Top Chicago Events – Summer 2019

Top Chicago Events – Summer 2019

By Anne McCarthy

Ah, Chicago summers. There’s nothing quite like them.

Summers in Chicago are a magical thing – hot nights with cold brews, new festivals every weekend, concerts galore, and more food than you can shake a stick at. If you’re fortunate enough to experience part of a Chicago summer, then count your lucky Cubs stars.

Here’s what’s going down in the Windy City this summer.


Chicago is known for – among many things (i.e. Oprah, the Bulls, etc.) – blues and jazz music. (Perhaps you’ve heard of a little Chicago-based movie called “The Blues Brothers”?)

Chicago Blues Festival (June 7 – June 9) is one of the finest blues celebrations in the country, and now, in its 36th year, this year it promises even more bluesy beats reverberating through Millennium Park.

Cost: FREE
📍 Location: Millennium Park

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Ribfest (June 14 – June 16) is Chicago’s best rib game in town. And there’s no better time or place to have your rib fill than at Ribfest in June (get your tickets here). And if you’re missing the fest, check out Twin Anchors in Old Town for some of Chicago’s most mouthwatering – and long-revered – ribs.

Cost: Tickets start at $25
📍 Location: Ribfest takes place on Lincoln Avenue, from Iriving Park Road to Berteau Avenue

Grant Park Music Festival (June 12 – Aug 17) – As melodic, symphonic scores fill the park, you’ll relish in enjoying a night’s worth of classical music, while lazing on your picnic blanket. This highly popular (get there early – it fills up fast!) event is a summer-long free classical music festival. So, escape the hustle and bustle of the Chi streets, and let your ears drown in a sweet symphony of sounds.

Cost: FREE
📍 Location: Jay Pritzker Pavilion in Millennium Park

Craft Brews at Lincoln Park Zoo (June 14 – 16) lets you step inside the zoo after-hours, and sample over 150 craft beers, all while perusing the zoo’s stunning gardens at dusk and into the summer night. Food (for purchase), DJ music, games, and animal viewings are all included with your ticket. This event sells out early, so book soon!

Cost: Tickets start at $49
📍 Location: Lincoln Park Zoo

Want to nibble on tacos and sip a margarita for a good cause? Chicago Taco & Tequila Fest (June 15) is the ideal summer fun-meets-good-deed event; the beneficiary of this fest is the Chicago Canine Rescue organization.

Cost: Tickets start at $10
📍 Location: Cannon Drive just north of Fullerton

Okay, here we GO. Chicago Pride Festival (June 22 – June 23) is one of the largest pride celebrations in the country, and certainly one of the most lively, colorful, and celebratory. So throw on your most colorful garb (ideally something rainbow-related), a splash of glitter, and an upbeat attitude. It’s hard not to enjoy yourself at this iconic event, which annually welcomes over 100,000 people.

Cost: $10 Suggested Donation
📍 Location: Boystown on Halsted Street from Addison to Grace Street

Pride Fest is the lead up to Chicago’s Pride Parade in Boystown (June 30). Check it out for an unforgettable day of, well, nothing short of amazing. You will leave the parade with high spirits, and maybe a sticker or two on your cheek.

Cost: FREE
📍 Location: Starts at Broadway & Montrose


Ring in our nation’s holiday with the 4th of July Fireworks at Navy Pier (July 4)! Watch with awe as the night sky lights up with colors across the spectrum, as the colorful lights slowly fall onto majestic Lake Michigan. Fireworks are expected to kick off around 9:30pm. (It is recommended that you arrive well before then, in order to make sure you gain entry.)

Cost: FREE
📍 Location: Navy Pier

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Taste of Chicago (July 10 – 14) – wear your stretchy pants for this one, guys. Taste of Chicago, or simply “the Taste” (as Chicagoans call it), is the world’s largest food festival. And it’s not just about the food, either. With multiple, ongoing music acts – including India.Arie this year! – you won’t be at a loss for where to look or listen while you’re noshing on some food of your choosing. This event is crowded, but worthwhile. Your stomach will thank you for your attendance.

