BEST DATE NEWS

Aug. 20, 2026: Best Date News Volume #192

Welcome to Best Date News, your go-to guide for what's happening in Chicago! This week, we're diving into an Illinois tollway rate hike, Barnes & Noble opening in the Loop, Gingie’s reopening, big concerts this weekend, the Jesse White Tumblers, weekend activities and much more.

Via National Day Calendar

Aug. 20: National Holidays

  • National Bacon Lovers Day

  • National Radio Day

  • National Hazy IPA Day

  • National Chocolate Pecan Pie Day

  • World Mosquito Day

Sponsored by our friends at PAWS Chicago

Via PAWS Chicago

PAWS Chicago 5K Walk/Run for Their Lives

  • PAWS Chicago: Chicago’s largest dog-friendly charity event returns to Montrose Harbor on Saturday, Aug. 29! Celebrating its 26th anniversary, the PAWS Chicago 5K Walk/Run for Their Lives brings together thousands of animal lovers for a morning of running, walking and plenty of dog-friendly fun, all while raising critical funds to help pets in need.

  • The event runs from 7:30 to 11 a.m., with the 5K run starting at 7:45 a.m. and the walk at 9 a.m. Beyond the 5K, attendees can check out a Doggy Oasis relaxation station, dog agility course, raffles, giveaways, entertainment, treats, sponsor activities and adoptable pets.

  • Adult advance registration is $45 through Wednesday, Aug. 26 at 11:30 p.m., while child registration is $20. All participants receive an event T-shirt, wristband and personal fundraising page to raise funds and earn prizes. Anyone who raises at least $250 also receives access to the Hero Hangout, featuring additional food and alcoholic beverages.

  • Whether you want to run, walk or simply spend the morning surrounded by dogs and fellow animal lovers, it’s all for a great cause. Register for the PAWS Chicago 5K Walk/Run for Their Lives and help support PAWS Chicago’s lifesaving work for pets in need.

Via PBS

Chicago News

  • Illinois Tollway: Illinois tolls are officially going up next year after the Illinois Tollway Board unanimously approved the largest toll rate increase in state history yesterday. Starting Jan. 1, passenger vehicles with I-Pass will pay an additional 45 cents per toll, while drivers without I-Pass will pay an additional 90 cents per toll and commercial vehicle rates will increase by 30%. Rates will also be adjusted every other year based on inflation, with the increases helping fund the Tollway's $26.5 billion, 15-year "Driving Connections" infrastructure program.

  • New White Sox Stadium: Plans for a potential new White Sox ballpark near The 78 could have a clearer path forward thanks to more than $600 million in federal funding awarded to Amtrak. The funding will help move Amtrak operations from a 47-acre property along the Chicago River to a new facility in Bridgeport, making the riverfront land available for redevelopment. A firm led by potential future White Sox owner Justin Ishbia is already under contract to buy the property and has explored putting a new Sox stadium there, directly across the river from The 78.

  • Barnes & Noble: Barnes & Noble officially returned to the Loop yesterday, drawing long lines for the opening of its new flagship bookstore at State and Randolph streets. The 20,000-square-foot store spans three floors inside the historic building that once housed a flagship Borders and more recently Old Navy. It's the fourth new Barnes & Noble to open in the Chicago area this year, joining locations in Hyde Park, Oak Park and Skokie.

  • Gingie Chicago: Highly anticipated River North restaurant Gingie is officially reopening Aug. 29, exactly five months after originally opening its doors. The restaurant from Chef Brian Lockwood, located at 707 N. Wells St., was forced to temporarily close following a minor kitchen fire shortly after its debut. Reservations just went live, and we expect tables to fill up quickly ahead of its return.

  • NASCAR Chicago Street Race: The NASCAR Chicago Street Race will officially remain on pause for another year, with NASCAR announcing it will not return to Grant Park in 2027. The downtown race was held from 2023–2025 before taking this year off, with hopes of returning next summer. Instead, NASCAR will once again race at Chicagoland Speedway in Joliet from June 25–27, although both NASCAR and the city have left the door open for the street race to return in 2028.

  • WNDR Museum: WNDR Museum is permanently closing its West Loop location next month after eight years in Chicago. Located at 1130 W. Monroe St., the museum is known for its interactive, Instagram-friendly installations and rotating exhibitions and has also hosted art classes, markets and other events over the years. Its final day will be Monday, Sept. 7.

Via America’s Got Talent

Just For Fun

  • Big Concert Weekend: It's a big weekend for concerts in and around Chicago. Jimmy Eat World will perform at Huntington Bank Pavilion tonight with The Get Up Kids and Sunny Day Real Estate at 7 p.m., while Ricky Martin makes his Ravinia debut at 8 p.m. with pre-concert salsa lessons starting at 6 p.m. Tomorrow, Kacey Musgraves brings her Middle of Nowhere Tour to the United Center with special guest Midland. Plus, the sold-out R&B Tour starring Usher and Chris Brown takes over Soldier Field Friday and Saturday.

