Whether you're betting on an underdog like Majesto or a derby favorite like Nyquist (those are names of horses, right?) you might as well do it with a drink in your hand. While the horses and jockeys are running for the roses, we know you'll be running for the bar, which is why we've picked the best Kentucky Derby celebrations in Chicago.
Allium Restaurant and Bar: If you’re feeling fancy, head to the Allium at the Four Seasons Hotel and receive a complimentary glass of prosecco during this derby watch party. Stay for the Market Fruit Julep, made with strawberry rhubarb, and the crab hot brown brioche sandwich, topped with crispy prosciutto and pickled tomato. (Four Seasons Hotel, 120 E Delaware Pl, 6:30am–1am.)
Derby Chicago: No derby party is complete without a premium buffet and official bugler to announce the start of the race. Get your photo taken in elegant derby attire and receive a free drink from Bulleit. Don’t forget to enter the raffle—you could win four-day passes to Lollapalooza or tickets to the Time Out Chicago Bar Awards or Time Out Chicago Donut Party. (Derby Chicago, 1224 W Webster Ave, 1–5pm. $25–$275.)
El Tapeo: More than 120,000 mint juleps are served over Kentucky Derby weekend, and El Tapeo is set to serve its own twist on the Southern cocktail. Sip on a sweet Apricot Mint Julep or try out the Garden Julep made with Whistle Pig Rye, honey and a frozen ice sphere infused with simple syrup, mint and basil. (El Tapeo, 2100 Spring Road, Oak Brook, 5–11pm)
Flagship: Come dressed in an oversized hat or seersucker suit and maybe you’ll win best-dressed derby-goer. Throw back $6 Fireball shots, $6 mint juleps and $7 Buffalo Trace Old Fashioneds while you watch the fastest two minutes in sports. (Flagship, 1622 W Belmont Ave, 11am–3am.)
Fountainhead: Town Branch and Alltech’s Lexington Brewing Company are teaming up to create Kentucky-inspired specials like the Mornay smothered hot brown sandwich. Try a refreshing Town Branch Bourbon Lemonade or Against the Grain Mint Julep Ale. (Fountainhead, 1970 W Montrose Ave, 2pm.)
The Game Room: Here you’ll be able to play foosball or shoot pool while you wait for the Kentucky Derby to kick off. But let’s face it; we know you're only going for the top-notch mint juleps crafted by the beverage wizard, Paul McGee. (Chicago Athletic Association, 12 S Michigan Ave, 11am–2am.)
Howells & Hood: When you’ve got bourbon-glazed baby back ribs and chocolate pecan pie on the menu, it’s understandable if you’re too busy to pay attention to the horses. Sip on a classic mint julep or order a craft beer off the never-ending list. (Howells & Hood, 345 N Michigan Ave, 3–7pm.)
I|O Urban Roofscape: Start the day off with brunch in a big fancy hat and make the most of the Kentucky Derby on a giant rooftop with a retractable roof. If you’ve perfected Southern style, you might even win best dressed. (Godfrey Hotel, 127 W Huron St, noon–8pm. $30 general admission, $49 includes brunch, $40 VIP expedited entry)
Public House: Guests at this Southern-themed party can watch the derby on a 30-foot video wall. Sip on $6 Woodford Reserve Mint Juleps and fill up with fried chicken sandwiches or truffle mac and cheese. (Public House, 400 N State St, 10am.)
The Southern: Dive into a full Southern buffet, including hot browns, fried chicken and mac and cheese. Celebrate the champion with specials on mint juleps and beer-and-shot combos. (The Southern, 1840 W North Ave, 4–7pm. $25 per person.)