End of Summer Events Near Oak Park

Summer in the near west suburbs brings with it a lively lineup of exciting activities. From outdoor concerts and homecoming events to a vibrant art walk and community celebrations, there's always something fun happening just due west of Chicago in Oak Park and beyond. 

 

Use this guide to plan!

 


ALL SUMMER

 

Free Outdoor Summer Concerts  

 

Parks and amphitheaters in Oak Park and beyond offer free concerts all summer long. Bring a blanket, chairs, and a picnic basket to enjoy magical evenings with friends and family. 

 

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First Fridays Oak Park | Oak Park, IL | August 1, September 5, October 3, 2025

 

Oak Park’s popular First Fridays series returns with three more evenings of community, creativity, and good vibes. Each month, a different district transforms into a lively block party with live music, local food vendors, shopping pop-ups, art experiences, and fun for all ages.

 

  • August 1 | Madison Street
    Kick off the month where energy meets elegance. Madison Street lights up with live music, street eats, boutique shopping, and a festive crowd that keeps things buzzing from 5:00 to 9:00 p.m.

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  • September 5 | Southtown
    This neighborhood gem brings together indie shops, creative makers, and a relaxed block party feel. Expect laid-back vibes, local flavors, and hands-on fun.

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  • October 3 | Pleasant District
    The Pleasant District closes out the season with flair—think live jazz, family-friendly games, stylish storefronts, and cool cocktails under the stars.

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Each First Friday event offers a fresh experience, but all are packed with Oak Park charm. Whether you're bringing the family, meeting up with friends, or exploring solo, it’s a celebration of everything that makes this community shine.

 

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Uncorked | Oak Park Conservatory, Oak Park, IL | Fridays, 6:00-8:00 p.m.

 

Summertime is the best time to enjoy an evening of music, drinks, and bites in the Oak Park Conservatory’s Rubinstein Garden. Admission is $25 ($20 for Friends of the Oak Park Conservatory members) and includes two drink tickets, an appetizer, and a guided tour of the showrooms. Advance sales only; tickets will not be sold at the door. 

 

  • August 22: James Robinson-Parran

Sponsoring vendors: Empanadus and Todd & Holland Tea Merchants

Register

 

  • September 26: The Replays

Sponsoring vendors: Taco Mucho and Blackout Bakery 

Registration TBD

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AUGUST

 

Riverside 150 Homecoming Weekend | Riverside, IL | August 8-9, 2025

 

Celebrate 150 years of iconic, Olmsted-designed Riverside with a weekend of events that blend history, music, food, and local pride. Kick off the celebration with Ride Riverside Slow Roll, a 4- to 5-mile family-friendly bike ride around the picturesque community on Friday, August 8. 

 

Meet at the Riverside Train Station at 6:00 p.m. Wear your helmet and decorate your bike for this slow, social ride. 

Other events include a Friday night concert in Big Ball Park; a car show at Guthrie Park on Saturday afternoon, August 9; the Popcorn, Pizza & Pajama Party at the Quincy Community Center later that day; and the Sesquicentennial Soiree beginning at 6:30 Saturday evening at the Riverside Train Station. 

 

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Garage Galleries Forest Park | Forest Park, IL | Saturday, August 23, 2025

 

Art lovers, rejoice: Forest Park’s art walk returns this summer on August 23 with 90 artists showcasing work in 40 neighborhood garages from 11:00 a.m. to 6:00 p.m. It’s a delightful mix of fine art and funky finds, and a true celebration of local creativity.

 

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Taste of Melrose Park | Melrose Park Civic Center | August 29-31, 2025

 

This beloved food festival has been celebrating the rich culture and flavors of Melrose Park for more than 40 years. Tantalizing tastebuds with everything from Italian sausage to tamales, it’s one of the most flavorful ways to close out summer.

 

Enjoy unlimited carnival rides on Saturday and Sunday, along with a fireworks display on Sunday at 9:30 p.m. The main stage will feature continuous entertainment, including the Jesse White Tumbling Team, Chicago Garda Pipes & Drums, and tribute bands Soul Sacrifice: A Salute to Santana and Are You Ready for It? A Taylor Experience. Deja Vu and Tony Ocean & the Rat Pack are among the local favorites performing at Peroni Garden.

 

There is no admission fee for this event, and all food vendors will price their items at $5 or less.

 

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Maywood Fest & SummerJam R&B | Veterans Park, Maywood, IL | August 29-31, 2025

 

This festival, which began as a simple community picnic, has evolved into a three-day celebration of community pride featuring food and drink from more than 30 local vendors, as well as carnival rides, a teen zone, live music and comedy on two stages, and additional family-friendly activities. 

 

This year, one of the highlights of Maywood Fest includes an R&B SummerJam on Sunday, August 31, starring the Isley Brothers, Tyrese, Tank, Keke Wyatt, Lyfe Jennings, Silk, and others. Bring your lawn chairs for iconic performances, exclusive food trucks, and more festival activities for attendees of all ages. 

 

SummerJam tickets for Maywood residents will be available for pickup at Village Hall (40 Madison Street) starting Monday, July 14, from noon to 4:00 p.m. Non-Maywood residents can purchase tickets at bit.ly/RnBSummerJam.

 

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INTO SEPTEMBER

 

Art Deco Walking Tour | Oak Park, IL | September 6, 2025

 

Downtown Oak Park features a variety of stunning Art Deco architecture that is often overlooked. Join Oak Park River Forest Museum guides on a walk along Lake Street as they highlight treasures you might pass by every day without noticing. The tour begins at 10:00 a.m. in the lobby of the Medical Arts Building (715 Lake Street), heads toward Harlem Avenue, and then loops back to the starting point. Street and garage parking are available. This is a must-do for design lovers and local history buffs alike. Tickets are $10 ($8 for museum members). Purchase tickets online in advance or by calling 708-848-6755.


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Celebrate Summer in Oak Park and Beyond 

 

The freezing cold temps in winter make summers in Chicago all the more beautiful. Just west of the city, in Oak Park and beyond, celebrate summer with free concerts, sporting events, street festivals, and more goings-on that appeal to everyone.