It's Lollapalooza Weekend, Chicago

BEST DATE NEWS

July 31, 2025: Best Date News Volume #137

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about Lollapalooza 2025, the Chicago Cubs, Meet Me on Milwaukee, Scream Club, weekend plans and more!

July 31: National Holidays

• National Avocado Day

• National Chili Dog Day

• National Intern Day

• National Lifeguard Appreciation Day

• National Raspberry Cake Day

Sponsored by our friends at Union Sushi

Affordable Omakase in Chicago

• Union Sushi: River North’s Union Sushi has two of the most affordable omakase experiences in Chicago. They have a 5-course Hand Roll Omakase for $40 and a 10-course Premium Omakase for $99. You can also add on a $20 curated sake flight or a $40 wine pairing.

• Led by Chef Toshi from Sasebo, Japan, each experience is a curated journey through Japanese flavors through the use of high-quality ingredients.

• We did the 10-course experience, and it was fantastic! While the exact lineup is subject to change based on what is most fresh when you visit, you can expect Japanese A5 Wagyu, Hokkaido Uni, Caviar, Otoro and more.

• This experience is intimate, yet casual, and a great way to try out omakase at an affordable price. Seatings are limited and available Thursday through Saturday, so make a reservation soon.

Chicago News

• Lollapalooza: Today kicks off Lollapalooza, Chicago’s largest music festival, with four days of performances in Grant Park from July 31 through Aug. 3. The weekend is packed with top artists, plus plenty of Official Aftershows with last‑minute tickets still available. If you didn’t score a wristband, limited verified resale tickets remain, or you can catch the festival live on Hulu.

• Chicago Cubs: It has been a week of mixed emotions for Cubs fans. Hall of Famer and Chicago legend Ryne Sandberg passed away at age 65 after a battle with cancer, and the team will honor him with a ceremonial uniform patch. Meanwhile, MLB is expected to name Wrigley Field the host of the 2027 All‑Star Game, Tom Brady is opening his sports trading card and memorabilia store, CardVault by Tom Brady, tomorrow just outside the ballpark and PCA made some kids’ day with a surprise stop at their lemonade stand in Wrigleyville.

• Meet Me on Milwaukee: Wicker Park is going car‑free on a half‑mile stretch of Milwaukee Ave between N Damen and Ashland on the last Sundays of August, September and October. From 10 am to 5 pm, the street will be open to bikers and walkers, with live music, sidewalk sales and outdoor dining. The new series, called Meet Me on Milwaukee, could return next year if this three‑event test goes well.

• Scream Club: Have you heard about Chicago’s newest social club? Every Sunday evening at North Avenue Beach, Scream Club gathers to scream together and release stress. Founded by men’s coach and breathwork practitioner Manny Hernandez, the group offers a judgment‑free space to express emotions. Before the collective scream, participants write down something they want to let go of and toss it into the lake. Take a look.

• Air and Water Show: It’s almost that time of the year again, Chicago! The Chicago Air and Water Show will return Aug. 16 and 17 on Lake Michigan, and this year’s list of performers was just released. The U.S. Air Force Thunderbirds will headline, taking over from last year’s Blue Angels.

Just For Fun

• August Events: August is almost here, and some of the best events of the entire year are taking place this month. From the Chicago Air and Water Show to the Ducky Derby, these are seven of the biggest happenings to mark on your calendar.

• World’s Best Bar: Chicago is now home to the best bar in the world according to the 19th annual Spirited Awards that recently took place in New Orleans. The bar? Kumiko, the West Loop Japanese Dining Bar that serves up Japanese fusion cocktails, food and cocktail omakase experiences.

• Original Pancake House: The beloved Chicago legend, The Original Pancake House, is opening a new West Loop location on Monday, Aug. 4. Known for their signature pancakes, including their Dutch Baby, and generous portions, this West Loop location will mark their 6th Chicagoland spot.

• Aperol Spritz Day: Friday, Aug. 1 is National Aperol Spritz Day, and Electric Shuffle in River North is celebrating with $5 Aperol Spritzes all day long. You can have it served either on the rocks or frozen.

• Reese’s x Oreo: This might be the snack collaboration of the year as America’s number one candy and cookie are teaming up! Oreo and Reese’s are joining forces to create both a Reese’s Oreo Cup and an Oreo Reese’s Cookie. Fans are going nuts on social media. Here’s what they will look like.

Weekend Plans

• Lollapalooza Parties: Don’t have Lolla tickets this weekend? No problem! There are tons of afterparties, shows and events happening around the city after the festival gates close. Here’s a complete list of all the events broken down by day, time, location and performer.

• Fiesta Del Sol: Pilsen’s Fiesta Del Sol is back this weekend for its 53rd year. From July 31 through Aug. 3, you can enjoy carnival rides, live music, cultural art exhibits and plenty of delicious local and regional food. Admission is free, but if you want unlimited ride access, there’s an $85 four‑day Megapass available.

• Jeff Fest: The 24th annual Jeff Fest takes over Jefferson Memorial Park on Friday, Aug. 1 and Saturday, Aug. 2. The neighborhood tradition features live music, local food, arts and crafts vendors, a Kids’ Zone and a Community Stage with local talent. Tickets are $6.25 Friday and $11.50 Saturday, making it an affordable way to enjoy the weekend in Jefferson Park.

• Taste of Andersonville: The Taste of Andersonville is actually not until next Wednesday, Aug. 6, but we wanted to make sure you knew about it! The three-hour event lets you taste your way through sample plates at local restaurants. There are two different ticket options, the Nibble Route or the Nosh Route. If you buy tickets before Aug. 4, you can do one route for $40 or both for $75.

• Chicago Nostalgia: Looking to stay in this weekend and avoid the crowds? Take a moment to reminisce about the past. Block Club asked Chicagoans which closed restaurants they would most want to bring back, highlighting 16 beloved spots that are gone but not forgotten.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter, we asked you which Chicago trains you ride consistently. 62% said CTA, 15% said Metra, 4% both and 19% said neither.

Sunrise & Sunset in Chicago

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

• Sunrise: 5:43 a.m. (7 minutes later)

• Sunset: 8:09 p.m. (7 minutes earlier)

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