
BEST DATE NEWS
May 21, 2026: Best Date News Volume #179
Welcome to Best Date News, your go-to guide for what’s happening in Chicago! This week, we’re diving into the Taste of Chicago lineup, a new Marriott hotel coming to the former John Hancock Center, a naming contest for Chicago’s new eaglets, Memorial Day Weekend festivities and much more.

Via Chocolate with Grace
May 21: National Holidays
National Strawberries and Cream Day
National Talk Like Yoda Day
National Chardonnay Day
National Waitstaff Day
International Tea Day
Sponsored by our friends at Travel Wisconsin

Via Travel Wisconsin
Mark Your Calendars: Wisconsin’s Biggest Summer Events of 2026
Travel Wisconsin: Wisconsin has an incredible lineup of summer events this year, from huge music festivals and iconic fairs to one of the world’s biggest aviation showcases. Many of them are a short drive from Chicago, making for a perfect summer trip.
Music fans have plenty to look forward to this summer. Summerfest in Milwaukee brings more than 600 artists to the lakefront across three weekends, while Mile of Music takes over downtown Appleton with hundreds of performances across dozens of venues. Meanwhile, the beloved indie music and arts festival Eaux Claires is returning this summer after an eight-year hiatus.
The Wisconsin State Fair celebrates its 175th year with iconic fair food, rides, entertainment and its famous “Sporkies and Drinkies” food competition. Meanwhile, Madison’s Art Fair on the Square transforms the Capitol area into a massive outdoor art festival with hundreds of artists, food vendors and live entertainment. Aviation fans can also check out EAA AirVenture Oshkosh, one of the world’s biggest aviation showcases.
If you’re looking for a fun summer road trip from the Chicagoland area, Wisconsin has no shortage of events worth adding to your calendar this summer. Check out all the summer events happening across the state and start planning your trip now!

Via Patrick L. Pyszka, City of Chicago
Chicago News
Taste of Chicago: Taste of Chicago just announced its 2026 lineup of headliners this morning, with artists like Common, Beach Bunny, Babyface, Julieta Venegas and Original Koffee set to headline this summer’s festival. The free five-day event returns to Grant Park July 8–12 and moves back to its traditional midsummer timeframe after being held in September the last few years because of the NASCAR Chicago Street Race. See this year’s Taste lineup of 84 food vendors from across Chicago.
New Marriott Hotel: A new luxury Marriott hotel could be coming to the former John Hancock Center. Marriott is reportedly in advanced talks to bring its luxury Edition hotel brand to 875 N. Michigan Ave., where a proposed 350-room hotel would take over vacant office space on floors 23 through 34 of the tower. If finalized, this would become Chicago’s first Edition hotel and another major change for the building following the closure of the Signature Room. See what people are saying about it.
Lakefront Beaches: Chicago’s lakefront beach season officially begins tomorrow, giving residents access to the city’s 26 miles of open and free lakefront. City beaches open Friday, May 22, with daily swim hours running from 11 a.m. to 7 p.m. Memorial Day weekend through Labor Day. Officials are also reminding visitors to only swim when lifeguards are on duty and to check water conditions before heading to the beach.
Pokémon Fossil Museum: The Pokémon Fossil Museum exhibition officially opens this Friday at the Field Museum. The interactive exhibition is making its North American debut in Chicago and compares Fossil Pokémon to real prehistoric fossils and creatures. Visitors will be able to see fan-favorite Pokémon, fossil excavation tools, immersive soundscapes and comparisons between Pokémon like Tyrantrum and Archeops and real fossils like SUE the T. rex. The exhibition runs through April 11, 2027.
Zillow Dispute: Shopping for a home in the Chicago area? Thousands of Chicagoland home listings are disappearing from Zillow and Trulia after a major dispute between Zillow and Midwest Real Estate Data (MRED), the company that powers local real estate listings. MRED claims Zillow violated an agreement regarding how certain private listings are displayed, while Zillow says the rules changed after the deal was signed.