  • Jesse White Tumblers: The Jesse White Tumblers' run on "America's Got Talent" came to an end last night after the Chicago-based group was eliminated in the quarterfinals. The team earned rave reviews from the judges for its live performance Tuesday but did not receive enough public votes to advance to the semifinals. The 92-year-old Jesse White says the Tumblers plan to return and compete again next season.

  • Dine Out on Broadway: Broadway will close to traffic between Belmont and Wellington this weekend for Dine Out on Broadway, giving Lakeview restaurants additional space to expand their outdoor patios into the street. The open-streets dining event runs Friday, Aug. 21 from 3 p.m. to 11 p.m., Saturday, Aug. 22 from 9 a.m. to 11 p.m. and Sunday, Aug. 23 from 9 a.m. to 10 p.m.

  • Chipotle BOGO: Chipotle is offering a buy-one-get-one-free entrée deal today for anyone who shows up wearing school colors, a school jersey or other school gear. The School Spirit BOGO is available in restaurants nationwide from 3 p.m. to close at participating locations.

  • Illinois Hallmark Town: One Illinois town has been named among 25 finalists for Hallmark's Merriest Christmas Town of 2026. The town was recognized for its historic square and holiday traditions, with public voting open through Sept. 4. The winning town could even become a filming location for a future Hallmark Christmas movie.

Sponsored by our friends at High Stakes Productions

Our Best Guest: An Improvised Mockcast Debuts Tonight

  • Our Best Guest: A new fully improvised mockumentary from Chicago’s High Stakes Productions debuts tonight! Inspired by movies like Best in Show and This Is Spinal Tap, Our Best Guest: An Improvised Mockcast turns an audience member’s real-life passion or community into an entirely original documentary-style comedy.

  • Each performance begins with a conversation with a special audience guest before a cast of improvisers dives into their world. Whether the inspiration is the National Cornhole Championships, competitive eating, historical reenactments or another niche obsession, the cast creates characters, rivalries, documentary interviews and a high-stakes event completely on the spot, meaning no two shows are ever the same.

  • The show is performed around live microphones with an onstage director guiding the story and a live Foley artist creating the world in real time. Each performance is also recorded in front of the audience and later released as a podcast.

  • There are three shows to catch at The Newport Theater, tonight through Saturday, Aug. 20–22 at 7 p.m. Tickets are just $15. Get your tickets for Our Best Guest: An Improvised Mockcast from High Stakes Productions!

Via Brian Cassella/Chicago Tribune

Weekend Plans

  • Lakeview Taco Fest: Tacos will take over the Southport Corridor this weekend for the 13th annual Lakeview Taco Fest, with Chicago restaurants serving up their best creations. The three-day festival also features two stages of live music, Lucha Libre wrestling, beer and taco pairings, family activities and a "Best Taco" competition. Friday, Aug. 21 from 4–10 p.m., Saturday, Aug. 22 from 11 a.m.–10 p.m. and Sunday, Aug. 23 from 11 a.m.–9 p.m. at 3500 N. Southport Ave. with a $10 suggested donation.

  • West Loop Art Fest: More than 100 artists and artisans will take over four blocks of Fulton Street this weekend for the annual West Loop Art Fest, featuring original artwork, ceramics, jewelry, fashion and handmade goods. The two-day event also includes interactive art, live demonstrations, street entertainment and the Bizarre Boutique with artisan goods and vintage finds. The free festival runs Saturday, Aug. 22 and Sunday, Aug. 23 from 10 a.m. to 7 p.m. on Fulton Street between Peoria and Aberdeen streets.

  • Supertri Chicago: A record 9,500 athletes will swim, bike and run through the city this weekend as Supertri Chicago, North America's largest triathlon, returns to Chicago. Spectators can watch the races along the lakefront and downtown as athletes make their way through Lake Michigan and past landmarks including Buckingham Fountain, Soldier Field and the Museum Campus. Saturday, Aug. 22 and Sunday, Aug. 23.

  • Chalk Howard Street: Howard Street will transform into a colorful canvas this weekend for Chalk Howard Street, Chicago's only 3D chalk art festival. The free, family-friendly event features internationally renowned 3D street artists, local chalk artists, live music, food and drinks, plus opportunities for attendees to create their own chalk art. Saturday, Aug. 22 from 11 a.m. to 7 p.m. on Howard Street between Paulina Street and Ashland Avenue in Rogers Park.

  • Chicago Bulls Fest: Chicago Bulls Fest returns to the United Center this weekend with a 3-on-3 tournament, Youth Hoops clinics, basketball competitions, Benny's Carnival and meet & greets with current and former Bulls including Caleb Wilson, Nate Robinson, Metta World Peace and Eddy Curry. Fans can attend Saturday, Aug. 22 and Sunday, Aug. 23 from 7 a.m.–5 p.m. for free, but a free ticket is required for entry.

Poll Question of the Week

In honor of National Bacon Lovers Day, are you a bacon lover?

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Last Newsletter's Poll Results

Poll Results: Last week, we asked if you were planning on watching the Chicago Air & Water Show, and the results couldn't have been any closer. The poll was split perfectly 50/50.

Sunrise & Sunset in Chicago

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

  • Sunrise: 6:03 a.m. (7 minutes later)

  • Sunset: 7:43 p.m. (10 minutes earlier)

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