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Memorial Day is sometimes viewed as the official segue from spring to summer. Spend the long weekend cheers-ing to America's fallen heroes on some of Chicago best outdoor spaces. We're keeping our fingers crossed that the weather cooperates!

Memorial Day Opening Weekend at Castaways on North Avenue Beach

  • Saturday, May 23 to Monday, May 25

Located on North Avenue Beach, Castaways will open to the public this Memorial Day weekend with live entertainment Saturday through Monday and will serve lunch and dinner from 11 a.m. to 9 p.m. (weather permitting). Menu items include fresh salads, wraps, sandwiches, and quesadillas accompanied by frozen cocktails and even Corona in a can (No bottles on the beach).

Castaways now offers Cabanas available for rent daily through Labor Day. The two cabanas are located on the North end of the Castaways upper deck with a capacity of 10 - 12 people (max) each. The cabanas are available for rent from 11 a.m. - 7 p.m. ($1500 F&B minimum).

Saturday, May 23

1 p.m. to 7 p.m.: DJ Jem & The Dance Floor Junkies

Sunday, May 24

1 p.m. to 7 p.m.: DJ Jem & The Dance Floor Junkies

Monday, May 25

1 p.m. to 7 p.m.: Sunfallen

Frontier Memorial Day Crawfish Boil

  • Sunday, May 24 at 3 p.m.
  • $25 per person (tax and gratuity not included)

Frontier (1072 N. Milwaukee) invites Chicagoans to an authentic Louisiana crawfish boil with the Who Dat Nation Chicago Chapter on Sunday, May 24 beginning at 3 p.m. For $25 per person, guests will enjoy an all-you-can-eat crawfish boil complete with potatoes and corn-on-the-cob prepared exclusively by Pioneer Tavern Group Corporate Chef Brian Jupiter. Purchase tickets at

Kanela Memorial Day Al Fresco Dining

  • Friday, May 22 to Monday, May 25

Guests who dine at Kanela Lakeview, Old Town or Wicker Park over Memorial Day weekend will enjoy their al fresco dining all weekend long. The charming enclosed patio at the Lakeview location seats up to 40 guests, and full food and drink menus are available for al fresco dining. The Old Town location offers intimate al fresco dining, weather permitting. The flower-lined sidewalk patio features seating for 14 guests, and full food and drink menus are available. And debuting this year, Kanela Wicker Park features an intimate sidewalk patio on Milwaukee Avenue features seating for 14 guests, and full food and drink menus are available

LandShark-Beer-Garden-REVAMPED 3
Jam out to live music at weekend at LandShark Beer Garden on Navy Pier.

Memorial Day Outdoor Dining at the LandShark Beer Garden

  • Friday, May 22 to Monday, May 25

The LandShark Beer Garden, on the East End of Navy Pier, is a great place to unwind during Memorial Day Weekend and enjoy Chicago's lakefront while listening to the hottest local bands (Memorial Day Weekend live music schedule below). At the center of the action by day or night, The Navy Pier Beer Garden is the perfect backdrop for fun social gatherings and casual corporate events.

Friday, May 22

7 p.m. to 8 p.m.: Mike Flood & Co

9 p.m. to 11:30 p.m.: Back Country Roads

Saturday, May 23

2 p.m. - 4:30 p.m.: Bassel & The Supernaturals

5:30 p.m. to 8 p.m.: The Congregation

9 p.m. to 11:30 p.m.: Mike & Joe

Sunday, May 24

2 p.m. to 4:30 p.m.: Safe Haven

5:30 p.m. to 8 p.m.: Nicholas Barron

9 p.m. to 11:30 p.m.: Samadhi Vibe

Monday, May 25

5:30 p.m. to 8 p.m.:Train Company

Lottie's Annual Memorial Day Pig Roast

  • Sunday, May 24 at 2 p.m.
  • $12 per person

Lottie's Pub (1925 W. Cortland) in Bucktown will host its 5th Annual Memorial Weekend Pig Roast on Sunday, May 25 beginning at 2 p.m. For $12 per person, guests will enjoy an all-you-can-eat cured and smoked pig roast from Frontier, complete with baked beans, potato salad and coleslaw. Guests can wash it down with $15 Miller and Coors buckets, $4 Sam Adams Seasonal pints, and $4 Absolut Lemonades served in mason jars.

