10 Ways to Enjoy Kentucky Derby Day in Chicago


On May 4th, you don’t need to take a trip to Kentucky to fully enjoy the 150th running of the iconic Derby. We selected some great ways to celebrate the occasion in Chicago.

Watch Party at Tony’s Rooftop

Grab your friends to watch the most exciting two minutes in sports while enjoying delicious food, refreshing drinks, giveaways, photo ops, and a lively atmosphere. Featuring Whistlepig Bourbon and Rye, don’t miss out on Derby Day’s signature Mint Juleps and Sazeracs, and don’t forget to wear your best derby attire for a chance to win prizes! Admission is free but RSVP are encouraged via Eventbrite.

Industry Ales

Pick the winning horse and Industry Ales will cover your entire tab!* Join us on May 4th as early as 11am to celebrate the 150th Kentucky Derby! Enjoy $10 Mint Juleps all day long. Prizes for Best Dressed, raffle sponsored by Wild Turkey, and more! Reservation required to be eligible for promotion. Secure your table at IndustryAles.com or call (312) 496-362

Vol. 39

If you can’t make it to Kentucky, head to the Kimpton Gray Hotel’s second-floor cocktail bar for a big hat moment, where you’ll be greeted with a complimentary Mint Julep upon arrival. On Saturday, May 4 from 3-7 PM, Vol. 39 will be serving all the essentials for a memorable Derby party – from handcrafted cocktails including Mint Juleps, Whiskey Smashes, French 75s and Sazerac Rye Old Fashioneds at the champagne bar and gourmet bites from Executive Chef Luis Silva to live music, a fascinator display and a vintage photo booth. Come in your finest racing fashion for a chance to win the “Best Dressed” and “Best Hat” competitions. Tickets are $55 per person and can be purchased here.

Old Town Pour House

Old Town Pour House invites guests to experience the Kentucky Derby on Saturday, May 4, with the race displayed on large HDTV screens. Old Town Pour House provides a lively atmosphere for friends and family to enjoy the Rock N’ Roll Brunch, offering a delightful culinary experience while watching the Derby unfold. Brunch-goers can start with “Jon Bun Jovi” cinnamon rolls or “Donut Stop Believin” doughnuts, and then rock on to mains like the indulgent “Sweet Child O’ Mine” French toast or the robust “The Boss” steak and eggs. 

LG’s Bar & Kitchen

With 20 flat-panel HD televisions, you won’t miss any of the fierce competition.The Derby Day cocktail specials include Triple Crown Cooler, Julep Jamboree, Run for the rose’, Derby Day Highball. LG’S will also be offering Derby hats, fun swag, and prizes for the day. Reservations are available on OpenTable here.

I|O Godfrey

I|O Godfrey‘s 10th Annual Kentucky Derby Viewing Event event will feature bourbon tasting classes every half hour from 1 p.m. to 4 p.m., allowing attendees to reserve a spot along with their tickets. A special Derby Day menu, a photo booth, and a live mint wall will enhance the festive atmosphere. Attendees are encouraged to dress in their finest Derby attire, with prizes awarded for the best dressed, best hat, and best couple. Tickets for our exclusive event offer a range of options to suit every preference. Tickets range from $40 per person for general admission to $2,500 for Premium Large Booth for 20 guests and can be purchased here.  

Bodega Taqueria y Tequila 

This Kentucky Derby Watch Party will feature multiple TVs and a projector for race viewing, alongside food and drink specials. Post-race entertainment includes DJ sets. General admission ($10 per person) includes entry, one White Claw Hard Seltzer, socializing, and fun. Table reservations range from $96 for 8 tickets and $240 for 20 tickets. Individual and table tickets reservations can be made here

Black Barrel Lounge

Join Terry and his team at Black Barrel Lounge in Old Town for an unforgettable Kentucky Derby event. Early Bird Tickets only $10, including a complimentary Mint Julep or Champagne. Get ready for the 150th running of the roses with our DJ spinning tunes. Prizes for Best Dressed & Best Hat.

Shaw’s Oyster Bar

Partnering with Woodford Reserve, Shaw’s Chicago Oyster Bar will be serving up Kentucky Derby specials: Mint Juleps, Old Fashioneds, Spires, and Pimento Cheese Dip. For the first time, Shaw’s Crab House will feature 20 oyster varieties, each matched to a competing horse. Bet on your favorite; if it wins, enjoy a round of oysters on the house.


Dress to impress and bring your appetite to Yardbird’s Derby Day Extravaganza. Located in River North, Yardbird offers elevated Southern classics and is hosting a party with costume contests, live jazz, and more. Tickets are $65, including appetizers and three cocktails like Mint Juleps and Yardbird’s signature Old Fashioned. Menu highlights include Deviled Eggs, Kentucky BBQ Sliders, and Green Tomato & Pimento Cheese Saltines. Prizes for Best Hat, Best Couple, and Best Dressed. After the race, enjoy a post-derby Winner Circle Dinner featuring champagne and caviar.

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