2025 Chicago Stakes Preview

Older filly and mare sprinters take the stage in the Grade 2, $300,000 Chicago Stakes at Churchill Downs on Saturday, June 21. The race drew a competitive field of 11 to go seven furlongs on the dirt, the same distance as the Breeders’ Cup Filly and Mare Sprint at Del Mar on November 1 at Del Mar.

A feature at Arlington Park since 1986, the race earned Grade 3 designation starting in 1992 after Safely Kept, winner of the Breeders’ Cup Sprint in 1990, won the race in 1991. In the ensuing years, the race was won by national stars like Informed Decision (2009, 2010), Happy Ticket (2005), and My Trusty Cat (2004), as well as local heroes like Hotshot Anna (2018), My Mertie (2019), My Option (2014), and Sarah Sis (2016).

After Arlington closed at the end of the 2021 meet, the Chicago Stakes moved to a new phase of its history: to the dirt at Churchill Downs. Top-class winners like Society (2023) and Vahva (2024) earned the race an upgrade to Grade 2 status for 2025. Vahva leads the field in her attempt to repeat, but the task will be tough in such a big field … and the rewards will be rich for handicappers who solve the puzzle.

Chicago Stakes Information

• Race Date: Saturday, June 21
• Track:Churchill Downs
• Post Time: 10:11 p.m. ET
• Distance: seven furlongs
• Age/Sex: four-year-olds and upward, fillies and mares
• Where to Watch: FanDuel TV
• Where to Bet: FanDuel Racing

Chicago Stakes Draw and Odds

This is the official field for the Chicago Stakes, including post positions, trainers, jockeys, and morning-line odds.

Chicago Stakes Prep Race Results

The 11 horses in the Chicago Stakes field come out of nine different races.

Unsurprisingly, the two races with more than one last-out runner are both sprint stakes races at Churchill Downs. Two get a class drop from the Derby City Distaff (G1) on Kentucky Derby day: Emery was fifth in that race, and Vahva was seventh. Two others come out of the Winning Colors (G3) on May 26, fourth-place Brightwork and fifth-place Mink’s Palace.

Other than that pair, the only one coming out of a graded-stakes event is My Mane Squeeze, who was third to Jody’s Pride as the favorite in the Ruffian (G2) on May 10 at Aqueduct.

The only last-out stakes winner is Zeitlos, who comes out of a 1 ½-length victory in the six-furlong Skipat at Pimlico on May 17, on the Preakness undercard. Two others come out of placings in ungraded stakes races: Gray Lightning was second, just a head behind the millionaire Oeuvre, in the Third Chance at Hawthorne on May 18. Harbor Springs has freshened since a third behind Mink’s Palace in the Roxelana at Churchill on April 26.

The other three come out of non-stakes events, and all are last-out winners. Claret Beret won a one-mile handicap on the Gulfstream dirt on May 11, Marmalade Skye won a six-furlong second-level allowance/optional claimer at Churchill Downs on May 24, and Pigalle won a third-level allowance going seven and a half furlongs on the Churchill Downs dirt on May 30.

Chicago Stakes Contenders

These are the nine contenders entered in the Chicago:

1. Emery: In a race without a ton of early speed drawn into it, the combination of Emery’s class and her early speed could be a big plus. The big question is the trip, as she’s drawn on the rail and will need a good break. But, she won the Raven Run (G2) at this distance before from the fence, and she has been in the exacta five of six times at this trip. So, if this Brad Cox trainee can survive the early pace battle with Gray Lightning, she is likely to be the one they have to catch in the lane.
2. Mink’s Palace: This Eddie Kenneally charge broke through in stakes company two back in the Roxelana, going six furlongs at Churchill Downs, though she regressed next out in the Winning Colors, her graded stakes debut. She had had runs of “good race, bad race,” meaning if she bounces back to her Roxelana form, she isn’t too far away. However, the seven furlongs is a big question: she has never hit the board going this long, meaning she needs a big step forward, not just in speed but also stamina.
3. Gray Lightning: For a horse who started her career for a $40,000 tag at Parx, she has made good. She was third in a listed race at Saratoga last year for her stakes debut, moved from the barn of Tyler Servis to that of Chicago local Armando Hernandez, and has finished in the superfecta in three straight stakes in her three tries for the new barn. Her speed is her biggest asset—for a sprint race, this race didn’t draw much in the way of frontrunners, so especially if Emery gets a rough start from the rail, Gray Lightning can try to steal this.
4. Brightwork: In terms of back class, this John Ortiz trainee is one of the leaders: she won three stakes, including the seven-furlong Spinaway (G1) at two, and also won the Prioress (G2) going six furlongs as a sophomore. She was flat in the Winning Colors last out, but that was her first race since October, so she perhaps needed it. Her juvenile form suggests extended sprint trips like this are what she is made for, and she has nice tactical speed, so if she bounces back to her best second off the layoff, she shapes as a contender.
5. Vahva: The defending champion has had a rough run of things since winning this race last year. She was third behind Society as the favorite in the Ballerina (G1) at Saratoga, and then a no-threat eighth in the Breeders’ Cup Filly and Mare Sprint despite being well bet. The Cherie DeVaux trainee freshened up for six months before returning on the Derby City Distaff, where she was well placed early but weakened to seventh. She may bounce back—her flop at Churchill came in the slop, and she is undefeated over fast Churchill ground. But it’s not a given after a few flat races, and the price won’t be much.
6. Marmalade Skye: Running Marmalade Skye in the Chicago Stakes seems like a case of striking while the iron is hot for trainer David Jacobson—this is her 20th start, and her first try under stakes conditions, much less graded. She was a $50,000 claim to the barn last November, out of a fourth-place effort at Churchill Downs. Since then, however, she has won four of six, including a $50,000 claimer at 6 ½ furlongs at Churchill Downs two back, and an allowance optional claimer (for which she was in for the $80,000 tag) going six furlongs there last out. Her speed figures suggest that she needs to run a career best to be a threat, but she is tactical, she keeps showing up, and 6 ½-furlong form bodes well at seven.
7. Harbor Springs: Hopes were obviously high for her, as she was second in the Beaumont (G2) last year in only her third career start. However, it took her a while to put things back together after that. She got back in winning form three back at Churchill, in a first-level allowance at 6 ½ furlongs last November, and then followed that up with a second-level win at Fair Grounds in February. She will need a step up from that form, though, and will be best served in this race if she sticks to the stalking style she showed two back, and not the more midpack-to-closing form she shows more often.
8. Pigalle: Freshened since November, Pigalle looked good when winning a third-level allowance at Churchill Downs on May 30. That was over 7 ½ furlongs on the slop, meaning she cuts back and switches to a fast track for this. Even though she is undefeated on a wet track, she is also consistent on dry. The cutback in distance is a slight concern as she usually goes the mile (both one turn and two turns), though she did miss by a head (albeit against starter-allowance types) in her only try at this trip. In short, this tactically versatile mare has some price appeal.
9. My Mane Squeeze: She is a Grade 2 winner at Churchill Downs already, winning the Eight Belles (G2) last year over this distance on a sloppy track. This seven-furlong specialist also won the Dogwood (G3) over this course and distance on a dry track, proving she doesn’t need rain—a positive, as Saturday is supposed to be dry. Her two starts this year have been good: she was third in the Madison (G1) in her first try against older, and even though she was defeated in the Ruffian last out, she had some trouble, and the one-mile trip may have been too long. Cutting back to her best trip, expect her to run well.
10. Claret Beret: Claret Beret makes her stakes debut after a varied 12-race career through which she has won five races. She has moved around between turf and dirt, with dirt proving her better surface. She has won twice at two turns and twice at one—to her credit, the two one-turn victories came at seven furlongs and a one-turn mile, meaning this kind of track configuration suits. There’s a concern that she bounces off the huge race she won last out, a 19 ¾-length win in a handicap at Gulfstream first off a two-month break. But, even with class to prove, wins at Ellis, Keeneland, and Oaklawn show she’s not only a Gulfstream Park horse.
11. Zeitlos: Toss the Breeders’ Cup Filly and Mare Sprint, and her form has been strong for the last year. She got a nice long freshening after that and came back a winner in the Skipat on Preakness day. Her form last year suggests she can move forward second off the lay. The big question is whether Zeitlos wants to run this long, as she is winless at the distance. But, she was third in her only start over the trip that didn’t come in Breeders’ Cup company, and she won the 6 ½ furlong Open Mind over the classy Positano Sunset last year. She also gets Flavien Prat in the irons, always a positive on a big stage.

Chicago Stakes FAQ

Q: When is the Chicago Stakes?

A: The Chicago Stakes is scheduled for Saturday, June 21, 2025, at 10:11 p.m. ET.

Q: Where is the Chicago Stakes?

A: The Chicago Stakes is held at Churchill Downs in Louisville, Kentucky.

Q: Which trainer has the most wins in the Chicago Stakes?

A: Seven trainers have won the Chicago Stakes twice: Donald Winfree (1986, 1987), Frank Brothers (1989, 2001), D. Wayne Lukas (1992, 1995), Philip England (1996, 2000), Bill Mott (2006, 2011), Jonathan Sheppard (2009, 2010), and Bret Calhoun (2013, 2017). Lukas, Mott, and Calhoun are still active but none have an entrant in the 2025 edition.

Among trainers with horses in the 2025 edition, those who have won this race before include Steve Asmussen, who trains Zeitlos; Brad Cox, who trains Emery; and Cherie DeVaux, who trains defending champion Vahva.

Q: Who is the favorite for the Chicago Stakes?

A: The morning-line favorite for the Chicago Stakes is rail-drawn Emery at 5-2. Vahva is a close second choice at 3-1. Expect both to take money – Vahva has the back class, though Emery brings the better recent form.

Q: Who is the best Chicago Stakes jockey?

A: Three jockeys, all retired, have won the race three times: Pat Day, Craig Perret, and Rene Douglas. Among jockeys entered in the 2025 edition, those who have won it before include Brian Hernandez, Jr., who rides Brightwork; and Irad Ortiz, Jr., who returns to ride Vahva just like last year.

Q: Who won the Chicago Stakes in 2024?

A: Vahva won the 2024 Chicago Stakes for trainer Cherie DeVaux and jockey Irad Ortiz, Jr. The same team is behind Vahva’s title defense attempt in 2025.

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