MAK Memorial Day Al Fresco Dining

  • Friday, May 22 to Monday, May 25

Perfect for outdoor Memorial Day dining, MAK (1924 W. Division) offers casual al fresco dining, weather permitting. The patio features seating for 28 guests and full menus are available. MAK offers the dynamic flavors of traditional Chinese cuisine with a healthy and modern twist featuring flavorful food based on recipes handed down from generations.

Mondo-Meatball Patio-1
Mondo Meatball's patio is one of the newest outdoor dining additions to Wicker Park.

$3 Beers for Three Days for Memorial Day Weekend at Mondo Meatball

  • Saturday, May 23 to Monday, May 25
  • $3 Peroni and Hoegaarden

To celebrate the three day weekend, Mondo Meatball (1467 N. Milwaukee) in Wicker Park will offer $3 beers for three days, Saturday, May 23 through Monday, May 25. Mondo Meatball is typically closed on Mondays but will open for the Memorial Day holiday. $3 beers will include Peroni and Hoegaarden. Guests can also enjoy a globally-inspired, one-of-a-kind selection of meatballs and sauces as well as sides like polenta, risotto, mashed potatoes, veggies and more. With its brand new sidewalk patio that seats 14, Mondo Meatball is a perfect choice for relaxing over the long weekend.

Municipal Bar Memorial Day Specials

  • Monday, May 25

In celebration of Memorial Day, Municipal (216 W. Ohio) will feature several specials and events on Monday, May 25. Guests will enjoy 50-percent off of appetizers and $2 sliders from 4 p.m. to 6 p.m. Additionally, for the Blackhawks playoffs, Municipal will feature their Hawks specials including $15 Bud Light buckets, $5 22-ounce Bud Light drafts and $5 Fireball shots.

Municipal will also host a “Liberty for the Industry” party from 2 p.m. to 10 p.m. sponsored by Ketel One, Bulleit Bourbon, Don Julio and Captain Morgan. All industry employees receive 50-percent off their bill as well as discounts on bottle service with proof of employment.

RIVA Cafe Memorial Day Outdoor Dining

  • Friday, May 22 to Monday, May 25

This more casual version of Riva Crab House, Chicago's premiere seafood restaurant, is the perfect stop for visitors and locals alike on lively Navy Pier this Memorial Day weekend. Riva Café accommodates guests with a superb seafood menu, gourmet sandwiches, soups, and salads. The café's outdoor seating area provides a beautiful view overlooking Lake Michigan as well as access to all of Navy Pier's fun and excitement. (Patio Capacity: 150 - 175)

Memorial Day Brunch at SIP

  • Monday, May 25

Southport & Irving (SIP), located in the heart of Lakeview (4000 N. Southport), will feature their brunch menu on Monday, May 25 from 10 a.m. to 3 p.m. The brunch menu features items like the Braised Pork Ramen, Lobster Ham and Grits, Vegetable Frittata and more. Guests can also enjoy signature brunch cocktails and al fresco dining weather permitting. The patio features seating for 30 to 35 guests, and full drink and food menus are available.

Memorial Day Weekend at Tavern on Little Fort

  • Friday, May 22 through Monday, May 25

Guests are invited to celebrate Memorial Day Weekend at Tavern on Little Fort (4128 N. Lincoln Ave.) and enjoy specials available through Memorial Day on Monday including $4 Firecracker shots (Fireball and RumChata) and $4 Blue Moon drafts. New this year, Tavern on Little Fort features a spacious outdoor patio with dining for 48 and a new beer garden that will accommodate up to 68 guests. Patrons can enjoy full bar and food menus on the patio.


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