BEST DATE NEWS

Oct. 8, 2026: Best Date News Volume #199

Welcome to Best Date News, your go-to guide for what's happening in Chicago! This week, we're diving into the Best Big City in the U.S., the Chicago White Sox, Chicago Marathon weekend, Chicago Fashion Week, weekend events and much more.

Via National Day Calendar

Oct. 8: National Holidays

  • National Pierogi Day

  • National Salmon Day

  • National Fluffernutter Day

  • National Touch Tag Day

  • World Octopus Day

Sponsored by our friends at Chicago Architecture Center

Via Chicago Architecture Center

Open House Chicago Returns Next Weekend

  • Chicago Architecture Center: Next weekend, Oct. 17 and 18, is Open House Chicago. The annual, one-weekend-only celebration gives you exclusive, behind-the-scenes access to 200+ sites across Chicago, including many that are not normally open to the public. The best part? It’s free!

  • With more than 200 sites to choose from, we recommend starting to plan your Open House Chicago weekend now. Browse the full list of sites, save your favorites, check out different itineraries and start mapping out which ones you want to visit. Make sure to double-check each site’s hours and which days they’re open since availability can vary throughout the weekend.

  • Some places are only open one day and popular sites can have long lines. Chicago Architecture Center members get a Priority Pass to skip the line at all 200+ sites. There are also talks, tours and special programs happening throughout the weekend that you can browse by neighborhood.

  • Here are our top 10 places to visit for Open House Chicago 2026:

    1. Uptown Theatre (Uptown)

    2. The Chicago Board of Trade Building (Loop)

    3. The Cliff Dwellers Club (Loop)

    4. Columbia Yacht Club (Lakefront)

    5. Avalon Regal Theater (South Shore)

    6. Federal Reserve Bank of Chicago and Money Museum (Loop)

    7. House of Blues (River North)

    8. Walt Disney House & Birthplace (Hermosa)

    9. Pui Tak Center (Chinatown)

    10. Broadway in Chicago’s Cadillac Palace Theatre (Loop)

Via Choose Chicago

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 10th consecutive year! The recognition comes from the magazine’s 2026 Readers’ Choice Awards, which received nearly 800,000 votes from travelers around the world. See which other cities made the top 10 Best Big Cities list (scroll down past the Best Small Cities list) and check out their rankings of the 10 best hotels in Chicago!

  • Chicago White Sox: The White Sox are just one win away from advancing to the American League Championship Series (ALCS). Leading the best-of-five series 2–1, they'll face the Cleveland Guardians tonight at 7 p.m. at Rate Field in another Blackout game, with fans encouraged to wear all black. We went yesterday, and the atmosphere was electric. A victory would mark the first time the White Sox have clinched a postseason series at home since 1906. Tickets currently start at $225+ on the secondary market.

  • Amazon: Your Amazon packages could soon be arriving even faster in Chicago. The company has purchased a massive, long-vacant warehouse at 1237 W Division St in West Town for $195 million, with plans to turn it into a same-day delivery center. The two-story, 590,000-square-foot facility near Goose Island will help Amazon deliver orders to Chicago customers in just a few hours rather than days. The facility is expected to open in late 2027 or early 2028.

  • Block 37: Chicago's Block 37 shopping mall in the Loop has been sold for $30 million to Edwards Realty Company, with plans to bring new life to the property. Located at 108 N State St, across from Macy's, the mall has struggled with vacant storefronts since opening in 2009. The new owners plan to maintain retail on the first two floors while introducing entertainment and interactive experiences on the largely vacant third floor.

  • IKEA: IKEA has announced plans to close its Bolingbrook location after more than 20 years and relocate to Naperville. The new store, expected to open in late 2027 at the Block 59 shopping center, will feature a smaller shopping format with a Swedish Food Market and Swedish Deli. The existing 310,000-square-foot Bolingbrook store will remain open until the new location is ready. IKEA also plans to open a smaller-format store at Gurnee Mills later this year.

Via PAWS Chicago

Just For Fun

  • Bears vs. Packers: The NFL's biggest rivalry returns this Sunday, Oct. 11, as the Bears (3–1) travel to Lambeau Field to face the Packers (2–2). Heads up, kickoff has been moved from 3:25 p.m. to noon CT, with the game airing on FOX. Just in time for the matchup, Foam Party Hats and PAWS Chicago have teamed up to create a pet-sized Graterhead hat, with a portion of proceeds benefiting PAWS. The hats will be available at the PAWS Lincoln Park Adoption Center this Friday, Oct. 9. Check out Caleb Williams' dog Supa modeling one.

  • Chicago Fashion Week: The third edition of Chicago Fashion Week kicks off today, shining a spotlight on local designers and creatives through Oct. 18 with dozens of runway shows, markets, social events, exhibits and networking opportunities across the city and suburbs. Events span locations from Hyde Park to Highland Park, with most free and open to the public. View the full 2026 schedule of events.

