Chicagohenge is Back

BEST DATE NEWS

Sept. 18, 2025: Best Date News Volume #144

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about Chicagohenge, the Chicago River Swim, this week’s big concert announcements, The Summer I Turned Pretty series finale, Oktoberfests and other things happening this weekend and more!

Sept. 18: National Holidays

• National Cheeseburger Day

• National First Love Day

• National Rice Krispie Treat Day

• National Respect Day

• National Pawpaw Day

Sponsored by our friends at Naperville Artisan Market

Free Outdoor Market this Weekend

• Naperville Artisan Market: The twice-a-year Naperville Artisan Market returns this weekend for their fall market. This fun two-day, outdoor market is free to attend, is both kid and dog friendly and has plenty of free parking.

• The fall market brings together 100 of the best artisans from around the Midwest specializing in areas like food, fashion, art, home goods and more. It celebrates the ingenuity of independently owned, small businesses who channel their passions into creating one-of-a-kind products.

• The next Naperville Artisan Market won’t take place until spring of next year, so don’t miss this one if you are looking to go! If you can’t make it though, there will also be an Oak Brook Artisan Market taking place in October.

• You can find it at 2135 CityGate Lane in Naperville Saturday, Sept. 20 and Sunday, Sept. 21 from 10 a.m. to 4 p.m. It takes place within CityGate Centre, a 30+ acre walkable, urban oasis with restaurants right nearby. You can RSVP for free if you want to let them know you’re coming.

Chicago News

• Chicagohenge: The famous twice-a-year Chicagohenge is back! On Monday, Sept. 22 the sun will align perfectly with Chicago’s east and west streets during the autumn equinox, creating one of the city’s best photo moments. You can catch it along corridors between Kinzie and Madison, with top views at Washington and Michigan by Millennium Park. Sunset is at 6:47 p.m., so arrive early for the best shot. You can also catch it nearly perfect this weekend on Sept. 20 and 21, depending on the weather. Here’s why it only happens twice a year.

• Chicago River Swim: The Chicago River Swim is making history this weekend as the first open-water race in the river in nearly 100 years. Taking place Sunday, Sept. 21 at 7 a.m., the event is organized by local nonprofit A Long Swim to raise money for ALS research. The 2025 course covers an 800-meter stretch between Wolf Point and the State Street Bridge, with swimmers competing in both 1-mile and 2-mile distances. Around 400 athletes, including Olympians, are set to dive in for the historic race.

• Concert Announcements: Ed Sheeran just announced this morning that he will bring his Loop Tour to Soldier Field on June 27, 2026, with artist presale on Sept. 23 at 9 a.m. (sign up) and general tickets on sale Sept. 26 at 10 a.m. Cardi B is bringing the Little Miss Drama Tour to the United Center on Saturday, March 21, with artist presale open through Sunday, Sept. 21 at 11:59 p.m. Two Friends will premiere Big Bootie Mix, Vol. 27 live in Chicago at Huntington Bank Pavilion on Saturday, May 16, promising their biggest show yet. Use code BACK2CHI for the presale happening right now. Chicago’s 2026 concert calendar is already stacking up to be huge.

• Sports Illustrated Hotel: Travel + Leisure Co. is bringing its Sports Illustrated Resorts brand to Chicago, converting the Virgin Hotel in the Loop into a 250-room property with sports-inspired design, a coffee shop, full-service restaurant and lively sports bar. The hotel will remain open during construction, with the bar and restaurant set to welcome guests this winter and full completion expected in late 2026. Chicago will be the brand’s third location, following Tuscaloosa and Nashville.

• Roots South Loop: Roots Handmade Pizza announced it will soon close its South Loop location, with the final day of service on Sunday, Oct. 5. The spot opened five years ago and became known for its awesome rooftop and Quad City-style pies. Roots will continue to operate its original West Town location, where fans can still enjoy all of the menu favorites.

Just For Fun

• TSITP Movie: Did you watch The Summer I Turned Pretty series finale?! If you did and you’re sad that Belly’s story is over, there’s some good news. Author Jenny Han just announced that The Summer I Turned Pretty is being made into a movie! Stars Lola Tung (Belly) and Christopher Briney (Conrad) will return, and the film will officially close out the trilogy. The only catch? It likely won’t hit screens until 2027. Get all the details.

• Cubs Clinch Playoffs: The Cubs officially clinched a playoff spot yesterday after defeating the Pirates 8–4 in Pittsburgh (watch the hype video). The postgame celebrations were absolute cinema, and the vibes are high right now! The team has made a strong late-season push winning seven of their last eight games, and they will look to carry that momentum into October as Wrigley Field prepares to host playoff baseball once again.

