Travel Magazine

9 Things to Do Over Memorial Day Weekend in Chicago

By Urbanmatter Chicago @UMatterChicago

While Memorial Day is primarily about honoring the citizens who’ve made the ultimate sacrifice, it’s also about celebrating our nation and patriotism. Luckily, it’s also a time for warm weather, and many consider it to be summer’s official kick-off.

Appreciate the importance of Memorial Day by watching one the largest parades in the country right here in Chicago, then kick back and enjoy some good ol’ fashioned fun with family and friends throughout the weekend and your day off with these great local specials and events.

Memorial Day Parade and Wreath Laying Ceremony

memorial day weekend chicago

Photo Credit: City of Chicago

Daley Plaza, 50 West Washington Street

On May 27, join others in the streets of downtown as the city honors our nation’s fallen heroes with one of the largest Memorial Day parades in the country. The Wreath Laying Ceremony begins at 11am, then the parade starts at noon down State Street from Lake to Van Buren.

Brando’s Speakeasy Happy Hour

memorial day weekend chicago

Photo Credit: Hedonist / Shedonist

343 South Dearborn Street

On Monday, May 29 from 5pm – 7pm, enjoy $5 Makers Mark Boiler Makers, $4 Bulleit Rye Old Fashioneds, $3 Absolut Moscow Mules, half-off all Revolution beers, $3 flatbreads and small pizzas, and $5 meat and cheese trays at this fun karaoke bar in the South Loop.

Opening Weekend Party at Castaways

memorial day weekend chicago

Photo Credit: Castaways

1603 North Lake Shore Drive

It’s not officially summer until Castaways is open. From May 27 – 29, enjoy live DJ entertainment from 1pm – 7pm, Castaways cocktails, lunch and dinner items, and cabana rentals for up to 12 people at Chicago’s favorite beach house.

Easy Bar Al Fresco Happy Hour

memorial day weekend chicago

Photo Credit: Easy Bar

1944 West Division Street

On Monday, May 29, treat yourself to a half-off-everything happy hour menu from 5pm – 7pm, and $5 margaritas, $2 PBR, and $6 Tecate and Jimador shot until 2am while you relax on this Wicker Park bar’s dog-friendly sidewalk patio.

Al Fresco Dining and Summer Cocktails at Kanela Breakfast Club

memorial day weekend chicago

Photo Credit: Kanela Breakfast Club

From May 26 – 29, enjoy new seasonal cocktails for only $9 at this go-to brunch spot, with names like Cinnamon Toast Brunch, Ginger Paloma, and Tony Danza, while you dine outside at one of their locations in Andersonville, Lakeview, Old Town, Streeterville or Wicker Park.

Memorial Day Weekend at Miller Lite Beer Garden

memorial day weekend chicago

Photo Credit: Navy Pier via Google+

700 East Grand Avenue

From May 26 – 29, head to Navy Pier’s beer garden for live music, unbeatable Lake Michigan views, and a happy hour from 4pm – 6pm that includes $3 Miller Lite, $4 Blue Moon drafts, $6 Smirnoff vodka lemonades, $7 Bacardi Mai Tai, $6 loaded french fries, $4 cheese pizza, and $7 popcorn shrimp basket.

Belmont-Sheffield Music Festival

memorial day weekend chicago

Photo Credit: Lakeview East Chamber of Commerce

3200 North Sheffield Avenue

On May 27 – 28 from 12pm – 10pm, this outdoor festival returns for its 33rd year spanning Sheffield from Belmont to Roscoe featuring food, drinks, and live music by local street fest favorites like To the 9’s and Too White Crew.

Randolph Street Market Festival

memorial day weekend chicago

Photo Credit: Randolph Street Market Festival

1340 West Washington Street

From May 27 – 28, shop from over 300 vendors at this European-style indoor and outdoor market, including live music and entertainment. General admission is $8, kids 12 and under are free, and pets are welcome.

Memorial Day Weekend Cruise

memorial day weekend chicago

Photo Credit: Spirit Cruises

What better way to watch Memorial Day weekend fireworks than aboard a cruise ship with spectacular views of the skyline? From May 26 – 29, treat yourself to a two to three-hour cruise featuring a new buffet menu, cash bar, and live DJ entertainment.


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