The #gaanguide to Chicago, Illinois

Chicago, IL, illinois, the bean, mag mile, Trump

Photo by Matt Lapinski

We may be partial (Chi-town Pride!), but there is no better place to explore in the summer than Chicago, IL. The winters may be long, but Chicagoans stick it out & live for the May thru October weather. And boy, is it worth a warm weather adventure! The city comes alive during the summer and it’s the perfect time to experience the lively, culturally rich metropolis on beautiful Lake Michigan. So come along on this very special Street Fest edition of the #gaanguide to our hometown, Chicago, Illinois.

 Chicago, Illinois, chi-town

Chicago is a neighborhood city, and each neighborhood has its own vibe, community feels and during the summer months, the favorite Chicago past time of street festivals. July happens to be the peak of festival season, so whether you arrive in the beginning, middle or end of the month, you can explore different areas of the city and access all the best food, retail, music, and local artists – all in one spot! We’ve picked a few of our favorites happening across the city throughout the month of July. Get ready for the best fests in the Midwest!


First off: some logistics. In Chicago – you do not need to rent a car, and if you plan your time right, can avoid time in taxis, rideshares, and street vehicles altogether. We recommend exploring by foot, Divvy bike, water taxi, the newly released scooters, or the world-class public transit system (otherwise known as the “L”). With any combination of these easy-to-navigate options, you can quickly and affordably see the city from end to end, airport to airport and venture into the hearts of Chicago’s most iconic neighborhoods.


Second, we’re going to assume that if you’re in Chicago over July 4th, you’re well aware of the many fireworks displays that happen around town. Catch the big show from North Avenue Beach, Navy Pier, or anywhere with a clear view of the lakefront (also on display every Wednesday and Saturday night between Memorial Day and Labor Day), or skip the crowds and catch any of the hundreds of neighborhood fireworks shows put on by the city on Park District property. Our recommendation – find a rooftop and watch them all. There’s truly not a bad view of the Chicago skyline and you’ll catch a 360-degree firework spectacular from bird’s eye view. Nothing more magical in our opinion!


With the basics out of the way, ready, set, let’s FEST!

 Chicago, IL, lakefront, city, fog

Photo by Matt Lapinski

July 4th – July 7th

First up, we’ve got West Fest. This street fair celebrates West Town, an ever-evolving neighborhood pocket directly west of the Chicago River. West Fest boasts three days of live music across two stages and cuisine from some of the neighborhoods best spots. We love long-time local favorite Flo, who will be serving up their iconic breakfast burritos smothered in homemade mole sauce and imported hatch green chile salsa, and the Devil’s Food Cupcakes from West Town Bakery and a creamy, hand-scooped Goat Cheese & Blackberry cone from Black Dog Gelato. Add in local craft beers from Revolution Brewery, a dedicated kids area with a performance from Chicago’s School of Rock, and a pet parade – you’re really going to see the very best that West Town has to offer in one place.  There are plenty of stations to park or pick up a Divvy bike along Chicago Avenue where the festival is held.


If you’re looking for an alternative to West Fest, or want to go renegade and do a multi-fest weekend, here are some other options for the first weekend in July.

 street fest, festival

Windy City RibFest in Uptown has beer, wine, bands, arts & crafts, and afternoon kids’ activities in yet another up and coming neighborhood on the North Side. Oh, and did we mention Chicago-style ribs from over 25 local restaurants? Yes, please. Bring your appetite and our body cleansing & personal use wipes for a proper wipe-down after you indulge!


Anyone up for a little Reggae? The African/Caribbean International Festival of Life in Washington Park on the South Side of Chicago features African art & crafts, authentic Caribbean & African food, a soccer tournament, and 50 musical acts including legendary reggae groups to gospel choirs.

 Chicago, Trump, downtown, L

Photo by Matt Lapinski

July 12th – July 14th


It’s going to be hard to choose just one neighborhood festival for mid-July in Chicago. We’ve pooled a few of our most favorites, celebrating a wide range of cultural traditions, foods, and performances.


The Square Roots Festival is in the heart of Lincoln Square and it’s one of our favorite neighborhoods in Chicago. This diverse neighborhood is rich in history and is host to many authentic German, Swedish and Scandinavian restaurants and shops. The festival has an equally diverse music line up from local indie rockers to world stars. You can expect nightly dance parties, open jam sessions, craft beer, neighborhood food from favorites like Gather (hello Crispy Cauliflower with mango salsa, hazelnut butter, dukkah spice blend and micro cilantro), Groundswell Coffee Roasters and Chicago icon Byron’s Hot Dogs (don’t skip the cheese fries and make sure you hold the ketchup in this town!).


The infamous Windy City Smokeout is from July 12th – 14th featuring indisputably the best barbeque in the Midwest & beyond, local brews and spirits, and one hot line up of Country Western musical performances (we’re fangirling over Jessie James Decker who’s making her second debut at the annual Smokeout).


