Kentucky Derby 2018 in Chicago: Where to watch, bet and sip mint juleps

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You don’t have to trek to Louisville to toast the derby with mint juleps May 5. | Sun-Times file photo

The “Greatest Two Minutes in Sports” returns to the Churchill Downs racetrack in Louisville Saturday, but most Chicagoans will skip the nearly five-hour drive (or $200-plus flight) to our southeast neighbor-state to watch the 144th Kentucky Derby live. That doesn’t mean we can’t dust off an elaborate hat or bow tie and sip mint juleps to mark the occasion. Venues across the city will stream the race May 5 at shindigs that will long outlast the action. Whether you’re looking for a true reenactment, or just an excuse to go ham on some top-notch barbecue, our roundup of local derby day shindigs has options for everyone.

For a Churchill Downs dupe

If you can’t make it to Louisville for the main event, but still want the racetrack experience, Arlington Park is the closest (to Chicago) that you can get. While all-inclusive packages and lower-level tables are sold out, general admission passes are still available (for $18 in advance; skip the surcharge at the door) as are box seats for $22-32. If you make a mean mint julep yourself, BYO and pay just a $5-8 cooler carry-in fee. Arlington Park, 2200 W. Euclid Ave., Arlington Heights. Tickets $18-32.

If you dress to impress

Derby day attire calls for crisp bow ties and flamboyant hats—at minimum. If you plan to showcase some next-level style, strut your stuff to Luxbar near Rush and Division to compete in their best dressed contest. Prizes include a $250 gift card to Charles Ifergan salon for the winning woman and a $250 gift card to Luxbar for the best-dressed man. Win or lose, guests can enjoy a special menu of derby day drinks and snacks all day, and watch a live stream of the race around 5:30 p.m. Luxbar, 18 E. Bellevue Pl. Free.

If thoroughbreds aren’t your thing

There’s fun to be had on Saturday even if you’re blasé about the big event. The Pony Inn in Lakeview will be hosting live music from 3-6 p.m alongside Woodford Reserve mint juleps, craft cocktails and an all-you-can-eat Southern-style buffet that features a bourbon-smoked pig, fried chicken, coleslaw, corn bread and more. Tickets include buffet, mint juleps, beer, wine and Pony punch. The Pony Inn, 1638 W. Belmont Ave. Tickets $50.

For double the holiday fun

Cinco de Mayo and the Kentucky Derby both land Saturday, May 5 this year, and Mac’s Wood Grilled in West Town aims to celebrate both. Their all-day “Cinco de Derby” specials include $3 Tecate cans, $10 W.L. Weller Special Reserve Mint Juleps, $12 Peloton de la Muerte Mezcal Palomas and $3 ground beef tacos. Pre-race coverage will be screened before the 5:34 p.m. post time, and the party will continue until close at 3 a.m. Mac’s Wood Grilled, 1801 W. Division St. Free.

To eat like a horse

Fried food and barbecue often overshadow restaurants’ “Southern-style” derby menus, but Brownstone in North Center does things differently at its annual day-long crawfish boil. From 11 a.m. “til it’s gone!” they’ll serve all-you-can-eat crawfish with sides. Seating is first-come, first-served. Save $5 by ordering tickets in advance online, available until midnight tonight. Brownstone Tavern & Grill, 3937 N. Lincoln Ave. Tickets $30/$35 at the door.

For a full day of fun

If you plan to half-watch the race, but commit fully to the cocktail menu, the five-stop Derby De Mayo River North Club Crawl is for you. The $20 wristband unlocks derby- and Cinco de Mayo-themed specials (mint juleps, margaritas and more) at Bottled Blonde, Studio Paris, Old Crow, Joy District and Concrete Cowboy from noon to 11 p.m. Bottled Blonde will also host a “pre-party” and wristband pickup Friday night from 10 p.m. to 11:30 p.m. Multiple locations, see event listing for details. Tickets $20.

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