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BEST DATE NEWS

May 15, 2025: Best Date News Volume #126

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s newsletter you will read about Family Meal Monday, the Chicago Bears schedule release, summer temps, Pope Leo, The Bear and more!

May 15: National Holidays

• National Chocolate Chip Day

• National Bring Flowers to Someone Day

• National Asphalt Day

• National Nylon Stocking Day

• International Day of Families

Sponsored by our friends at RIU Plaza Chicago

The Rooftop Bar at RIU Plaza Chicago

• RIU Plaza Chicago: Just off Michigan Ave, RIU Plaza Chicago (150 E Ontario St) has an incredible 27th-floor rooftop with amazing views, affordable cocktails and a legit food menu with over 20 different items.

• The most iconic feature of The Rooftop is the suspended glass balcony. It’s clear and juts out 27 stories above the street. It’s only for the brave because you can see all the way down. Could you do it?!

• Cocktails start at just $14 (a steal especially considering the views) and include options like an Espresso Martini, Aperol Spritz, Cosmopolitan, Manhattan and Moscow Mule. For food, we highly recommend getting the Coconut Shrimp. See the food menu.

• Tonight and tomorrow are going to be in the 80s here in Chicago, which means rooftop season has arrived! Make a reservation now before they’re all gone.

Chicago News

• Family Meal Monday: The popular Family Meal Monday at Spilt Milk Tavern is officially back for 2025, and this year they’re partnering with Culinary Cares too. Family Meal Monday brings some of Chicago’s best chefs and restaurateurs to Spilt Milk’s patio on Monday nights throughout the summer. From 5 p.m. until sellout (and it will), you can get a plate of food and one drink for $25. This year’s lineup includes names like Kasama, Daisies, Le Bouchon, Galit, Taqueria Chingon, Noodlebird and many more.

• Chicago Bears: The NFL released its full 2025 season schedule last night. Every team now competes to drop the most creative social media video, and the Chicago Bears did a pretty solid job with theirs. For the first time this century, the Bears will open their season on Monday Night Football. They'll face the Minnesota Vikings at Soldier Field on Monday, Sept. 8. See their full schedule.

• Summer Temps: It’s warm today, like really warm! We’ll see summer-like temperatures in the 80s both today and tomorrow before things cool down starting Saturday. Combine this warmth with 8 p.m. sunsets officially being back for 89 straight days, and Summertime Chi vibes are starting to break through little by little. Need a good picnic spot? This one’s a favorite!

• Pope Leo: You were probably aware that the new Pope Leo XIV was from the Chicago area, but did you know that his childhood home in Dolton, Ill. was listed for sale when he was elected? As you can imagine, things changed dramatically the moment he was elected, and the home listing was removed. See how much it was listed for and what the seller’s plans are now in this article. You also have to watch this video that discusses the whole situation.

• Butch McGuire’s: It sounds like Butch McGuire’s may soon be opening a second location. According to Crain’s, the iconic Division Street bar just registered an LLC for a new two-story spot at 2249 N. Lincoln Ave in Lincoln Park. This planned expansion would be in addition to the current 63-year-old Gold Coast location, not replacing it.

Just For Fun

• The Bear: Now here is a group who would participate in Family Meal Monday! FX just dropped the release date for The Bear Season 4. It officially premieres June 25 on Hulu (and now also streams on Hulu via Disney+). Could this be the last season for the popular, Chicago-based TV show?! If it is, we are excited to see what’s in store.

• Concert Announcements: With the addition of country music star Jake Owen, the Illinois State Fair has now finalized its list of headliners for this summer’s event that includes names like Snoop Dogg and The Chainsmokers. Grammy-winning artist Kali Uchis just announced The Sincerely Tour in support of her new album. She will be performing in Chicago at the United Center on Sept. 23, her second to last tour stop. The next day, NBA YoungBoy will be bringing the MASA Tour to the United Center on Sept. 24.

• Old Orchard Mall: Puttshack is set to open its second Illinois location on June 18 at Westfield Old Orchard Mall in Skokie, Ill. The tech-infused miniature golf company will be opening in a massive 30,000-square-foot space that was previously home to department store Lord & Taylor in 2018. There will be four courses of nine holes each, two full-service bars and more.

• Por Osos: Comedians Tom Segura and Bert Kreischer are taking over Chicago with their vodka brand, Por Osos, on May 21. They’ll start with a $10 ticketed bottle signing at Binny’s from 2 to 4 p.m., then host a bar takeover at Old Crow Smokehouse in Wrigleyville at 8 p.m. The evening event is free and open to the public for those 21 and over.

• May Concerts: If you don’t want to wait until later this year to see a concert, this has to be one of the most stacked May concert lineups of all time in Chicago. Rauw Alejandro and Katy Perry both took the stage at the United Center this past week, and we still have upcoming May performances from Beyoncé, Post Malone, AC/DC and The Weeknd.

Weekend Plans

• Beyoncé: It’s Beyoncé weekend in Chicago! Queen Bey kicks off her three-show Cowboy Carter Tour stop tonight at Soldier Field, with performances on May 15, 17 and 18. If you’re going, here’s everything you need to know. If you’re not, here are Nine ways to celebrate Beyoncé in Chicago this week.

• Crosstown Classic: The Crosstown Classic is back this weekend as the Cubs and White Sox face off at Wrigley. It’s one of Chicago’s favorite summer traditions, whether or not you care about the rivalry! One thing is for sure, we know who Pope Leo will be rooting for.

• Weekend Plans: With festivals, concerts, sports and more, there is a lot happening in Chicago this weekend! For a full list of things you can do, check out this weekend guide from Choose Chicago.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last newsletter we asked which new frozen snack item you were more excited to try. 58% of you said Pop-Tarts Ice Cream Sandwiches and 42% of you said Cheez-It Frozen Pizzas.

Sunrise & Sunset in Chicago

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

• Sunrise: 5:31 a.m. (7 minutes earlier)

• Sunset: 8:03 p.m. (8 minutes later)

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