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The Best Chicago Events Calendar

Chicago Events – Cinco De Mayo and Kentucky Derby Parties


Chicago Events - Cinco De Mayo and Kentucky Derby Parties

Chicago Events – Cinco De Mayo and Kentucky Derby Parties

The first weekend in May is cause for lots of celebrations….. warmer weather is nearing, bets are being placed on the Kentucky Derby, and margaritas are being tossed back at Cinco de Mayo fiestas. We’ve rounded up some of the best Chicago events for Cinco de Mayo and the Kentucky Derby including one event that combines both for a Cinco de Derby extravaganza!

Cinco de Mayo:

SafeHouse Chicago, the top hangout for Windy City’s elite spies, located at 60 E. Ontario, will be offering Cinco de Mayo specials all day on Friday, May 5. The featured items are Street Tacos ($5 each), Corona bottles ($5 each) and aNachos Combo ($20), which includes the famous SafeHouse Camp Stanley Nachos and four Coronas.

ROOF on theWit will host their Cinco De Mayo party with featured menu items including Al Pastor Tacos ($7) with cilantro and onion, Huitlacoche and Green Garlic Tacos ($7) with cilantro and onions, Pork Milanesa Torta ($8) with salsa borracha and chayote slaw, Ramp and Chihuahua Cheese Tamales ($4) with chipotle salsa, Chips and Salsa ($6) and Crab and Avocado Tostada ($7) with ginger tomato dressing and crab. Drink specials highlighted include Patron Silver Shot ($8), Patron Flight Silver, Anejo, and Reposado ($15), The Perfect Patron Margarita made with Patron Silver ($10), Spicy Passion Fruit Margarita made with Patron Reposado ($10), and ROOF Paloma made with Patron Silver ($10).

Cinco de Mayo Party at SideBar Grille Friday, May 5

Nothing says Cinco de Mayo like refreshing Margaritas! On Friday, May 5, Sidebar Grille (221 N. LaSalle) will host a celebratory Cinco de Mayo fiesta complete with drink specials (including $3 Corona and Corona Light and $7 Margaritas) and delicious bites (hello: $2 tacos!). Doors open at 11 a.m.

Kentucky Derby:

On Saturday, May 6 at 2 p.m., Chicagoans will be off to the races at ROOF on theWit ‘s Kentucky Derby Day Party & Best Dressed Runway Contest. All guests present are welcome to enter the Best Dressed Runway Contest. The Grand Prize winner will receive an all-expenses-paid getaway weekend for two to the Maker’s Mark Distillery in Loretto, Kentucky and the Runner Up will go home with a private cabana at the ROOF Memorial Day JetSet Kickoff Celebration. While enjoying the races and runway contest, guests are invited to sip on classic Mint Juleps, as well as specialty Maker’s Mark cocktails.

Across the street, Staytion Market & Bar, inside of the Renaissance Chicago Downtown Hotel, 1 W. Wacker Drive, will be hosting their “Cheers to the Derby” event from 3-6 p.m.  Staytion’s mixologists will be serving up their own local take on some Derby classics like Chicago’s Koval Bourbon Mint Juleps.

Can’t make it to Churchill Downs for the Kentucky Derby? Celebrate in Chicago instead at the St. Jude Young Professionals of Chicago’s fifth annual Day at the Derby.

Partygoers of Chicago will wear their best Kentucky Derby attire and statement hats for this annual fundraiser at Barn & Co. in Lincoln Park on May 6 from 3-6 p.m. Tickets, priced at $60, include appetizers, cocktails and traditional mint juleps. Bourbon lovers are invited to kick off the event with a VIP flight tasting from 2-3 p.m.– bumping the ticket price up to $75. In addition to a live stream of the race, we’ll host raffles, derby-themed games with prizes, a hat contest! Tickets can be purchased here.

About St. Jude Young Professionals of Chicago

Over the past 15 years, the St. Jude Young Professionals Board of Chicago has raised more than $900,000 to support St. Jude patients and their families. Our mission: Supporting St. Jude Children’s Research Hospital by uniting Chicago’s leaders of tomorrow in an effort to advance cures for pediatric cancer so that no child dies in the dawn of life.

Schoolyard Tavern & Grill Big Hat Party – Saturday, May 6
For the ultimate Kentucky Derby Day party, look no further than Schoolyard Tavern & Grill (3258 N. Southport). On Saturday, May 6, the Southport staple will saddle up for a one-of-a-kind celebration inspired by the legendary race day with drink specials and giveaways. Punters must don their best to be eligible for the best dressed (and hat!) contest. Party begins at 3 p.m.

Kentucky Derby Pizza Party at Ranalli’s – Saturday, May 6

Did anyone say all-you-can-eat PIZZA!? On Saturday, May 6, Ranalli’s (1925 N. Lincoln) will present a dashing, fun party in honor of Derby Day. For $15, guests can “party on” to tunes courtesy of the guest DJ while enjoying unlimited pizza. Drink specials include: $6 stadium cups (choice of Miller Lite, Coors Light and Leinenkugel’s Summer Shandy) and $4 Fireball shots. Party runs from 2 p.m. to 5 p.m.; tickets available, here.

Derby Day Party at Gaslight – Saturday, May 6

Gaslight (2450 N. Clark) – the Lincoln Park favorite – is bringing together a bevy of specials to celebrate Derby Day in style. A $20 ticket includes: draft beer throughout the night; one drink ticket (featured drinks include refreshing Mint Julep popsicles and Pink Lily cocktails); and scrumptious bites, including mini mac and cheese, mini hot fried chicken, deviled eggs with bacon and southern-style pecan squares. Party runs from 2 p.m. to 5 p.m.; tickets available, here.

Kentucky Derby Watch Party at Kirkwood – Saturday, May 6

Kirkwood’s (2934 N Sheffield) expansive outdoor beer garden sets the scene for a fun-filled Kentucky Derby Watch Party. Revelers can recreate the iconic horse race at the lively Lakeview hotspot with Jim Beam Mint Juleps ($8) and a best dressed competition. Party starts at 11 a.m.

Cinco de Derby:

Cinco de Derby Party at Benchmark – Saturday, May 6

Can’t decide between tequila or bourbon? Why not do both?! Benchmark (1510 N. Wells) is hosting the ultimate Derby fiesta, where guests can enjoy drinks and bites while watching the legendary two-minute race. The event will include a Bourbon 101 Tasting, Woodford Mint Julep offering (complete with copper mug), photo booth, race raffle prizes, a live Bugle player, and a best dressed and hat contest. A portion of the proceeds will be donated to Misericordia. Party begins at 2 p.m.