By Jacqueline Runice

Labor Day – a bittersweet holiday for parents, summer lovers and tourism officials. If the scent of just-sharpened pencils or the prospect of checking out the new freshmen class isn’t on September’s calendar any longer, lighten up with some of these singular Chicago events that will help you kiss summer 2017 “au revoir” with a smile on your face.

Chicago Jazz Festival
Millennium Park
201 E. Randolph St.
Chicago, IL 60602
(312) 744-3316

Date: Thursday, Aug. 31 through Sunday, Sept. 3, 2017 at 11 a.m.

A Labor Day weekend tradition that’s as exciting as the American art form itself, the 39th Chicago Jazz Festival opens with performances by the Dave Rempis Quintet, the Chicago Jazz Composers Collective and Jon Faddis and continues throughout the weekend with headliners like the Dr. Lonnie Smith Trio, Allison Miller Boom Tic Boom. and the Rebirth Brass Band. Don’t miss pianist and MacArthur Fellow, Jason Moran leading a special centennial celebration performance for Thelonius Monk with a presentation of In My Mind: Monk at Town Hall 1959. One of the most comprehensive free jazz festivals in the world, the fest offers general seating in the Pavilion and on the Great Lawn on a first-come, first-served basis. Feel free to tote a picnic basket and dine al fresco listening to a great American musical innovation.

Castaways Bar & Grill
1603 N. Lake Shore Drive
North Avenue Beach
Chicago, IL 60614
(773) 281-1200

Date: Saturday, Sept. 2 through Monday, Sept. 4, 2017 at 11 a.m. until 11 p.m.

Labor Day and the beach go together like Kim and Kanye – full of selfie opps and a love story straight of out Central Casting. Castaways Bar & Grill’s Labor Day Weekend End-Of-Season Party is directly on North Ave. Beach and will feature live entertainment by DJ Jem from 1 p.m. to 7 p.m. on Saturday, Sept. 2 (KISS FM live broadcast from 2 to 6 p.m.), Sunday, Sept. 3, and Monday, Sept. 4. Watch the moves of your favorite lifeguard while sipping on the last frozen cocktails of the season like fruity pina and strawberry coladas, and mango Margaritas. Lunch and dinner will be served from 11 a.m. to 9 p.m. (weather permitting), with menu items like fresh salads, wraps, sandwiches and quesadillas.

North Coast Music Festival
Union Park
1501 W. Randolph St.
Chicago, IL, 60607
(323) 908-0607

Date: Friday, Sept. 1. 2017 at 3 p.m.

The all-ages home grown music festival takes over Union Park all weekend (Sept. 1-3) presenting established and emerging artists chosen by independent promoters in Chicago. The line-up includes Gucci Mane; STS9; Ween; Carnage; Primus; Big Boi; Tipper; tons of DJs and after parties at clubs like The Mid, Concord Music Hall and Prysm Nightclub. Expect a Pop-Up Gallery and various installations around the park, free yoga sessions to work out the kinks and a Living Gallery of graffiti and street art in which you can listen to a special curated channel on your headphones while watching artists create in the moment.

Related: Neighborhood Guide: River North

Jetset Series
ROOF ON theWit
201 N. State Street – 27th Floor
Chicago, IL 60601
(312) 239-9502

Date: Friday, Sept. 1 through Saturday, Sept. 2. 2017 at 2 p.m.

The boutique hotel brought back its summer series that recreates global party destinations on its popular rooftop venue accented by great food, drinks and sultry evening breezes. The final destination is Lisbon, Portugal over Labor Day weekend when the rhythm of Portuguese music, scents and tastes of exotic bites and cold unique drinks await revelers to say “Tchau” to summer.  ROOF on theWit’s exclusive sensual immersion, complete with Chef Nathan Sears’ take on Portuguese food, plus panoramic skyline views, is a singular send-off to summer.

Navy Pier
700 E. Grand
Chicago, IL 60611
(312) 595-5446

Date: Friday, Sept. 1 though Sunday, Sept. 4 at 11 a.m.

Of course it’s crawling with tourists but the prospect of sitting on the pier, watching sailboats in the sun with dazzling views of the stellar skyline?  Priceless. And pretty perfect if you take advantage of live music and half-price Margaritas at the Miller Lite Beer Garden on the lakefront at the east end of the Pier.

It begins with Happy Hour on Friday, Sept. 1 from 4 to 6 p.m. featuring beer, cocktail and food specials. The “Live on the Lake!” music series presents local bands all weekend long and on Saturday, Sept. 2, you can be thrilled with the fireworks on Navy Pier at 10:15 p.m. The beer garden will feature half-priced margaritas for $5.50 each (available all day Labor Day) to pair with live music, beer-soaked brats, burgers, hand-tossed pizza and more. You can also soak in summer sun and views of Navy Pier, Lake Michigan and the city skyline on Chango Loco’s patio located next to Navy Pier’s Crystal Gardens. On Monday, Sept. 4, the seasonal outdoor area will offer a special Labor Day Happy Hour featuring half-price margaritas from 4 to 8 p.m. for $5.50 each.

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