The Last Fling Summer Festivals around the Chicagoland Area

Tobias Roberts, August 28, 2018

The end of those long, summer evenings that are perfect for barbecue parties are in sight, and the coolness in the night air foretells the imminence of our notorious Chicago winters. Sadly, summer is coming to an end, but Chicagoans won´t let it go without a bang. Labor Day is the perfect excuse to keep the spirit of summer alive, and there are several, rocking summer fling festivals across the city that will help you to squeeze out the last ounce of summer fun before cooler weather sets in. Below, we look at the best late summer festivals that you simply cannot miss.

40th Annual Chicago Jazz Festival

  • Date: August 29th to September 2nd
  • Time: 11:00 am – 9:00 pm
  • Location: Chicago Cultural Center, Millennium Park and other venues across Chicago

Chicago has quite a varied music scene, but nothing is more distinctive than the “Chicago style” of jazz that originated when southern musicians moved to the city in the 1920s. The “hot jazz” of Chicago was originally characterized by King Oliver and Jelly Roll Morton and has made Chicago one of the leading jazz scenes across the country.

The 40th annual Chicago Jazz Festival will be held from August 29th to September 2nd this year at both Millennium Park and the Chicago Cultural Center and showcases dozens of free live performances by both Chicago jazz musicians and some of the most renowned jazz musicians from around the world on multiple stages.

If you are a jazz enthusiast, you won´t want to miss a live performance by the 83-year-old Ramsey Lewis on September 1st at the Jay Pritzker Pavilion as this will be his last show in Chicago before retiring. Maceo Parker and his super charged funk style of jazz will also be at the Jay Pritzker Pavilion on the 2nd. You can find the full line up of featured performers here.

North Coast Music Festival

  • Date: August 30th to September 3rd
  • Time:
    • Friday, August 31st, 2018: 3:00 PM – 10:00 PM
    • Saturday, September 1st, 2018: 1:00 PM – 10:00 PM
    • Sunday, September 2nd, 2018: 1:00 PM – 10:00 PM
  • Location: Union Park, 1501 W Randolph St.

The North Coast Music Festival offers a diversity of live music performances, including folk, rock, hip hop, DJ’s and other performing artists. This will be the 9th year that the festival has enlivened Labor Day weekend in Chicago.

This year´s artist lineup is headlined by the British funk-fusion act Jamiroquai, along with R&B performer, Miguel, and the electro-pop producer Mura Masa. Four curated stages will allow you to see summer off through an explosion of dance music, hip-hop and rock-bands. Over 20 local vendors offering vegetarian, vegan and non-gluten food and drink options will also be on hand.

Tickets start at $60 for a Friday pass or $164 for a 3-day pass. Children under the age of 10 can attend free of charge if accompanied by a legal guardian. You can purchase your tickets for the North Coast Music Fest here.

Festival de la Villita:  A Celebration of our Southern Neighbors

  • Date: Friday, September 07 – Sunday, September 09
  • Time: Friday: 5pm to 10pm; Saturday & Sunday: 2pm to 11pm
  • Location: 26th Street and Kostner Avenue

Just because the 4th of July is over doesn’t mean we can’t continue to celebrate Independence Day! The Festival de la Villita is the largest annual celebration of Mexican culture in the Midwest and it coincides with the “Fiestas Patrias” that celebrates Mexico´s independence from Spain in 1810. With well over half a million people in Chicago claiming Mexican origin, this second Independence Day celebration is a great way to bring summer to a fitting close.

In its 29th year, the Festival de la Villita offers a wide variety of entertainment, games, carnival rides, and well over 100 vendors of both artwork, crafts, and of course authentic Mexican food and drink. If you want a taste of Mexican pop culture, celebrities from Mexico´s infamous soap operas and sports teams also tend to make an appearance.

The best time to visit the Festival is on Sunday afternoon as the 26th Street Mexican Independence Day Parade ends at the site of the Festival and you can enjoy an amazing display of colors, dance, and music.

Throwback Music Fest in Gladstone Park

  • Date: Friday, September 07 – Sunday, September 09
  • Time:
    • Sep 7th: 4:00pm-10:30pm
    • Sep 8th: 11:00am-10:30pm
    • Sep 9th: 11:00am-10:00pm
  • Location: Gladstone Park Neighborhood. Milwaukee Avenue between Elston and Peterson Avenues

The Throwback Music Fest is billed as an opportunity to experience music time travel and enjoy the best Chicago and national bands playing throwback hits from the 50s, 60s, 70s, 80s, and 90s. The wide variety of music makes it a truly intergenerational celebration. From a Guns n Roses tribute by the local band “Night Train” to the “Flat Cats” swinging jazz and blues music and everything in between, there is surely a concert for everyone in the family. You can find the complete line up of bands set to perform at the Throwback Music Fest here.

This festival offers much more than music as there will also be kids’ activities including an arts and crafts zone, a classic car show on Sunday, and a tribute to commemorate the 17th anniversary of the September 11th attacks. Five dollar donations per person are accepted at the entrance gates and go towards a local Scholarship Fund. Free street parking on Elston and Milwaukee avenues is also available.

Windy City Wine Festival

  • Date: Friday, September 07 and Saturday, September 08
  • Time:
    • Friday: 5:00—10:00 pm
    • Saturday: 3:00—8:00 pm
  • Location: Buckingham Fountain in Grant Park, 301 S Columbus Dr, Chicago, IL 60605

If your idea of a great summer evening includes wine, great music, wine, delicious food, wine, cooking demonstrations, and of course more wine, then the Windy City Wine Festival should definitely be on your radar.

The relaxed festival ambience at the beautiful Buckingham Fountain will allow you to sample over 300 wines from around the world. You can savor locally fermented wines grown by Illinois wineries and compare to them to the best wines from Italy, Chile, France, and hundreds of other locations. This annual sommelier festival will also feature award winning restaurants and caterers who will be serving delicious meals. The live music lineup includes Grupo Paz and Tommi Zender & Co. on Friday night and The Winchesters on Saturday evening. The nightly light show illuminating the fountain will also add to an evening you won´t soon forget.

Tickets start at $45 for advance purchase or $50 at the gate and include up to 20 free wine tastings (one ounce pours). The Windy City Wine Festival also offers discounted designated driver admission for only $15 and free admission for people under 21 who are accompanied by an adult. You can pre purchase tickets here.

While you can´t bring in your own drinks to most of these festivals, preparing your own big batch of cocktails and spending a relaxing afternoon at the beach is also a prodigious way to enjoy the last days of summer.