Chicagoans once held two truths to be self-evident: the Cubs were baseball’s eternal lovable losers, and the general tenor of Wrigleyville, the team’s home ’hood, was boozed-up and unrepentantly lowbrow. Then in 2016, the Cubbies clinched the World Series – and sticky-floored Wrigleyville began smartening up, welcoming swanky new hotels, cocktail bars and restaurants worth hitting even after the season ends.
The area’s ongoing redevelopment has proven divisive. Detractors lament rising rents and a perceived erasure of local color, while many who formerly felt shut out of the neighborhood, from families to foodies to the sports-averse, consider its broadened appeal a win. Decide for yourself whether the revamped Wrigleyville makes the cut with our guide to its new lineup of hotspots.
For Cubs fans who crave a more memorable gameday meal than mega-chain fast food (not to mention fine-dining hounds who previously wrote off the neighborhood wholesale), one of Wrigleyville’s most welcome recent developments is the establishment of a restaurant scene helmed by some of Chicago’s top chefs.
Mordecai is housed within stylish and sprawling Hotel Zachary, just opposite Wrigley Field. Whether or not you’ll be heading across the street to enjoy the national pastime, you can dig into playful riffs on all-American classics in the restaurant’s first-floor dining room: think funky goat bratwurst and beignets dressed in popped sorghum and candied peanut “crackerjack.” Upstairs, the bar and its outdoor terrace offer vintage whiskeys and an eyeful of stadium views. Down the block at Dutch & Doc’s, marble-topped tables, high ceilings and massive windows (the latter of which overlook Wrigley’s iconic marquee) create an airiness brought into pleasing relief by hearty house fare like steak, roasted chicken and butterscotch pudding.
Hitting closer to the cheap and cheerful end of the spectrum is the first outpost of Wicker Park favorite Big Star. This come-as-you-are Mexican street food-inspired spot from local celeb chef Paul Kahan scores points for single-barrel whiskey, honky tonk tunes and tacos stuffed with fancy fixings like mole poblano and sesame crema-topped chicken thighs.
Cocktails and local brews take the lead
Wrigleyville has long had rowdy watering holes in spades, but a trio of new bars aims for drinkers whose style is more sip and savor than shots-shots-shots (no judgment).
In keeping with the playful nods to baseball that underscore the design at the boutique-y Wheelhouse Hotel above it, speakeasy-style subterranean lounge Tinker to Evers takes its name from a pair of Cubs whose fielding prowess was immortalized in a 1910 poem. Quaint portraits of the eponymous players and their contemporaries look out over a dimly lit room dominated by blue velvet banquettes. The bar pours crafty cocktails as well as amari, eau de vie and a number of other digestifs that make a great finish to the Detroit-style pan pizza served upstairs at Union Full Board.
Not to be outdone by its neighbor, the stately lobby bar at Hotel Zachary mixes up classic Manhattans and martinis as well as creative concoctions like the All Sequins Everything, a citrusy sipper featuring sparkling wine, Aperol and strawberry jam. Library tables and armchairs arranged in intimate clusters encourage long chats. For the coziest seat in the house, settle in on the chesterfield that faces the fireplace.
Even the neighborhood suds game gets a tony upgrade at Wrigley-adjacent Lucky Dorr, a modern beer hall and patio featuring 20 handles predominantly dedicated to pours brewed exclusively for the bar by local outfits like Moody Tongue, Whiner and Haymarket. New releases are tapped with ceremony at a weekly Meet the Brewer event.
Little Leaguers welcome
Historically, pub-centric Wrigleyville hasn’t had much to offer wee ones in the way of pre- and post-game entertainment. But a major facet of the neighborhood’s reinvention has been a push to appeal to visitors of all ages, encouraging game-going families to make a day of it rather than hightailing out of dodge the moment the last pitch is thrown.
No spot better epitomizes the area’s new-and-improved family-friendly vibe than Gallagher Way, an erstwhile surface parking lot repurposed as a stadium-side park. On game days, tiny ticket holders can chill on the lawn (or in steamy summer weather, cool off in the splash pad). And whether or not the Cubs are in season, there’s a raft of ongoing programming suitable for all ages, from open-air movie nights and farmers markets to Halloween parties, ice skating, and a holiday-season festival.
In an effort to roll out the welcome mat for little ones on the dining front, restaurants like Dutch & Doc’s and all-day barbeque spot Smoke Daddy offer complimentary kids’ meals. And when it’s time for an indulgent treat, ice cream shop Jeni’s has the goods to please kids and parents alike. Set in a charming space that features bleacher-style seating in homage to its famous neighbor, the Ohio-bred chain scoops out super-inventive flavors that run the gamut from marshmallow cereal milk-flavored Supermoon to adults-only Frosé Sorbet.
Score unique souvenirs
Bear cub-adorned caps, felt pennants and a sea of blue t-shirts: the shopping scene around Wrigleyville tends to be much of a muchness. Not so at newcomer Baseballism. Rather than Cubs-specific gear, the shop deals in unique wares that celebrate a love of the game, no matter your team allegiance – see, for instance, the minimalist backpacks and women’s totes made from buttery glove leather, and the stylish men’s button-downs featuring baseball-themed prints.
How many different permutations of the Cubs hat are possible? That’s the burning question that inspired a whole wall of headgear at Wrigley Field’s slick shop (Answer: too many to count). In addition to two stories of team paraphernalia, the store features interactive photo ops that allow fans to insert themselves into the batter’s box or the outfield. If you’re feeling especially flush, pop next door to Josten’s, the jeweler responsible for the Cubs’ World Series ring. An “Ultimate Fan” version of the diamond-encrusted bauble starts at a cool $1250.
Get more travel inspiration, tips and exclusive offers sent straight to your inbox with our weekly newsletter. Make sure you’re ready for anything with travel insurance from our trusted partners.