Outdoor Date Ideas in Wrigleyville

After a long year of COVID-19 cooping us up for as long as we can manage, good weather and lake days are on the horizon. We can bet you’re anxious to get outside and enjoy that fresh air with your honey, and Wrigleyville has all the options to take dinner and drinks to a whole ‘nother level. So, if you’re looking to impress a first date or just get out for date night, we’ve got your back with a few outdoor date ideas around Wrigleyville (and you might just get to support some local businesses along the way!).

Try a local, craft beer.

First off, dinner and drinks – we know it’s the ultimate cliché – but Wrigleyville is home to amazing local brews and food that will have your date asking you to plan another. After all, there’s nothing better than sitting on an outdoor patio on a summer night “cheers–ing” with the perfect, crisp craft beer.

Sheffield’s Beer and Wine Garden’s patio is the perfect place to settle into a first date or provide the casual, non-awkward atmosphere for your new significant other to meet your friends for the first time. With more than 19 beers on draft, you have a plethora of options to choose from.

Or try a more organic option with Uncommon Ground Lakeview, home of Greenstar Brewery – the first organic brewery in Illinois. Between their 12 amazing original brews, you may just have to try them all and get an Uber home!

Get a takeout picnic and head to the lake.

There are few things in this world that are better than relaxing at Lake Michigan in the summertime. If you don’t want or have time to pack a picnic, you can have a beautiful buffet of arrangements from restaurants in Wrigley. We suggest grabbing handheld arepas from Bolivar and Lincoln, splitting a sandwich from Lucky’s Sandwich Company and then topping it off with to-go margaritas from Big Star.

Enjoy the sunshine and one another with good food! If it rains, throw down a blanket on your living room floor, and you’re good to go.

Wine and dine on Sheffield.

While you can’t go to the vineyards of Italy right now, Figo Wine Bar can get you pretty close. With sommelier selected wine and in–house made pasta, they’re the perfect place to have a romantic date night on their outdoor sidewalk cafe.

Additionally, Dine Out on Sheffield will start on Fridays in May, so more seating means more chances for wine!

Go to a Cubs Game, duh.

We know this one’s a given in Wrigley, but who would we be if we didn’t put it on here? Plan ahead to grab some tickets and watch a Cubs game! Enjoy the company of each other and get absorbed in the fun and energetic atmosphere of the crowd. Then, end your date by sharing wings and beer at Murphy’s Bleachers. After all, there’s nothing like game day at Wrigley.

Craft cocktails are where it’s at.

Okay, maybe beer isn’t your thing – I get it, give me a Moscow Mule and my heart soars – or you just want to switch it up. Either way Happy Camper and Bites Asian Kitchen + Bar have cocktails (and awesome outdoor seating!) that will have your taste buds wanting more.

If you’re looking to have a realllll good time, take a sip of the Trailer Park Queen from Happy Camper or a Boozy Bubble Tea from Bites Asian Kitchen + Bar. (Hint: Plan a weeknight date and hit up Bites’ happy hour from 5-6:30 on Monday-Friday!).

Grab an ice cream cone and take a stroll.

We know everyone enjoys a good coffee date, but what about cooling down with ice cream on a hot day with a walk to the lake, Wrigley field, or a nearby park. Whether it’s an ‘Original Recipe’ flavor from Kilwins or the beloved Brambleberry Crisp from Jeni’s Ice Cream, this cute and inexpensive option makes an ideal first date! To break the ice, make it a game, grab a few scoops from each and rate the best one.

Sit and sip on a rooftop.

Now, if you want to get a tan in the afternoon or enjoy the evening breeze, Wrigleyville has some amazing rooftops to grab a drink, a bite, or just have great conversation with each other. You’ll find great outdoor seating for any type of date at Vines on Clark, Deuce’s Major League Bar or Budweiser Brickhouse Tavern!