Welcome to September, Chicago

BEST DATE NEWS

Sept. 4, 2025: Best Date News Volume #142

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about the Taste of Chicago, two new dessert shops opening in Chicago, Beef & Liberty, the Chicago Bears, weekend street festivals and more!

Sept. 4: National Holidays

• National Wildlife Day

• National Macadamia Nut Day

• National Eat an Extra Dessert Day

• National Newspaper Carrier Day

• National Spice Blend Day

Sponsored by our friends at Hubbard Haus

Chicago’s #1 Oktoberfest

• Hubbard Haus: A one-day Oktoberfest experience is coming to the heart of River North’s premier party street for the ultimate German block party. It’s called Hubbard Haus, and it will be a street-wide celebration of beer, food, music and more, featuring some of Hubbard Street’s most popular venues.

• 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, with an additional seven floors of festive bar fun to enjoy. There will be steins, pretzels, bratwurst, nonstop music indoors and out and outdoor beer specials. It will make for the largest outdoor college gameday football watch party in Chicago!

• During this Chicago-style Oktoberfest event, you can expect a German-style beer hall tent, both authentic German oompah bands during the day and Chicago’s top DJs and house music at night. It’s the perfect way for young professionals in Chicago to experience real German tradition with the added layer of Chicago’s party expertise.

• 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, all part of year one of this unvergesslich celebration. Don’t miss the all-access ticket with four drinks included!

Chicago News

• Taste of Chicago: Chicago’s biggest food festival returns to Grant Park Friday through Sunday, Sept. 5–7, from 11 a.m. to 9 p.m. Taste of Chicago will feature 60 local vendors alongside two live music stages with headliner performances from Lupe Fiasco, JoJo and Elvis Crespo, plus dance lessons, karaoke, neighborhood trivia and more. New this year, Taste of Chicago will close out Saturday, Sept. 6, with an 8:15 p.m. drone show set to music followed by fireworks over the lakefront. Note that only credit cards are accepted by food vendors and no food tickets will be sold.

• Van Leeuwen: Van Leeuwen Ice Cream, the cult-favorite brand from New York City, is opening its first Chicago shop in Wicker Park on Sept. 12 at the Six Corners intersection. The shop will serve more than 30 flavors, from Honeycomb and Earl Grey Tea to Sicilian Pistachio, along with vegan options. To celebrate, Van Leeuwen is launching a Chicago-exclusive Malört ice cream with Jeppson’s, plus $1 scoops from 11 a.m.–1 p.m. and free totes for the first 100 guests. A second location is set to open at Willis Tower later this fall.

• Beef & Liberty: Hawksmoor Chicago is opening its swanky, new London-style cocktail den, Beef & Liberty, on Sept. 19. Located on the second floor of Hawksmoor, the 40-seat lounge will serve cocktails like the Park Lane Cosmo and Sour Cherry Negroni, plus British bites such as scotch eggs and sausage rolls. The bar will also keep things fresh with pop ups from world class bars flying in from London, with big names set to take over throughout 2026.

• The Cookie Bar: The Cookie Bar by Summer House opened yesterday, Wednesday, Sept. 3, in Streeterville at 161 E Huron. The famous cookies from Lettuce Entertain You’s Summer House Santa Monica now have their own Chicago shop, paired with La Colombe cold coffee. Expect soft serve with mix ins and floats that bring summer vibes year round. It is the brand’s first standalone concept.

• Sundays on State: The award winning block party Sundays on State returns to State Street this weekend on Sunday, Sept. 7 and again on Sunday, Oct. 5, from 11 a.m.–6 p.m. The stretch from Randolph to Jackson will close to cars and fill with art, culture, food, drinks, shopping and performances in the heart of the Loop. It’s free to attend, leashed, well-behaved dogs are allowed and you can bring outside food and non-alcoholic beverages.

