Chicago Closes Out September

BEST DATE NEWS

Sept. 25, 2025: Best Date News Volume #145

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about the Chicago Bears, Portillo’s CEO, upcoming events at Wrigley Field, our $1,000 Lettuce Entertain You gift card giveaway, weekend plans and more!

Sept. 25: National Holidays

• National Quesadilla Day

• National Lobster Day

• National Daughter’s Day

• National One-Hit Wonder Day

• National Comic Book Day

Sponsored by our friends at the Maine Lobster Marketing Collaborative

Happy National Lobster Day

• Maine Lobster: Happy National Lobster Day, Chicago! Our friends at the Maine Lobster Marketing Collaborative want you to celebrate by enjoying lobster today, whether at home or at one of your favorite restaurants.

• Looking for inspiration? We put together a guide to 10 Chicago spots serving Maine Lobster dishes. One highlight is Hugo’s Frog Bar in Gold Coast, where you can try their Lobster Cobb salad (pictured above) or their Lobster Roll stacked high on a Hawaiian roll. We loved both dishes!

• Maine Lobster is the sweetest, most tender lobster on earth. It is available year-round, but peak season runs from July through November, which means right now is the best time to indulge.

• Craving lobster at home? You can get it delivered directly to your door. Check out this list of trusted suppliers who ship fresh Maine Lobster nationwide.

Chicago News

• Chicago Bears: New renderings have been revealed of what the Chicago Bears’ proposed Arlington Heights stadium could look like, with architecture firm MANICA appearing to now be the lead design firm. The plans show a full entertainment district, including more tailgating space and a dedicated Metra stop near the venue. Meanwhile, the NFL’s finance committee approved the internal sale of a 2.35% stake in the team from the estate of Andrew McKenna, a record deal that values the Bears at a league-high $8.9 billion and raises the McCaskey family’s ownership to 77%.

• Portillo’s CEO: There was a big shake up at Portillo’s this week as Michael Osanloo, who has led the Chicago hot dog chain since 2018, resigned as CEO effective immediately. The company’s chairman has stepped in for now while Osanloo stays on briefly as an advisor, and a search is underway for the next permanent CEO. Portillo’s recently announced changes to its growth strategy, which included ending a Chicago breakfast pilot program, and today the chain has 90 restaurants across 10 states.

• Cubs Playoff Tickets: Single game tickets for a potential National League Wild Card round at Wrigley Field went on sale this morning at 10 a.m., and a limited number still remain. The best of three series would take place Sept. 30, Oct. 1 and Oct. 2. If the Cubs qualify it would mark their first postseason games with fans at Wrigley Field since 2018. You can also sign up for their “Fly the W” presale opportunity for a chance to purchase additional potential 2025 postseason games at Wrigley Field.

• John Mulaney: Speaking of Wrigley Field, for the first time in the ballpark’s history, a comedian will headline the historic venue. John Mulaney popped into the broadcast booth of the Cubs game on Tuesday to break the news that he will be headlining a show at Wrigley Field on July 11, 2026 as part of his Mister Whatever tour. Pre-sale registration is now open.

• Restaurant Openings: Eater Chicago just rounded up seven new Chicago spots to know this month. Highlights include Adalina Prime, a splashy Italian steakhouse in Fulton Market, Honey Butter Beach Club inside SPF Chicago in Lincoln Park and Atsumeru, a Nordic Japanese tasting menu in West Town. The list also features Puerto Rican–inspired smash burgers, South Chicago’s first ramen shop and Malört ice cream in Wicker Park.

Just For Fun

• Gift Card Giveaway: One of our biggest giveaways of the year is happening right now! We have teamed up with Smart City Locating to give away a $1,000 Lettuce Entertain You gift card, which has restaurants like Aba, Ema, Miru, Pizzeria Portofino, RPM Seafood, Sushi San, Tre Dita and so many more! Don’t miss out on your chance to win! Go enter the giveaway now!

• The Wiener’s Circle: Remember how The Wiener’s Circle promised to give away free hot dogs if Caleb Williams threw four touchdowns last weekend? Well it happened, and it was quite the scene! Surprise special guests included Caleb’s dog Supa and Chicago Bears’ mascot Staley Da Bear.

• Coolest Neighborhoods: Chicago’s Avondale neighborhood just landed at number five on Time Out’s list of the 39 coolest neighborhoods in the world, released yesterday. The ranking spotlights culture, community, food and nightlife, praising Avondale’s mix of industrial grit and new restaurants. Logan Square came in at number 34 last year, but this time Avondale takes the spotlight. Curious who else is on the list? See the rankings.

