Chicago is the Best Big City

BEST DATE NEWS

Oct. 9, 2025: Best Date News Volume #147

Welcome to Best Date News, your favorite Chicago weekly newsletter! In this week’s edition, you’ll read about Chicago being named the Best Big City in the U.S., the 2025 Chicago Marathon, Chicago sports, new restaurant and store openings, weekend plans and more!

Oct. 9: National Holidays

• International Beer and Pizza Day

• National Depression Screening Day

• National Moldy Cheese Day

• Leif Erikson Day

• World Sight Day

Sponsored by our friends at Travel Wisconsin

Plan Your Fall Wisconsin Getaway

• Travel Wisconsin: Here’s to trading skylines for tree lines this fall. Just a short drive from Chicago, Wisconsin comes alive each October with cozy cabins, colorful trails and small towns that look straight out of a postcard. It’s one of the best places in the country to experience fall colors at their peak.

• It’s a once-a-year spectacle so stunning that Travel Wisconsin built an entire Wisconsin Fall Color Report for it. Use it to plan your getaway around the best views at the perfect time. It keeps the latest updates right at your fingertips.

• Whether your perfect autumn day means road tripping through state parks, hiking crimson forests, visiting apple orchards and craft breweries or sipping cider with cheese curds by the lake, there is a way for everyone to chase peak color in Wisconsin.

• The time is now to plan your fall Wisconsin getaway. Don’t miss the chance to see how Wisconsin puts the awe in autumn.

Chicago News

• Best Big City: Chicago was just named the “Best Big City in the U.S.” by Condé Nast Traveler for a record-breaking ninth year in a row. The title comes from the magazine’s 2025 Readers’ Choice Awards which drew votes from more than 750,000 participants. Rounding out the top five were San Francisco, Milwaukee, Portland and New Orleans.

• Chicago Marathon: Do you know any of the 53,000+ runners taking on the Chicago Marathon this Sunday, Oct. 12? The 47th annual race covers 26.2 miles through 29 neighborhoods, beginning and ending in Grant Park with nearly 2 million spectators expected along the route. Streets across the course will be closed from 6 a.m. to 4 p.m., so the best way to get downtown is by train. You can track runners through the Bank of America ChiMarathon app or watch live coverage on NBC 5 Chicago and Telemundo Chicago from 7 to 11 a.m. Here’s a guide of where to eat along the route.

• Chicago Cubs: For the second straight Thursday, the Cubs are facing a win or go home game to keep their season alive. Game 4 of the NLDS against the Milwaukee Brewers begins tonight at 8:08 p.m. at Wrigley Field. If the Cubs win, they’ll force a decisive Game 5 in Milwaukee on Saturday, Oct. 11 at 3:38 p.m. If they lose, the season ends. So you’re saying there’s a chance!

• New Chicago Stores: A new two-floor Kith Chicago just opened this week in Gold Coast at 54 E Walton Street, complete with a Kith Treats on the second floor. The second U.S. Jellycat shop opened inside Nordstrom at The Shops at North Bridge on Michigan Ave, and shoppers lined up early to get their hands on the plush toys. Luxury California supermarket Erewhon, famous for its high-priced goods, announced plans to open new stores in 20 U.S. cities with Chicago on the list.

• Chicago Blackhawks: With the Cubs battling it out in the MLB Playoffs, you may have missed that the NHL season officially kicked off this week. The Chicago Blackhawks opened with a tough loss to the defending champion Florida Panthers on Tuesday during their banner-raising night. They’re back in action tonight in Boston and will play their first home game this Saturday, Oct. 11 at 6 p.m. against the Montreal Canadiens.

Just For Fun

• Crying Tiger: One of River North’s most highly anticipated restaurant openings is set to arrive within the next week, with an official announcement expected any moment. From Lettuce Entertain You and acclaimed chef Thai Dang of HaiSous, Crying Tiger will open at 51 W Hubbard St with a menu inspired by flavors from across Southeast Asia. The restaurant takes over most of the former Hub 51 space, which closed last June and was reimagined into this concept and the already open Gus’ Sip & Dip.

• Bar Tutto: West Loop is getting another new restaurant from Joe Flamm’s Day Off Group this winter. Bar Tutto is set to open in December inside the new Flora Tower at 1110 W Carroll Ave, joining the group’s other neighborhood spots Rose Mary, BLVD Steakhouse and il Carciofo. Described as an “all-day Italian escape,” it will be the group’s first restaurant designed to serve breakfast, lunch and dinner.

• The Lion King: The Broadway sensation and Disney classic The Lion King has officially returned to Chicago, now running at the Cadillac Palace Theatre in the Loop through Oct. 19. The award-winning production features its iconic costumes, choreography and soundtrack, bringing Simba’s journey to life on stage. For those hoping to score affordable seats, Broadway in Chicago is hosting a daily drawing for $30 tickets, and Metra is offering free rides for riders heading to the show.

