BEST DATE NEWS

Aug. 6, 2026: Best Date News Volume #190

Welcome to Best Date News, your go-to guide for what's happening in Chicago! This week, we're diving into the Chicago Ducky Derby, Divvy Bikes, Six Flags Great America, Portillo’s, music festival lineups, Holiday Touchdown: A Bears Love Story, weekend activities and much more.

Via National Day Calendar

Aug. 6: National Holidays

  • National Root Beer Float Day

  • National India Pale Ale (IPA) Day

  • National Fresh Breath Day

  • National Gossip Day

  • National Wiggle Your Toes Day

Sponsored by our friends at Ravinia

Via Ravinia

Take the Train to Ravinia for Free

  • Ravinia: If you've been thinking about going to Ravinia this summer, here's something you might not know: Your concert ticket also serves as your Metra ticket. On the day of your show, you can ride the Union Pacific North Line from Chicago's Ogilvie Transportation Center to Ravinia and back completely free.

  • Ravinia is a historic outdoor music venue in the Chicago suburb of Highland Park that's best known for its lawn picnics and incredible summer concert lineup. But if packing a picnic sounds like too much work, you can also show up empty-handed and enjoy great restaurants, bars and concessions throughout the park.

  • During the summer concert season, Union Pacific North trains make a stop at Ravinia Park, located just steps from the venue's front gate. It's one of the easiest ways to skip the traffic, parking and picnic prep.

  • Upcoming shows this month include Ricky Martin, Chance the Rapper, Hugh Jackman, Alabama Shakes, Brian McKnight & Gladys Knight, Joe Bonamassa, Miranda Lambert and many more. See the full concert lineup and start planning your next Ravinia night out.

Chicago News

  • Chicago Ducky Derby: The annual Chicago Ducky Derby takes place today. Up to 88,000 rubber duckies will be poured into the Chicago River and race to the finish line to win prizes. Splashdown is today at 1 p.m. from the Columbus Drive Bridge. The event is a fundraiser supporting Special Olympics Illinois. You'll find more information below on how you can adopt a duck and support the cause.

  • Divvy Bikes: Getting around Chicago's lakefront just got a little easier. The city has installed five new Divvy stations near popular destinations including North Avenue Beach, Lincoln Park Zoo and DuSable Lake Shore Drive. The expansion comes as Divvy recorded its busiest month ever, with more than one million rides in July. Chicago is now on pace to surpass last year's record of six million rides.

  • Six Flags Great America: Six Flags Great America has announced Camp Timber Trail, an all-new family adventure opening in 2027 as the first phase of a multi-year transformation of the Gurnee amusement park. One of the largest family-focused investments in the park's history, the new area will feature nine attractions, including three brand-new experiences and the Midwest's longest, tallest and fastest suspended family coaster. Guests can also expect new dining, shopping and park-wide improvements over the next several years.

  • Stella’s Diner: Stella's Diner has officially closed after more than 60 years in Lakeview. Ann Sather has purchased the restaurant at 3042 N. Broadway and plans to relocate its current Broadway location at 3415 N. Broadway into the space after renovations are complete, a process expected to take a few months. Stella's owner said the sale had been in the works for months and was unrelated to the diner's recent temporary closure following health code violations.

  • Wishbone: After 36 years, Wishbone has announced it will permanently close its beloved West Loop breakfast and brunch restaurant at 161 N. Jefferson St. While an exact closing date hasn't been set, the Southern comfort food spot hopes to remain open through the end of August, giving longtime fans one last chance to stop by before it says goodbye.

Via Portillo’s

Just For Fun

  • Portillo’s: Portillo's has introduced a new Dr Pepper Shake for a limited time. The thick, creamy shake is blended with real Dr Pepper flavor and is available through September while supplies last. You can also order it as a Dr Pepper Cake Shake, which blends in a slice of Portillo's famous chocolate cake. In other Portillo's news, the company announced it has laid off 18% of its staff at its Oak Brook headquarters.

  • Music Lineups: Two of Chicago's biggest music festivals released their 2026 lineups today. Riot Fest unveiled its daily schedule for Sept. 18-20 in Douglass Park, while the free Chicago House Music Festival announced its lineup for Aug. 27-30 in Millennium Park. If you're planning to attend either festival, now's the time to see who's performing and start planning your weekend.

  • Holiday Touchdown: Hallmark has announced the cast and release date for its upcoming Chicago Bears holiday movie, Holiday Touchdown: A Bears Love Story. The film, which was shot across the Chicago area this summer, premieres Saturday, Oct. 17, and features cameo appearances from Bears head coach Ben Johnson, Colston Loveland, Cole Kmet, Mike Singletary, Charles "Peanut" Tillman, Dan Hampton and mascot Staley Da Bear.

