BEST DATE NEWS

Sept. 17, 2026: Best Date News Volume #196

Welcome to Best Date News, your go-to guide for what's happening in Chicago! This week, we're diving into Chicagohenge, the Chicago River Swim, Google's new Thompson Center designs, Riot Fest, Harry Styles, weekend events and much more.

Via National Today

Sept. 17: National Holidays

  • National Pet Bird Day

  • National Constitution Day

  • National Monte Cristo Day

  • National Professional House Cleaners Day

  • National Apple Dumpling Day

Sponsored by our friends at Naperville Artisan Market

Via Naperville Artisan Market

This Weekend: Naperville Artisan Market

  • Naperville Artisan Market: The twice-a-year Naperville Artisan Market returns this weekend for its fall market! This free outdoor event is kid and dog friendly, with plenty of free covered parking and indoor amenities.

  • This will be its biggest market at CityGate Centre yet, featuring 120+ local and Midwest artisans showcasing everything from food and fashion to home goods, art and more. It's a great opportunity to shop small and discover unique products from independently owned businesses.

  • There are also plenty of options for food and drinks right at CityGate Centre, including coffee, cocktails and several restaurants where you can grab breakfast, lunch or dinner before or after exploring the market.

  • The market takes place Saturday, Sept. 19 and Sunday, Sept. 20 from 10 a.m. to 4 p.m. at 2135 CityGate Lane in Naperville. It's located within the 30+ acre CityGate Centre, with restaurants just steps away!

Chicago News

  • Chicagohenge: One of Chicago’s coolest photo opportunities is almost here! Chicagohenge returns around the autumn equinox on Tuesday, Sept. 22, when the sun aligns with the city’s east-west street grid at sunset. Weather permitting, you can catch the spectacle from Sept. 19–22 along streets between Kinzie and Madison, with one of the best viewing spots at Washington and Michigan by Millennium Park.

  • Chicago River Swim: The Chicago River Swim returns this Sunday, Sept. 20 for its second year after making history in 2025 as the first organized swim in the river in nearly 100 years! Up to 750 swimmers will compete in 1-mile and 2-mile races between Wolf Point and the State Street Bridge, starting at 6:30 a.m. The Big Jump kickoff event takes place Friday at 10 a.m., bringing together Olympians, civic leaders and the public to raise money for ALS research and youth swim education.

  • Thompson Center: Google has unveiled new renderings of the Thompson Center’s redevelopment, now delayed until 2028. The 17-story atrium will feature a cascading staircase, terraced seating, dining and retail spaces and direct CTA access. Both the atrium and plaza will be open to the public. Outside, a new 30-foot-tall sculpture called Vector will replace Monument with Standing Beast at Randolph and Clark.

  • Restaurant Openings: A few notable restaurant openings are happening across Chicago this week. Bonhomme Group is debuting its third Beatnik location in Lincoln Park alongside Lolo y Lola tomorrow, Sept. 18. Beatnik will feature Mediterranean-inspired cuisine and tropical cocktails, while Lolo y Lola is an intimate 22-seat Spanish pintxos bar. Meanwhile, Ranalli's opened a new walk-up pizza window at 2471 N. Milwaukee Ave. in Logan Square and is celebrating with free square slices Saturday from 4 to 6 p.m., while supplies last.

  • IMAX Theater: Downtown Chicago is getting an IMAX theater, with plans to upgrade one of the auditoriums at AMC River East 21 in Streeterville. The addition would give Chicago its third IMAX location, joining AMC Roosevelt Collection in South Loop and Regal City North. An opening date has not been announced, and it's unclear whether the theater will support 70-millimeter film screenings.

Via Riot Fest

Just For Fun

  • Riot Fest: One of Chicago’s biggest music festivals takes over Douglass Park this weekend, with Riot Fest bringing headliners Tool, Twenty One Pilots, Pierce the Veil, Alanis Morissette, Morrissey and Iggy Pop to the city. The three-day festival (daily schedule) also features Chicago bands Twin Peaks and Alkaline Trio, plus live weather forecasts from legendary meteorologist Tom Skilling. The ticketed event runs Friday, Sept. 18 through Sunday, Sept. 20.

  • Harry Styles: Harry Styles added three more Chicago shows to his 2027 Together, Together tour, bringing his total to five concerts at Soldier Field, and it still wasn't enough. All five shows were essentially sold out by the time tickets went on sale to the general public yesterday morning. The concerts are scheduled for May 28–29, May 31 and June 4–5, marking his first Chicago performances since 2022.

