The Closing Stretch of Chicago Summer

BEST DATE NEWS

Aug. 21, 2025: Best Date News Volume #140

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about the Concourse D expansion at O’Hare, Derrick Rose’s jersey retirement, Christkindlmarket Wrigleyville, John Stamos at Riot Fest, viral Chicago sports moments this week and more!

Aug. 21: National Holidays

• National Spumoni Day

• National Senior Citizens Day

• National Brazilian Blowout Day

• National Hazy IPA Day

• National Internet Self-Care Day

Sponsored by our friends at Cleveland Kitchen

Cleveland Kitchen x GG’s Chicken Shop Pop-Up

• Pickle Pop-Up Party: This Saturday, Aug. 23, from 2–4 p.m., Cleveland Kitchen, the makers of fresh, flavorful and gut-healthy fermented foods, is hosting a dill-icious, family-friendly Pickle Pop-Up Party at GG’s Chicken Shop (3325 N Southport Ave #2).

• It’s free to attend, and guests will have the opportunity to sample products including Cleveland Kitchen favorites like Hot Honey Jalapeños, Pickled Red Onions and probiotic-rich sauces.

• The unique pop-up will also have exclusive menu items available for purchase like the limited-time “Kimchi Curious” sandwich (available Aug. 18–24) and specialty cocktails like the Kimchi Pickle Bloody Mary and Dill Pickle Martini, with proceeds going to a local charity.

• There will be a special surprise for the first 100 people (with purchase), co-branded merchandise giveaways and family-friendly activities like a pickle-themed Plinko game with prizes and a kids’ coloring station, so bring the whole family out to Southport this weekend!

Chicago News

• O’Hare Expansion: Ground has officially broken on Concourse D, a $1.3 billion satellite terminal at O’Hare that will add 19 new gates and connect directly to Concourse C. It’s the airport’s first major concourse build since 1993, arriving after nearly a decade of negotiations and delays. Designed with soaring glass, more natural light and open, modern architecture, the new concourse is expected to wrap by late 2028.

• Derrick Rose: The Chicago Bulls announced this morning that they will retire Derrick Rose’s No. 1 jersey on Jan. 24, 2026, during a postgame ceremony at the United Center when the Bulls host the Boston Celtics. Rose will become just the fifth player in franchise history to receive the honor. Fans can celebrate throughout the season at four games where the Bulls will give away collectible Rose figurines at the United Center.

• Christkindlmarket: The Wrigleyville Christkindlmarket is back this year after sitting out last season for the NHL Winter Classic and other events. All three German holiday markets return for 2025, with Downtown Chicago at Daley Plaza, Aurora’s RiverEdge Park and Wrigleyville at Gallagher Way. The Wrigleyville market runs November 23 through December 31, helping ease the crowds at the flagship Daley Plaza location.

• Riverfront Restaurant: DineAmic Hospitality is bringing a new Mediterranean restaurant to the riverfront in 2026 as part of a $37 million renovation at 300 N. LaSalle. The project, located below Chicago Cut Steakhouse, will also include a private lounge for events and a coffee shop. DineAmic, the group behind Prime & Provisions, Siena Tavern and Barrio, plans indoor and outdoor seating to make the most of the river views.

• Starbucks Closings: Starbucks will phase out its pickup-only stores by 2026, with about 80 to 90 locations nationwide closing or being converted into traditional cafés. That includes five Chicago locations and 11 total in Illinois, the third most of any state after California and New York. See the locations that are closing.

Just For Fun

• Stamos at Riot Fest: After years of Riot Fest campaigning, John Stamos is finally set to join the Beach Boys on drums at the music festival on Sept. 20. His appearance came with demands, including a Chicago pizza in his honor, and local spots appear to be delivering. Giordano’s rolled out The Stamos Supreme with spinach, artichoke and feta, while Max & Issy’s is serving John Stamos’ Big Fat Greek Sausage pie during Riot Fest weekend, Sept. 19–21.

• Work From Wrigley: A Cubs fan went viral this week for setting up his laptop in the Wrigley Field bleachers. MLB dubbed it “Ferris Bueller’s Remote Day,” and baseball fans couldn’t stop laughing at the sight.

• Love Island: The Season 7 reunion episode of Love Island airs Monday, Aug. 25, bringing the cast back together to share updates, revisit relationships and stir up more drama. Chicago fans can catch it at local watch parties, including Parlay at Lincoln Park, Bar La Rue and Theory.

• Colston Loveland: From Love Island to Loveland, the Chicago Bears rookie tight end captured hearts this week with his viral performance of Mario’s 2004 hit “Let Me Love You.” For context, it’s tradition that rookies are often asked to sing in front of teammates during training camp. Here is what Colston had to say about it, plus Mario’s reaction.

• Chicago Cocktail Bars: Eater Chicago put together a list of the best places to drink cocktails in the city right now. Highlights include Friends of Friends in West Town, Pilot Project Brewing’s new Wrigleyville rooftop and cocktail lounge and hidden speakeasy Clandestino in River North.

Weekend Plans

• Weekend Concerts: It’s a packed weekend of live music across Chicago. Lenny Kravitz kicks things off at Ravinia tonight, followed by Maren Morris Friday and John Legend Saturday and Sunday. Lil Jon hits Tao Friday, Benson Boone plays the United Center Saturday, while Sunday brings Lil Wayne to Credit Union 1 Amphitheatre and Simple Plan to Huntington Bank Pavilion at Northerly Island.

• House Music Festival: The Chicago House Music Festival and Conference takes over Millennium Park this weekend, celebrating the city’s homegrown genre that shaped dance music worldwide. Free performances run Saturday, Aug. 23, from 1–9 p.m. at the Pritzker Pavilion with multiple stages of DJs, while the conference and dance workshops kick off Friday, Aug. 22, at the Chicago Cultural Center.

• Food & Drink Festivals: It’s a big weekend for eating and drinking in the city. Lakeview Taco Fest runs Friday through Sunday on Southport with taco vendors and live music, Pizza City Fest brings together the area’s best pizza makers Friday through Sunday, Sangria Festival Chicago pours colorful cocktails Saturday and Sunday in Humboldt Park and EEEEEATSCON Chicago takes over The Salt Shed Saturday and Sunday with bites from top local and national restaurants.

• Chicago Triathlon: The 2025 Chicago Triathlon takes over the lakefront Aug. 23–24 with thousands of athletes swimming in Lake Michigan, biking through downtown and running along the shoreline. It’s one of the world’s largest and most accessible triathlons, and spectators can catch the action at Monroe Harbor for the swim, downtown bridges during the bike leg or Grant Park for the finish.

• Chicago International Boat Show: The Chicago International Boat Show takes over Navy Pier Aug. 21–24 with more than 150 boats and watercraft on display at the new marina. Expect luxury yachts, adventure gear, live music, fireworks and family-friendly programming, making it the Midwest’s biggest celebration of summer on the water.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked if you planned on watching the Chicago Air & Water Show. It was pretty evenly split. 47% said yes and 53% said no. If you went, we hope you had a nice time!

Sunrise & Sunset in Chicago

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

• Sunrise: 6:05 a.m. (8 minutes later)

• Sunset: 7:41 p.m. (10 minutes earlier)

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