  • New Home Alone Movie: Chicago's favorite holiday movie could be getting a sequel. According to PEOPLE, Macaulay Culkin has pitched a new Home Alone film to Disney that would bring him back as Kevin McCallister. The original movie was filmed throughout the Chicago area, including the iconic McCallister home in Winnetka, though Disney has not officially announced the project.

  • Irving Park Garage Sale: Treasure hunters won't want to miss the Irving Park Community Garage Sale on Saturday, Aug. 8, from 8 a.m. to 4 p.m. More than 120 homes across the neighborhood will take part, offering antiques, furniture, kitchenware, books, tools and plenty of unique finds. An interactive Google Map makes it easy to plan your route and find participating homes.

Sponsored by our friends at Special Olympics Illinois

Via Special Olympics Illinois

Last Chance to Adopt a Duck for the Chicago Ducky Derby

  • Special Olympics Illinois: One of Chicago's most beloved summer traditions returns this afternoon as thousands of rubber ducks splash down into the Chicago River and race to the finish line in the annual Chicago Ducky Derby benefiting Special Olympics Illinois.

  • You can still take part by adopting one (or more) of the race's rubber ducks starting at just $10 before they hit the water this afternoon. Every adopted duck is entered into the race, with one lucky duck winning its adopter a brand-new Chevy Trax. Even better, every adoption helps provide free year-round sports training and competition for Special Olympics Illinois athletes.

  • The ducks are released from the Columbus Drive Bridge at 1 p.m. Whether you're planning to attend in person or cheer the ducks on from afar, it's one of Chicago's most unique summer traditions.

  • In addition to adopting a single duck for just $10, there are also four discounted package options if you'd like to increase your chances of winning. This is your last chance to help Special Olympics Illinois reach its goal of 88,000 ducks adopted this year while supporting thousands of athletes across Illinois.

Via Bud Billiken Parade

Weekend Plans

  • Bud Billiken Parade: The 97th annual Bud Billiken Parade steps off at 10 a.m. on Saturday, Aug. 8, traveling from 39th Street and Dr. Martin Luther King Jr. Drive to 51st Street before ending with a free Back-to-School Festival in Washington Park. It's the nation's largest African American parade and one of Chicago's most celebrated community traditions. Expect colorful floats, marching bands, dance teams and community groups throughout the parade, with the festival continuing there until 4 p.m.

  • Northalsted Market Days: One of Chicago’s biggest street festivals returns this weekend in Lakeview. Northalsted Market Days runs Aug. 7 to 9 with live music on four stages, 250+ vendors, food, dance exhibitions, drag performances and more. Hours are Friday 4 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.

  • Lincoln Square Cat Tour: The first-ever, free Lincoln Square Cat Tour takes place Saturday, Aug. 8, from 3 to 5 p.m. Participants are invited to explore the neighborhood while meeting local feline residents and celebrating the cats that help make the community so special. You can also view an interactive Google Map featuring all of the participating cats and tour routes before you go.

  • LatiNxt: Navy Pier hosts the free, all-ages LatiNxt Festival this Saturday, Aug. 8 and Sunday, Aug. 9, celebrating contemporary Latine music, art, culture and community. The two-day event features three stages of live music and DJs, dance performances, local art and cultural experiences showcasing artists from across the Latin American diaspora. You'll also find a mercadito with local artisans and small businesses along the lakefront.

  • Ravenswood Feel Good Fest: On Saturday, Aug. 8, the inaugural Ravenswood Feel Good Fest takes over Clark Street and Sunnyside Avenue from 11 a.m. to 5 p.m. with a free, family-friendly celebration of wellness, arts, sustainability and community. Enjoy live music, dance and fitness demonstrations, local food and drinks and a market featuring neighborhood artisans, small businesses and community organizations.

Poll Question of the Week

In honor of National Root Beer Float Day and Portillo's new shake, which would you rather have?

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Last Newsletter's Poll Results

Poll Results: Last week, we asked which T-Mobile Stage headliner at Lollapalooza you were most excited about. Here's how you voted:

  • 50%: Olivia Dean

  • 24%: Lorde

  • 21%: Tate McRae

  • 5%: Charli xcx

Sunrise & Sunset in Chicago

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

  • Sunrise: 5:49 a.m. (7 minutes later)

  • Sunset: 8:02 p.m. (8 minutes earlier)

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