Via Chicago Park District
Just For Fun
Chicago Eaglets: Two bald eaglets recently hatched on the Southeast Side and are believed to be the first eagles born in Chicago in over 100 years. The Chicago Park District says the eaglets are about a month old and were discovered in a nest high in the cottonwood trees near a restored nature area. The Park District is now holding a “Name the Eaglets” public naming contest, with finalists including Migizi, Marian and Clawumet. Voting is open now through June 1.
Summer Fireworks: Chicago’s award-winning summer fireworks return to Navy Pier for the first time this season on Saturday, May 23. There will be more than 30 shows taking place this summer, with fireworks scheduled twice a week on Wednesdays at 9 p.m. and Saturdays at 10 p.m. through Labor Day weekend. See the full schedule.
Lincoln Park Zoo: Lincoln Park Zoo is hosting a free four-day Summer Kickoff celebration this Memorial Day weekend. The family-friendly event will feature special rides and attractions like a Ferris wheel, giant slide and mini race cars along with zoo programming and other activities throughout the weekend. The zoo is also hosting a 21+ Adults Night Out: Block Party tomorrow evening featuring mini golf, DJs, games and after-hours zoo access. Ride tickets and Adults Night Out tickets are sold separately.
John Summit: Naperville native and University of Illinois graduate John Summit just announced his new CTRL ESCAPE arena tour, which will kick off in Champaign. Chicago is also one of only two cities on the tour getting two different shows, including two nights at the United Center on Nov. 24 and 25 in addition to his Lollapalooza set this summer. Tickets go on sale May 29.
Buffalo Grove: Buffalo Grove was just ranked the No. 1 place to live in Illinois for 2026 and No. 15 nationally in U.S. News & World Report’s new rankings. The rankings considered factors like quality of life, housing, crime, cost of living and the job market. Two other popular Chicago suburbs also made the national top 50 at spots No. 32 and No. 46. Can you guess which ones?

Via Sueños Music Festival
Weekend Plans
Sueños: Sueños Music Festival returns to Grant Park this Saturday and Sunday for the festival’s fifth year. The massive Latin music festival has quickly become one of Chicago’s biggest summer music events, with this year’s lineup featuring artists like J Balvin, Kali Uchis and Fuerza Regida across multiple stages. The weekend will also include food vendors, activations and a festival marketplace. One-day tickets start at $189. See ticket options.
Belmont Sheffield Music Fest: The Belmont Sheffield Music Fest returns to Lakeview this Friday, May 22 through Sunday, May 24 for its 41st year. The Memorial Day weekend street festival celebrates the unofficial start of summer in the heart of Lakeview with live tribute bands, food and drinks, local vendors and community performances. The event takes place just steps from the Belmont CTA station and admission is free with a suggested donation.
Mayfestiversary: Begyle Brewing and Dovetail Brewery are hosting Mayfestiversary this Saturday, May 23 and Sunday, May 24. The spring celebration of beer, music, food and community in the Ravenswood Corridor will feature live music, food vendors and family activities while also celebrating Dovetail’s 10th anniversary. The event takes place between the neighboring breweries and is free to attend with a suggested $5 donation.
Memorial Day Parade: Chicago’s annual Memorial Day Parade returns downtown this Saturday, May 23. The day begins with a wreath-laying ceremony at Daley Plaza at 11 a.m., followed by the parade at noon on State Street from Lake Street to Van Buren Street. The event honors the men and women who made the ultimate sacrifice while serving in the U.S. Armed Forces.
Randolph Street Market: Randolph Street Market returns to the West Loop this Saturday, May 23 and Sunday, May 24 from 10 a.m. to 5 p.m. for its 23rd annual Garden Party Market. The indoor-outdoor shopping festival will feature more than 200 vintage, antique and artisan vendors along with live music, food vendors and entertainment throughout the weekend. General admission tickets are $14 online or $15 at the gate and are valid for both days.
Poll Question of the Week
Do you consider Memorial Day Weekend the start of summer?
Poll Results: Last week, we asked if you were a Star Wars fan, and it was pretty evenly split, with 53% of you saying no. The new film The Mandalorian and Grogu comes out in theaters tomorrow. You can also check out the limited-time Star Wars x MINISO pop-up now open at Woodfield Mall.
Sunrise & Sunset in Chicago
Here is today’s outlook in Chicago (compared to last week):
Sunrise: 5:24 a.m. (7 minutes earlier)
Sunset: 8:09 p.m. (6 minutes later)
Sponsor Best Date News!
Sponsored posts allow us to keep Best Date News free for our readers. If interested in becoming a sponsor, please reach out to [email protected].

