It's Chicago Ducky Derby Day

BEST DATE NEWS

Aug. 7, 2025: Best Date News Volume #138

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about the Chicago Ducky Derby, Lake Shore Drive possibly being moved underground, the last day of 8 p.m. sunsets in Chicago, what to do this weekend and more!

Aug. 7: National Holidays

• National IPA Day

• National Purple Heart Day

• National Lighthouse Day

• National Cycle to Work Day

• National Raspberries n’ Cream Day

Sponsored by our friends at Chicago Gourmet

Chicago Gourmet 2025

• Step Up to the Plate: Tickets for Chicago Gourmet 2025 are now on sale. If you’ve never been, it’s one of the top culinary festivals in the country, and it all takes place in downtown Chicago. A must-attend for food lovers.

• The four-day food and drink festival celebrates Chicago’s world-class culinary scene and brings together top chefs and restaurants for a series of signature events on the Harris Theater Rooftop Terrace at Millennium Park.

• This year’s theme is “Step Up to the Plate,” with sports-inspired activations happening across the city. Events run from Sept. 25–28 and include Tacos & Tequila, Hamburger Hop, Grand Cru, Asian Late Night Market, Somm Sessions and Rise & Shine Gourmet.

• These events sell out every year, so if you’re thinking about going, grab your tickets soon. See the full lineup and get tickets.

Chicago News

• Chicago Ducky Derby: The annual Chicago Ducky Derby takes place today. Up to 80,000 rubber duckies will be poured into the Chicago River and race to the finish line to win prizes. The event is a fundraiser that supports Special Olympics Illinois. You can still adopt a duck for the race. There are less than 1,000 left! Splashdown is today at 1 p.m. at the Columbus Bridge.

• Lake Shore Drive: Big changes could be coming to Lake Shore Drive near Grant Park. The Chicago Park District recently released a new vision for the area that includes narrowing parts of the road and putting it underground. The idea is to extend Grant Park to the lakefront by improving pedestrian access near Buckingham Fountain. Will this massive change actually happen? It’s too early to tell, but you can check out the full proposal and share feedback through the end of August.

• Chicago Bars: One bar is closing, another just got a second life. After 30 years of whiskey, wings and rooftop brunches, Twisted Spoke is shutting down for good. The West Town favorite will serve its last round on Aug. 31, so there are only four Whiskey Wednesdays and four rooftop brunches left. Meanwhile in Old Town, Burton Place just reopened under new local ownership and will now stay open until 4 a.m. daily and 5 a.m. on Saturdays.

• 8pm Sunsets: If you needed a reason to start taking advantage of summer before it’s over, this is it. Tonight is Chicago’s last 8 p.m. or later sunset until May 12, 2026. That’s 278 days from now. The good news? It’s supposed to be beautiful out, so get out there and make the most of it.

• Ventra: A new and improved Ventra system is on the way. The CTA is testing upgraded readers at select rail stations and buses for the first time in over 10 years. A full system overhaul is in the works, with a monthlong pilot planned for this fall and winter to gather rider feedback.

Just For Fun

• Riot Fest Aftershows: Tickets for this year’s late night Riot Fest Aftershows went on sale at 10 a.m. today. You can catch acts like Sex Pistols, The Front Bottoms, Senses Fail and Texas Is the Reason playing at venues across Chicago after the festival wraps each night. These shows can sell out fast so if you’re looking to go, consider grabbing your tickets soon.

• Doechii: Fresh off her Lollapalooza performance, Doechii just announced her Live From the Swamp Tour. The first stop is right here in Chicago on Oct. 14. If her set last weekend was any preview, this show is going to be a lot of fun.

• Best Tavern-Style Pizza: Deep dish might get the national spotlight, but thin crust is what locals actually eat. Eater just dropped its updated list of Chicago’s Best Tavern-Style Thin-Crust Pizza Restaurants. From new spots to neighborhood staples, these are the places they say are worth knowing.

• Chicago Apartment: This West Town apartment might have the most unhinged layout in the city. It’s a newly renovated three bed, three bath for $3,900 a month with one major catch. It’s on the first floor with floor to ceiling windows right at street level. You are basically living in a fishbowl. You need to see this layout to believe it.

• Streaming Shake Up: If you watched Lollapalooza on Hulu this past weekend, you may have been among the last to do it that way. Disney is phasing out the standalone Hulu app and fully merging it into Disney Plus by early 2026. You’ll still need a separate subscription, but everything will live in one place moving forward.

Sponsored by our friends at Hideaway Brew Garden

Bikini Bottom Bar

• Hideaway Brew Garden: Who lives in a beer garden under the sea? Hideaway Brew Garden! For a limited time, at least. The suburban beer garden is going full SpongeBob mode with its first-ever Bikini Bottom Bar takeover.

• Hideaway Brew Garden is a live music and entertainment venue in Hoffman Estates that hosts free outdoor shows every Thursday through Sunday. Check out the rest of the summer schedule.

• The Bikini Bottom Bar takeover runs Aug. 14–24 (during regular open days and hours) and will feature SpongeBob-themed cocktails, underwater vibes, photo ops and plenty of nautical nonsense.

• Entry is free and no tickets are needed. Just show up and soak up the Bikini Bottom fun. You can bring lawn chairs, grab a picnic table or upgrade your night by renting one of their themed private spaces like The Office, Friends, Barbie or 2d Restaurant.

Weekend Plans

• Market Days: One of Chicago’s biggest street festivals returns this weekend in Lakeview. Northalsted Market Days runs August 8 to 10 with live music on four stages, drag performances, dance shows, food and over 250 vendors. Hours are Friday 5 to 10 p.m. and Saturday and Sunday 11 a.m. to 10 p.m. It all takes place along Halsted from Belmont to Addison with a suggested $20 donation.

• Bud Billiken Parade: One of Chicago’s most iconic summer traditions returns this Saturday, Aug. 9. The 96th annual Bud Billiken Parade runs down MLK Drive from 35th to 51st Street starting at 10 a.m., ending with a community festival in Washington Park. It’s the largest African American parade in the country, with this year’s theme, “Road to 100 Years,” celebrating culture, education and back to school fun.

• Chicago Bears: The Bears kick off their preseason at home this Sunday, Aug. 10 with a noon game against the Dolphins at Soldier Field. Tickets on the secondary market currently start around $40. At training camp last week, the team made a 13-year-old’s dream come true by hosting him at practice and letting him break down the huddle.

• Maxwell Street Market: The iconic Maxwell Street Market is back this Sunday, Aug. 10, for its only August date (the next one is Sept. 14). You’ll find food, crafts, vintage finds and live music from 10 a.m. to 3 p.m. on Maxwell Street between Halsted and Union. Admission is free.

• LIV Golf Chicago: Professional golf returns to the suburbs this weekend as Bolingbrook Golf Club hosts LIV Golf Chicago from August 8 to 10. Gates open at 9 a.m. and kids 12 and under get in free. Beyond the golf, expect live music, interactive fan zones and a full tournament atmosphere with a $20 million purse on the line.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked you which Lolla headliner you thought was best. Here is the order of who got the most overall votes:

• 44%: Sabrina Carpenter

• 22%: Olivia Rodrigo

• 16%: Rüfüs Du Sol

• 7%: Twice

• 7%: A$AP Rocky

• 4%: Tyler, The Creator

Sunrise & Sunset in Chicago

Here is today’s outlook in Chicago (compared to last week):

• Sunrise: 5:50 a.m. (7 minutes later)

• Sunset: 8:01 p.m. (8 minutes earlier)

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