Cost: FREE
📍 Location: Grant Park

Chicago is a proud and longtime home to many Irish men and women. The Irish American Heritage Festival (July 12 – 14) honors the local Irish of present and past. At this festival, you’ll find Irish eats, music (of course), Irish dancing (double of course), and a wealth of information about the Irish experience in Chicago and beyond.

The music acts are one of the most popular parts of the fest, and this year’s lineup includes: Dustbowl Revival, House of Hamill, Rory Makem, The Prodigals, and artists direct from the motherland: The Byrne Brothers, Shane Hennessy, McPeake, Tupelo and Derek Warfield and the Young Wolfe Tones.

Cost: Tickets start at $10
📍 Location: Irish American Heritage Center (4626 N. Knox Avenue)

Speaking of music…Pitchfork Music Festival (July 19 – July 21) is on deck yet again in the Windy City. This music aficionado event boasts the biggest and brightest alternative, indie, rock, and pop music acts. This year’s full line-up includes the likes of Robyn, HAIM, the Isley Brothers, and many more.

Cost: Single Day Tickets start $85 (June 1 – July 16, after which ticket prices rise)
📍 Location: Union Park


And in August? That’s right, more music! (And food, and some boats, and some of that famous Chicago comedy).

Lollapalooza (Aug 1 –Aug 4) – Of course, what would a Chicago summer be without “Lolla?” This Grant Park-based music fest is a popular one (even native Chicagoan, Malia Obama, was an attendee). This year’s lineup includes headliners like reigning pop Queen Ariana Grande, the keeps-you-on-your-toes sounds from Childish Gambino, and longtime favorite, the Strokes.

Cost: Tickets start at $130
📍 Location: Grant Park

The Chicago Air and Water Show (August 17 – 18) is a beloved tradition that many Chicagoans grow up attending. Free, accessible, and visually stunning, this event (which began in 1959) spans the Lake Michigan lakefront, as the sky fills up with some thrilling, gravity-defying airplane stunts (that might leave you feeling nauseous at the thought of performing them yourself).

Cost: FREE
📍 Location: The Lakefront and North Avenue Beach

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Chicago Women’s Funny Festival (August 22 – 25) – This funny fest, held annually at Stage 773 theater, is the best event to get your fill of some amazing female comedians. Chicago is known for its comedy theaters (i.e. the Second City, Improv Olympic, the Annoyance, and more); nestle yourself into a seat in this theater, Stage 773, as women who perform at various venues around Chicago converge at 773 for days of original, empowering, and, of course, hilarious material.

Cost: 2019 Ticket prices and lineup forthcoming (stay tuned here).
📍 Location: Stage 773 (1225 W. Belmont Avenue)

Chicago’s renowned Greektown is home to incredible food and culture. Taste of Greektown (August 23 – 25) offers a variety of Mediterranean delights as far as the eye can see at this West Loop event, which is now in its 30th year.

Cost: $5 Suggested Donation
📍 Location: 400 S. Halsted Street

Along the shores of Lake Michigan, the Chicago Triathlon (August 24 – 25) athletes will be embarking on a battle of the wills, summoning energy to conquer the bike course, the choppy waters, and the running course.

Cost: Free to spectate
📍 Location: Chicago Lakefront

This triathlon is a thrilling spectator event, and perhaps you’ll even feel inspired to tackle a physical activity of your own. If so, check out a Chicago Day Bike Tour with Fat Tire Tours. (Most assuredly, your bike tour will not require an intensive training beforehand, unlike the triathletes.)

Cost: $39
📍 Location: 910 S. Michigan Avenue #130

[maxbutton id=”1″ url=”https://www.fattiretours.com/blog/chicago/fat-tire-tours-best-of-chicago” text=”Don’t miss our Best of Chicago list!” ]

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