Memorial Day weekend is basically the unofficial start of summer, which means patios, street fests, baseball, cold drinks, BBQ, and at least one person dramatically declaring themselves “the grill master.” Whether you’re hosting the backyard crew, heading to Belmont Sheffield Music Fest, catching the Cubs at Wrigley, marching in the WOOGMS Parade, or just looking for something smoky, saucy, and fun to do, Lakeview East and Wrigleyville have the weekend covered. From BBQ and wings to festival bites, party trays, and classic neighborhood events, consider this your guide to kicking off summer without overthinking it.

The best way to celebrate the official kick off to summer? How about at a Chicago street festival that has two stages, dozens of food vendors, cold drinks, desserts like Italian ice and gelato, and dancing and singing?! The Belmont Sheffield Music Festival is one of the very first Chicago Street Fests of the year, and we are kicking it off with a bang. Join us at the corner of Belmont and Sheffield, right by the Belmont L Stop, for a three day festival of music, dining, and fun! This years headliners include Chicago favorites Rod Tuffcurls and the Bench Press, Trippin Billies, and Hello Weekend! View the full weekend line up, and details about the fest, here!

Smoke Daddy Wrigleyville

Smoke Daddy is an easy go-to for classic BBQ in Wrigleyville, with slow-smoked meats, hearty sides, and catering options available for pickup or delivery. Their menu leans into all the good stuff: smoked meats, ribs, brisket, pulled pork, BBQ wings, sandwiches, and crowd-friendly sides that make planning a party a whole lot easier. Basically, if your event needs something smoky and satisfying, Daddy’s got you.

Old Crow Smokehouse

Old Crow Smokehouse brings the full Wrigleyville BBQ experience, with smoked brisket, pulled pork, ribs, wings, hearty sides, and plenty of big-group energy. Their catering menu includes BBQ packages, appetizer platters, smoked wings, pulled pork egg rolls, mac and cheese, baked beans, coleslaw, and more, making it a solid pick for everything from corporate lunches to backyard parties. Bonus: it comes with that “steps from Wrigley Field” energy baked right in.

Milt’s Barbecue for the Perplexed

Milt’s is a neighborhood favorite for kosher BBQ, serving up smoked meats, wings, brisket, BBQ chicken nachos, brisket empanadas, sauces, sides, and catering options for groups. Their catering menu includes trays and party-friendly items like wings, pickles, pretzel bites, brisket chili, and more, which makes them a great option when you want something hearty, flavorful, and a little different from the usual party spread.

Sheffield’s Beer Garden

Sheffield’s brings the beer garden, patio, and BBQ energy all in one very Lakeview package. Their menus include BBQ favorites like pulled pork, brisket, ribs, smoked chicken, BBQ flatbread, and more, and they do offer catering with advance notice. Translation: if your gathering needs smoky comfort food, cold drinks, and “we accidentally stayed all afternoon” energy, Sheffield’s belongs on the list.

ROCKS Lakeview

Rock’s Lakeview makes group ordering easy with a catering menu built for casual, crowd-pleasing comfort food. Their catering options are great for the kind of gatherings where people want something familiar, filling, and easy to share, from office lunches and graduation parties to Cubs watch parties and neighborhood get-togethers. Think wings, sliders, wraps, salads, mac and cheese, and plenty of hearty bites that can keep a group happy without overcomplicating the plan. It’s not traditional BBQ, but it absolutely belongs in the saucy, snacky, game-day-friendly category. Easy, reliable, and very Lakeview.

Output Lounge & Sports Bar

Output is for the wing loyalists. Known for its no-fuss sports bar vibe and seriously craveable wings, this is a strong option when you want the food to be casual, filling, and gone within five minutes of hitting the table. Perfect for game days, casual gatherings, and anyone who believes wings deserve their own food group.

WOOGMS Memorial Day Parade
Monday, May 25 at 11 AM | Wellington & Pine Grove

Lakeview’s longest-running neighborhood tradition is back! Since 1963, the WOOGMS Parade has brought families, neighbors, strollers, scooters, flags, and full-on community charm to the streets with its famous motto: “Everybody Marches and Nobody Watches.” Join the Wellington-Oakdale Old Glory Marching Society for a cheerful Memorial Day march through the neighborhood, featuring the Jesse White Tumblers and plenty of classic Lakeview spirit. Meet at Wellington and Pine Grove at 11 AM and jump right in.

Memorial Day Brunch at El Mariachi Tequila Bar and Grill

Celebrate Memorial Day with bottomless brunch! For just $19.99 enjoy bottomless mimosas with the purchase of an entrée. Craving something stronger? Upgrade to bottomless margaritas for just $10 more! Brunch will be served from 10 am to 3 pm, then dinner will be going on till 10 pm. Sip on $7 house lime margaritas all day!

Open Patio Brunch at Barcocina

Take full advantage of the gorgeous weather this weekend by taking your leisure time outside. Barcocina on Sheffield has an amazing patio with all the space you could need whether you’re with family, friends, or otherwise. The brunch menu here leaves nothing to be desired from cheeseburger tacos, chilaquiles, to birria tostadas, and it’s all delicious.

Celebrate Memorial Day at Drew’s on Halsted

Come celebrate the long weekend with good food and good company. Drew’s on Halsted is your go-to spot for Memorial Day specials and dining. Their happy hour runs 4 pm—6 pm and features appetizers, beer, wine, house cocktails, old-fashioned drinks, palomas, sangrias, and new signature drinks for $9!

Memorial Day Hours at George St Pub

This iconic neighborhood staple on Halsted is down for the party this Memorial Day. Alongside their typical, delicious, bar fare, they’re offering $11.95 wings & $5 draft beers in honor of the occasion. They’ll be serving it all 11 am to 11 pm.