• Christkindlmarket Mugs: The 2025 Christkindlmarket mugs and stein were just officially revealed. Take a look at the 2025 collection. This year’s heart-shaped mug comes in festive red with local Chicago landmarks and a classic market scene, while the nonalcoholic mug features gingerbread figures in traditional dress on a brown base with a red handle and icing detail. The annual beer stein debuts a new shape with a white finish and a night scene of the market, complete with the Christkind and golden starry sky.

• Open House Chicago: The Chicago Architecture Center has just released the full site list for Open House Chicago 2025, taking place Oct. 18 and 19. More than 200 buildings will open their doors for free during the annual festival, offering access to places of architectural, historical and cultural significance while spotlighting businesses, organizations and creative leaders in Chicago’s neighborhoods.

• Labubu Pop-Up: Gangnam Market Chicago is hosting a Labubu Pop-Up on Saturday, Sept. 20 and Sunday, Sept. 21 from 11 a.m. to 8 p.m. The event will feature all versions of Labubu collectibles, exclusive clothing from Build Your Collectibles, blind box drops like Sonny Angel, giveaways, surprise mascot appearances and even live Labubu tattoos from LA artist Crybabyhunter. Guests can also enjoy food, beverage and liquor demos throughout the store all weekend.

Weekend Plans

• Chicago Live!: Navy Pier transforms into a massive stage this weekend for the fifth anniversary of Chicago Live!, the Midwest’s largest free performing arts festival. More than 100 Chicago-based artists and organizations will perform across five stages and even by boat during the two-day celebration. On Saturday, Rock and Roll Hall of Famer Buddy Guy, age 89, headlines at 9 p.m. before a fireworks finale at 9:30 p.m. The free festival runs Saturday, Sept. 20 and Sunday, Sept. 21.

• Old Town Oktoberfest: Don’t miss the debut of the Old Town Oktoberfest on Wells Street this weekend! This Bavarian celebration aims to bring back the neighborhood’s German roots with bratwurst, pretzels and German beer, plus live music from traditional bands and local favorites. Festivalgoers can watch football on the big screen and join stein-holding contests for a chance to win prizes. The free event runs Friday, Sept. 19 from 5 to 10 p.m., Saturday, Sept. 20 from 11:30 a.m. to 10 p.m. and Sunday, Sept. 21 from 11:30 a.m. to 8 p.m.

• Oktoberfest with the Cubs: Wrigleyville is also going Bavarian this weekend with the first-ever Oktoberfest with the Cubs at the Toyota Camry Lot, 1126 W. Grace St. The three-day event runs Friday, Sept. 19 from 4 to 10 p.m., Saturday, Sept. 20 from 11 a.m. to 10 p.m. and Sunday, Sept. 21 from 12 to 7 p.m. Expect beer tents, bratwurst and pretzels, plus live music, DJs and carnival rides. Highlights include a ceremonial keg tap, Dachshund parade, Kinderfest for kids and stein-holding contests. Tickets are $15 for general admission or $75 for VIP and kids 10 and under are free. The rookies are Oktoberfest ready.

• Englewood Jazz Festival: The 26th Annual Englewood Jazz Festival takes over Hamilton Park Sept. 18–20, honoring the 60th anniversary of the Association for the Advancement of Creative Musicians. Founded by saxophonist Ernest Dawkins, the festival has grown into a South Side tradition that blends creative expression with community spirit. This year features AACM legends alongside rising artists, with performances indoors on Thursday and Friday and outdoors on Saturday, rain or shine. Admission is free.

• West Loop Music & Art Fest: Fulton Market comes alive this weekend for a five-block celebration of art and music. By day, browse 100+ artists and makers with family-friendly activities and interactive crafts. As the sun sets, the West Loop Music & Art Fest turns into a lively street party with food trucks, DJs and live bands. Music runs Saturday, Sept. 20 from 2 p.m. to 10 p.m. and Sunday, Sept. 21 from 2 p.m. to 9:30 p.m.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked which player from the 2016 Chicago Cubs World Series team was your favorite. Your top three in order were:

• First: Anthony Rizzo

• Second: Kris Bryant

• Third: Javier Báez

Sunrise & Sunset in Chicago

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

• Sunrise: 6:34 a.m. (8 minutes later)

• Sunset: 6:54 p.m. (12 minutes earlier)

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