11am: Lula Cafe
Start with one of the city’s top brunches (try the tofu-and-veggie scramble with ginger-miso sauce or grab a breakfast burrito) at Lula Cafe. Get there early to snag a seat on the patio for a view of the Illinois Centennial Monument.
1pm: Wolfbait & B-Girls
Buy handmade souvenirs at Wolfbait & B-Girls or venture over to City Lit for a great selection of books.
7pm: Yusho and Lost Lake
Order some steaming ramen from the Japanese grill Yusho. Then bring on the vacation vibes with a postdinner drink at the tiki bar Lost Lake.
Grab a nightcap at OSB, a.k.a. Off Site Bar, at the inn and Michelin-star rated restaurant Longman & Eagle. Then retire to one of six totally hip and adorable rooms upstairs.
Begin early with a heart-starting cup of coffee from Intelligentsia (2642 N Milwaukee Ave; 773-945-1690, intelligentsiacoffee.com), then head to Bang Bang Pie & Biscuits off the California Blue Line for to-die-for fluffy biscuits at one of the picnic tables.
1pm: Parson's Chicken & Fish
Take a walk and hit the patio at Parson’s Chicken & Fish for a Negroni Slushy and fried chicken. After a round of ping-pong, hop on a Divvy bike just outside to cycle back into the center of the ’hood.
5pm: Emporium Logan Square, The Whistler, Revolution Brewing
A quintessential night in Logan Square includes pinball and snacks from the indoor food truck at Emporium Logan Square, followed by an elaborate cocktail on the Whistler’s patio (2421 N Milwaukee Ave; 773-227-3530, whistlerchicago.com). For an experience that’s a little more laid-back, head next door to Revolution Brewing (2323 N Milwaukee Ave; 773-227-2739, revbrew.com) for some local beers.
11am: Logan Square Farmers Market
Recover with some shopping (produce, flowers and even hot sandwiches) at the Logan Square Farmers Market.
1pm: Logan Theatre
Catch a flick at the Logan Theatre. The cozy indie theater has a full bar, too, if you need a little hair of the dog.
4:30pm Fleur and Shop 1021
Hit Fleur for plants, or get great gift ideas at Shop 1021 (2650 N Milwaukee; 773-235-1021, shop1021.com).
Toss a Frisbee or lounge in the grass at Palmer Square Park (2200 N Kedzie Ave) to end the day in one of the city’s coolest places.