• Pumpkin Patches: With it already being the second week of October, it’s officially time to visit a pumpkin patch or two and soak in all the fall vibes Chicago has to offer. We put together a list of our top 10 pumpkin patches across Chicagoland, plus 22 more in the caption for you to explore. Did your favorite make the cut?

• Titanic Live in Concert: Titanic is coming back to the big screen in a way you’ve never seen before. The Chicago Philharmonic will perform James Horner’s iconic score for Titanic Live in Concert at the Auditorium Theatre on Friday, Feb. 13, led by conductor Emil de Cou with appearances from original soundtrack soloist Eric Rigler and Uniting Voices Chicago. Tickets go on sale tomorrow, Friday, Oct. 10 at 10 a.m.

Sponsored by our friends at Dearly Beloved

Omakocktail at Dearly Beloved

• Dearly Beloved: One of Chicago’s most imaginative cocktail destinations, Dearly Beloved, invites you to experience Omakocktail, a first of its kind cocktail omakase where nine carefully curated courses meet craft cocktail artistry.

• Hosted monthly, this intimate tasting experience guides guests through a progression of inventive, seasonal 2 oz cocktails, each thoughtfully paired with a small bite. Every dish and drink are designed to complement one another, creating an evening of unexpected flavors and culinary balance.

• The chefs rotate for each Omakocktail experience, bringing new energy and perspective to the menu. The visiting chef for this month’s experience is Won Kim of Kimski and Lilac Tiger, known for his bold flavors and creative approach to modern Korean cuisine.

• The next Omakocktail experience takes place Tuesday, Oct. 28, with two seatings from 6 to 8 p.m. and 8:30 to 10:30 p.m., limited to 20 guests each. Tickets are $130 per person for the prix fixe experience.

Weekend Plans

• Chicago Fashion Week: Kicking off today, the second edition of Chicago Fashion Week shines a spotlight on local designers and creatives through Oct. 19 with more than 60 runway shows, markets, social events, exhibits and networking opportunities across the city and suburbs. Events span neighborhoods from Hyde Park to Highland Park, with most free and open to the public. View the full 2025 schedule of events.

• Oktoberfestiversary: Begyle Brewing and Dovetail Brewery are hosting their 10th annual Oktoberfestiversary this weekend in Ravenswood at Begyle Brewing (1800 W Cuyler Ave). The two-day celebration runs Saturday, Oct. 11 from 11 a.m. to 9 p.m. and Sunday, Oct. 12 from 11 a.m. to 8 p.m., featuring food trucks, live music, family-friendly activities and plenty of beer. Performers include the Wiggleworms from Old Town School of Folk Music, Tuba Force, DJ Bloodshot Scott and more. Admission is free, with a $5 suggested donation supporting The Friendship Center food pantry.

• Lincoln Brunch Fest: Brunch lovers, this one’s for you. Lincoln Brunch Fest returns for its second year this Saturday, Oct. 11 from 10 a.m. to 2 p.m., taking over Lincoln Avenue from Diversey to Wellington in Lakeview. The street fest says it will feature brunch bites from top local restaurants, live entertainment and kid-friendly activities.

• The Lazy Run: Chicago’s shortest race is back this Saturday, Oct. 11 at 11 a.m. starting from Lottie’s Pub at 1925 W Cortland St. The Lazy Run 0.5K takes participants on a 0.31-mile loop from the bar to the park and back, kicking off with a Heineken shotgun start and featuring hydration stations of doughnuts and hot drinks along the way. Each registration includes a slice of Lottie’s pizza plus prizes for best costume and best spirit.

• The Goodman Costume Sale: Step inside the Goodman Theatre’s Healy Rehearsal Room this Saturday, Oct. 11 from 10 a.m. to 4 p.m. for a one-day Costume Shop Sale featuring pieces from decades of iconic productions. From whimsical accessories to show-stopping gowns, each item was handcrafted by the Goodman’s costume artists and ranges from $0.50 to $300. Credit cards only, all sales final.

Poll Question of the Week

Last Newsletter's Poll Results

Poll Results: Last week we asked if October is one of your favorite months of the year, and an incredible 80% of you said yes. Here’s one of the responses a reader sent in about why they love October:

• “It’s the best month because the weather is getting a bit crisp, but it isn’t cold. The trees are at color-changing peak, there are a lot of festivals and festivities, and all things pumpkin themed are fantastic.”

Sunrise & Sunset in Chicago

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

• Sunrise: 6:56 a.m. (8 minutes later)

• Sunset: 6:18 p.m. (11 minutes earlier)

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