the idea of tacos and Tecates on a Wednesday at noon, you and your date can enjoy the quaint rumbling of the Blue Line in (relative) peace. And on the off-chance that you decide to brave the dinner rush, don’t miss the adjacent take-out window, which boasts the same menu as the main space, not to mention first-come-first-serve seating.

Honorable mention: Cedar Hotel