Just For Fun

• NFL Kicks Off: Are you ready for some football? The NFL season kicks off tonight with the Dallas Cowboys facing the defending Super Bowl champion Philadelphia Eagles at 7:20 p.m. The Chicago Bears will make their season debut in the national spotlight on Monday Night Football, hosting the Minnesota Vikings at Soldier Field on Sept. 8 with kickoff at 7:15 p.m.

• Macy’s Walnut Room: Chicago’s iconic Walnut Room is giving diners first dibs on coveted holiday reservations as part of its 118th anniversary celebration. Guests who dine in through Sept. 23 will get early access to book their holiday spot before reservations open to the public on Sept. 25.

• Ariana Grande: Pop star Ariana Grande is bringing her Eternal Sunshine Tour to United Center on Aug. 3 and 5, 2026. You can sign up now through Sept. 7 to join the Artist Presale that starts on Tuesday, Sept. 9. General tickets will be available starting Sept. 10 at 10 a.m.

• LUXBAR Turns 20: The Gold Coast restaurant LUXBAR is celebrating their 20th anniversary with special $20 meal deal combos for all of September. For just $20, you can select either the Lux Royale (burger) or Buffalo Chicken Salad to go with a Moscow Mule or Old Fashioned.

• Magnolia Bakery: Pumpkin spice season has arrived, and Magnolia Bakery is celebrating with a limited-time pumpkin flavor of their famous banana pudding. It’s a pumpkin pudding layered with vanilla wafers and cookie butter. The fall favorite is available in store now through Oct. 12.

• September Concerts: Chicago has quite the lineup of concerts taking place at the United Center this month with names like Dua Lipa, Lady Gaga, Kali Uchis and more. See the full September lineup of who is taking over the UC.

Weekend Plans

• Retro on Roscoe: Roscoe Village’s biggest street fest Retro on Roscoe is back Sept. 5–7 with three stages of live music, the city’s top antique and classic car show, a kids zone, local eats, unique vendors and even a visit from the actual Wienermobile. They are also debuting a new VIP Experience and Wine & Spirits Tasting this year adding to the weekend fun. Hours are Friday 5–10 p.m., Saturday noon–10 p.m. and Sunday noon–8 p.m.

• Oktoberfest: The Chicago German-American Oktoberfest takes over Lincoln Square from Sept. 5–7 at 4521 N Lincoln Ave. Admission is free, with German hospitality in two tents, hearty food, beer and wine each day, and live music from four bands. The Saturday parade begins at 2 p.m. and runs along Lincoln Ave from Irving Park Rd to Sunnyside Ave. Hours are Friday 5–10 p.m. and Saturday and Sunday noon–10 p.m.

• Edgewater Music Fest: The inaugural Edgewater Music Fest brings 30+ music acts across two stages along with 80 vendors, local food and drinks, a kids zone and strong community vibes. The free fest, with a suggested $10 donation, takes over Broadway between Thorndale and Ardmore Friday through Sunday, Sept. 5–7. It marks the return of a top notch street festival to Broadway for the first time since 2019. Music runs from 5 p.m. Friday and from noon to 10 p.m. on Saturday and Sunday.

• Printers Row Lit Fest: Printers Row in South Loop turns into a book lover’s paradise this Saturday and Sunday, Sept. 6–7, from 10 a.m. to 6 p.m. Printers Row Lit Fest is celebrating 40 years with author talks, readings, panels and book vendors spread across six stages. The free fest stretches along South Dearborn from Ida B Wells to Polk.

• Renegade Craft: The flagship Wicker Park Renegade Craft Fair takes over Division Street between Damen and Ashland this Saturday and Sunday, Sept. 6–7, from 11 a.m. to 7 p.m. The fall season kickoff features more than 400 artists selling ceramics, jewelry, artisanal food, screen printed goods and more, plus local eats and drinks.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked if you were excited for Chicago to change seasons soon and it was almost perfectly split. 51% of you said yes, bring on fall, while 49% of you don’t want summer to end!

Sunrise & Sunset in Chicago

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

• Sunrise: 6:19 a.m. (8 minutes later)

• Sunset: 7:18 p.m. (11 minutes earlier)

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