Not into country music and looking for something with a little more history? Perfect! Head over to the Irish American Heritage Festival for the finest in local and international Irish and American music, authentic Irish food & drink, community dance, and family activities. The festival is held on the grounds of the Irish American Heritage Center and doubles as a huge fundraiser for Chicago’s Irish Community Center.


Feel like exploring some of Chicago’s most beautiful homes and Gardens? The Bucktown Garden Walk & Block Party is also the weekend of July 12th. You’ll stroll through one of Chicago’s most vibrant and eclectic neighborhoods by way of over 80 exclusive private gardens and community greens spaces, offering attendees a unique way to see urban gardens, patios, and rooftops that would otherwise be hidden from public view. Take a self-guided tour or catch the free trolley to bring you from home to home. The Block Party will host a Rosé and Beer Garden, over 20 local food trucks or pop into one of Bucktown’s many hot spots like Small Cheval (one of the best burgers in the world, folks!), the original Goddess & Grocer featuring curated made-in-Chicago goods, and Jeni’s Ice Cream. Make sure you remember your all-natural mosquito repellent wipes for the Garden Walk so the only bites you’re dealing with are from that juicy burger.

flowers, garden walk


July 19th – July 21st

This weekend is also going to be an exciting one if you’re in Chicago. The fests are plentiful!


First up is the 4th annual Tacos Y Tamales Festival in the historic Pilsen neighborhood. This neighborhood is known for it’s Latin-American culture, and the festival is located along the 16th Street murals. Local, as well as National and International artists have their works displayed on nearly two miles of building and city-owned walls, making for a significant and beautiful backdrop for the event. Definitely many photo ops – so make sure you’re looking fresh with gaan + co and smile big. It’s also no surprise that Pilsen is home to some of the tastiest, most authentic Latin-influenced food in the country (hence the festival dedicated to it!). Tacos Y Tamales is going to be an experience for eating and drinking, so we highly recommend making the bike trip to Pilsen – it’s about 4 miles southwest of downtown and will get your blood pumping and stomach growling. You’ll likely hear the Latin Rock Music from a mile away, and once you park your Divvy, you can partake in a Tequila Tasting, and of course, eat all the tacos and tamales. In a culture where authenticity matters, this fest delivers on both the quality and quantity of ethnic food selection featuring over 50 restaurants and street vendors.


Pitchfork Music Festival running fourteen years strong in Union Park. This free-spirited music experience features many popular and up-and-coming names in alternative rock, rap and hip-hop, electronica, and dance music. This year, HAIM, Robyn, Charlie XCX, Belle & Sebastian, Mavis Staples and The Isley Brother’s are amongst some of the 100 performances, and you can enjoy Pitchfork’s notorious upscale festival food, as well as an arts & crafts market with local vendors.


If you want to explore another culturally rich neighborhood, head south again to the 40th annual Chinatown Summer Fair on the 21st. Don’t miss the Lion Dance Procession to kick off the event at 12:30pm followed by Asian dance performances, Martial Arts demonstrations, and samplings from Chinatown’s best restaurants. This might be the perfect opportunity to take Chicago’s famous L train, just hop on the red line to Cermak and you’ll get off the train in the center of the action!



July 26th – July 28th


We’re rounding out July with a final recommendation for the last weekend of the month. Wicker Park Music Festival will again bring you to an exciting and lively Chicago neighborhood with gorgeous architectural homes, farmer’s markets and fashionable folks. This is undoubtedly a highly anticipated summer festival and draws the crowds to prove it. The lineup of over 50 performers across four main stages reflects the neighborhood’s rich musical heritage and vibrant nightlife scene. In other words, wear your dancing shoes and be prepared to get your sweat on. Speaking of sweat, some of the areas’ best fitness experiences will be coming out to the fest on Saturday including Mirepoix Studio Yoga, Dynamic Force Dance, and MixxedFit to name a few. You’ll also get to try the food from some of Wicker Park’s most acclaimed restaurants sans the waitlist for reservations!


kobra, artist, street art, wicker park
Brazilian artist Kobra and one of his iconic street art pieces in Wicker Park


If you can’t tell, we’ve got a lot of heart for the city of Chicago and the festival culture is truly one of a kind. There are plenty of other fests happening across July that we didn’t touch on (you may have heard of the internationally recognized Taste of Chicago smack in the middle of the month), and it’s an awesome way to take in a lot of what Chicago has to offer in a short period of time. We hope you get to experience some of the finest food, music, and people in the country during the sunshine season in the Windy City! Make sure you bring along the gaan + co - the ultimate fest necessity no matter where your Chicago adventure takes you! 

Chicago, L, downtown, city


- Written by Rachel Levy