• Meet Me on Milwaukee: The second Meet Me on Milwaukee takes place this Sunday, Sept. 28, with Milwaukee Avenue in Wicker Park closed to cars from the North/Damen intersection to Ashland. From 10 a.m. to 5 p.m. the street transforms into a pedestrian-only space with live music, shopping, biking and plenty of room to hang out.

• Navy Pier Open Air: Carl Cox takes the stage at Navy Pier this Friday, Sept. 26, closing out the 2025 Navy Pier Open Air season with a rare Chicago appearance. Known for his legendary Ibiza sets and explosive energy, the dance music icon will headline alongside John Digweed, Archie Hamilton b2b Sidney Charles and Muffy. Ages 18+ are welcome, with doors opening at 4 p.m. Get tickets here.

Sponsored by our friends at EXP

EXP Opens Tomorrow in Rosemont

• EXP Rosemont: Chicagoland’s newest destination for immersive entertainment opens tomorrow, Friday, Sept. 26 at 9900 Berwyn Avenue in Rosemont’s Pearl District. EXP Rosemont is the Midwest’s newest and largest permanent virtual reality space at 26,000 square feet, featuring free-roaming adventures that rotate every few months for groups, families and friends.

• Tickets start at $27 for children and $39 for adults. Use our discount code BESTDATE to get 20% off each ticket (excluding VIP and bundles). Discount valid on tickets for experiences from Sept. 28 to Oct. 26.

• Guests can choose from two 45-minute expeditions. Horizon of Khufu takes you back 4,500 years to ancient Egypt, where you can sail the Nile and step inside the Great Pyramid. Life Chronicles spans 3.5 billion years of evolution, letting you explore prehistoric forests and encounter life-sized dinosaurs and giant marine reptiles.

• The experience is designed for guests ages 8+, making it a fit for families, friend groups and anyone looking for something new to do in Chicagoland. Free-roaming technology makes every adventure feel real, and with new storylines rotating in regularly there is always a reason to come back.

Weekend Plans

• All You Can Eataly SeptemberFest: One of Eataly’s best and biggest events of the year is happening this Friday, Sept. 26. All You Can Eataly SeptemberFest is an all-inclusive, four-hour party with unlimited food and drinks. There will be 40+ bites, 30+ wines, spirits, beer, entertainment, live music, chef demonstrations, bocce ball, games and more. The event is $119 per person (or $109 with coupon code BDF10) for 7:30 p.m. entry tickets. The 7 p.m. entrance slots sold out already, so act quickly!

• Hubbard Haus Oktoberfest: A one-day Oktoberfest experience is coming to the heart of River North this weekend. Hubbard Haus will take place on Saturday, Sept. 27 from 12–9 p.m. The street will be closed and transformed into a Bavarian block party, plus seven floors of festive bar fun. There will be steins, pretzels, bratwurst, nonstop music indoors and out and outdoor beer specials. Admission is open to the public with suggested donation day-of, or you can grab pre-sold ticket options (starting at just $10) for priority access, drink inclusions and festival entry.

• Chicago Gourmet: One of the top food festivals in the country takes place this weekend in Chicago! Chicago Gourmet is a four-day, food and drink festival that celebrates Chicago’s world-class culinary scene and brings together top chefs and restaurants for a series of signature events on the Harris Theater Rooftop Terrace at Millennium Park. Events run from Sept. 25–28 and include Tacos & Tequila, Hamburger Hop, Grand Cru, Asian Late Night Market, Somm Sessions and Rise & Shine Gourmet.

• Goose Island 312 Block Party: The Goose Island 312 Block Party is back Saturday, Sept. 27 outside the Goose Island Taproom. This annual end-of-summer celebration runs from 3–10 p.m. and is free to attend for ages 21+. Expect more than 50 beers for $5, food trucks, innovation brews from the Taproom and Salt Shed Pub, plus guest pours from Old Irving, Great Central and Midwest Coast. Live performances include American Football, Hinds, Sonido Gallo Negro and Local Memory.

• Hyde Park Jazz Festival: The 19th annual Hyde Park Jazz Festival returns Sept. 27–28 with an unforgettable weekend of free world-class jazz across Hyde Park. Venues include the DuSable Black History Museum, Hyde Park Union Church and the Midway Plaisance, with performances from Jason Moran, Trio Imagination and Fay Victor’s Herbie Nichols SUNG. The festival also marks milestones for the Association for the Advancement of Creative Musicians, the Asian American Jazz Festival and drummer Hamid Drake. A $10 donation per person is suggested.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked what you thought of The Summer I Turned Pretty finale. An overwhelming 80% of you were happy with how it ended!

Sunrise & Sunset in Chicago

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

• Sunrise: 6:41 a.m. (7 minutes later)

• Sunset: 6:41 p.m. (13 minutes earlier)

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