  • Chicago Bears: The Bears host the Minnesota Vikings at noon this Sunday, Sept. 20 for their highly anticipated home opener at Soldier Field. Both teams enter the NFC North matchup undefeated at 1-0, with Chicago coming off a 59-37 win over the Carolina Panthers in Week 1, with the Bears currently favored by 4.5 points. Check out the new gameday eats at Soldier Field this season.

  • Miley Cyrus: Miley Cyrus is bringing an official pop-up shop to Chicago this weekend to celebrate the release of her 10th studio album, Bass Persuades. Fans can shop exclusive merchandise, including limited-edition vinyl, alternate cover CDs and apparel. The pop-up takes place Friday, Sept. 18 and Saturday, Sept. 19 from noon to 6 p.m. at 301 W. Ohio St. in River North.

  • Flotsam River Circus: A traveling circus on a floating raft has arrived in Chicago. Flotsam River Circus features musicians, circus performers and puppeteers who travel along rivers putting on family-friendly shows. Catch the free shows at Ping Tom Memorial Park tonight, Saturday and Sunday, Centennial Park in Lincolnwood on Friday and the Chicago Riverwalk on Monday. All performances begin at 6 p.m. and last about an hour, with donations appreciated.

  • Chicago Live: Navy Pier’s Chicago Live Festival returns to Navy Pier for its sixth year as the Midwest’s largest free performing arts festival. More than 100 artists and organizations will showcase live music, dance, theater and more across five stages. Chicago native Common headlines Saturday at 9 p.m., followed by a fireworks finale. The free festival runs Saturday, Sept. 19 from noon to 9 p.m. and Sunday, Sept. 20 from noon to 6 p.m.

Via Special Events Management

Weekend Plans

  • Old Town Oktoberfest: Old Town Oktoberfest is taking over Wells Street this weekend for its second straight year, celebrating the neighborhood’s German roots with bratwurst, pretzels, German beer and live music. Festivalgoers can also enjoy big-screen football, stein-holding contests and a new dog parade on Sunday. The free event has a suggested $10 donation and runs Friday, Sept. 18 from 5 to 10 p.m., Saturday from 11 a.m. to 10 p.m. and Sunday from 11 a.m. to 8 p.m.

  • Retro on Roscoe: Roscoe Village is taking a trip back in time this weekend with Retro on Roscoe, a three-day street festival featuring live music across multiple stages, classic car shows, vintage shopping and local food vendors. The family-friendly event also features a dedicated kids’ area with games and activities. It takes place along Roscoe Street near Damen Avenue Friday, Sept. 18 from 5 to 10 p.m., Saturday from noon to 10 p.m. and Sunday from noon to 8 p.m.

  • Mag Mile Art Festival: More than 60 artists from across the country will showcase their work along Michigan Avenue this weekend as part of the Magnificent Mile Art Festival. The outdoor event features original paintings, photography, jewelry, fashion, glass art and more, with opportunities to shop directly from the artists. The free festival takes place Saturday, Sept. 19 and Sunday, Sept. 20 from 10 a.m. to 5 p.m. at 875 N. Michigan Ave.

  • Englewood Jazz Festival: The Englewood Jazz Festival kicks off in Hamilton Park tonight for its 27th year, bringing three days of original music to Chicago’s South Side. This year’s free festival celebrates emerging creative musicians alongside centennial tributes to jazz legends Oscar Brown Jr., John Coltrane and Miles Davis. Performances take place indoors Thursday and Friday, with the festival moving outdoors Saturday, rain or shine.

  • World Dumpling Fest: 10+ Chicago-area restaurants will serve up dumplings from cultures around the world at the sixth annual World Dumpling Fest this weekend. The festival moves to a new home in Lincoln Park this year, featuring food, live music, dance and local small businesses. The event supports the Chicago Cultural Alliance and takes place in Wrightwood Park at 2555 N. Ashland Ave. Saturday, Sept. 19 from 11 a.m. to 10 p.m. and Sunday from 11 a.m. to 8 p.m.

Poll Question of the Week

With the Chicago River Swim happening this weekend, would you ever swim in the Chicago River?

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Last Newsletter's Poll Results

Poll Results: Last week, we asked if you think the Chicago Bears will win the NFC North this season, and 75% of you said yes.

Sunrise & Sunset in Chicago

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

  • Sunrise: 6:32 a.m. (7 minutes later)

  • Sunset: 6:56 p.m. (12 minutes earlier)

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