  • Pumpkin Patches: With October already in its second week, it’s officially time to visit a pumpkin patch or two and soak in all the fall vibes Chicagoland 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?

  • Portillo’s: Portillo’s has teamed up with OREO to launch three new limited-time desserts just in time for Halloween. The lineup includes an OREO Shake with crushed cookie pieces, an OREO Cake with cookie-filled white cake and OREO frosting and an OREO Cake Shake that blends the new cake into a vanilla shake. All three are now available nationwide.

  • Blank Street Coffee: Viral New York-based coffee chain Blank Street Coffee is coming to Chicago for the first time, with plans to open a 2,300-square-foot location at 1588 N Milwaukee Ave in Wicker Park. Known for its matcha drinks and specialty coffees, the rapidly growing chain will take over a former Starbucks space that closed last year. An opening date has not yet been announced.

  • Anthony Rizzo Run: Former Chicago Cubs star Anthony Rizzo is joining Brooks Running for a special 5K shakeout run this Saturday, Oct. 10, ahead of the Chicago Marathon. The free group run takes place at Brooks Hyperion House (401 N Michigan Ave) from 8:30–10 a.m., with the run starting at 9 a.m. Brooks Elite Athletes will also attend, with prizes, light bites and coffee afterward. RSVP is required.

Sponsored by our friends at Park Hyatt Chicago

Via Park Hyatt Chicago

An Immersive Two-Night Omakase is Coming to NoMI Kitchen

  • Park Hyatt Chicago: NoMI Kitchen on the seventh floor of Park Hyatt Chicago is completely transforming for HERITAGE SERIES: Japanese Artistry, an intimate omakase experience available for two nights only.

  • The experience brings together Japanese art, cuisine, whisky and vinyl with a Japanese tea welcome reception, six-course seasonal omakase and live gyotaku demonstrations by artist Dwight Hwang. Select seafood featured on the menu will be transformed into contemporary works of art using the traditional Japanese printmaking technique dating back to the mid-1800s.

  • Guests can also choose between a House of Suntory Whisky Pairing featuring rare pours unavailable to the public or a Non-Alcoholic Beverage Pairing. A live vinyl DJ inspired by Japan’s iconic listening bars rounds out the evening, and each guest will receive a hand-signed gyotaku print created during the event.

  • Japanese Artistry takes place Oct. 16 and 17 at 7 p.m. with only 18 seats each night. Limited tickets available. Learn more and get tickets.

Via Chicago Marathon

Weekend Plans

  • Chicago Marathon: Do you know any of the 55,000+ runners taking on the Chicago Marathon this Sunday, Oct. 11? The 48th annual race covers 26.2 miles through 29 neighborhoods, starting and finishing in Grant Park with 1.7 million spectators expected along the route. This guide has everything you need to know. Street closures will take place along the course from 6 a.m. to 4 p.m., so taking the train is your best bet for getting around. You can track runners through the Bank of America Chicago Marathon app or watch live coverage on NBC 5 Chicago and Telemundo Chicago starting at 7 a.m.

  • The Lazy Run: Not looking to run 26.2 miles this weekend? Chicago’s shortest race is back this Saturday, Oct. 10, at noon, starting at Lottie’s Pub. 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 “Shotgun Start” and featuring “Hydration Stations” with doughnuts and hot drinks along the way. Registration includes a slice of Lottie’s pizza, race day specials and prizes for best costume and best spirit.

  • Oktoberfestiversary: Begyle Brewing and Dovetail Brewery are hosting their 11th annual Oktoberfestiversary this weekend between the two breweries in the Ravenswood Corridor. The two-day street festival celebrates fall in Chicago with more than 50 beers, food trucks, live music and family-friendly activities. The festivities run Saturday, Oct. 10 from 11 a.m. to 9 p.m. and Sunday, Oct. 11 from 11 a.m. to 8 p.m. Admission is free, with a $5 suggested donation.

  • Bowmanville Cat Tour: The Bowmanville Cat Tour takes place this Saturday, Oct. 10, from 3–5 p.m. in Bowmanville, a neighborhood within Chicago's Lincoln Square community area. Explore the neighborhood and meet local cats, with plenty of cat-themed costumes expected from both pets and people. Visitors can follow the cat map at their own pace or join a guided tour starting at 3 p.m. or 4 p.m.

  • Lincoln Brunch Fest: Who doesn't love free brunch? Lincoln Brunch Fest returns for its third year this Saturday, Oct. 10, from 10 a.m. to 2 p.m., taking over Lincoln Avenue between Diversey and Wellington in Lakeview. Local restaurants and cafes will be serving up free samples of their brunch favorites, alongside live music, family-friendly activities, local business pop-ups and more. Both admission and food samples are completely free!

  • TenderFest: The world's largest all-you-can-eat chicken tender festival is coming to Chicago this Saturday, Oct. 10. Taking over Navy Pier, TenderFest brings together top chefs and restaurants serving up their best chicken tenders, creative recipes and signature sauces. Tickets include unlimited chicken tender tastings, while the festival also features cocktails, music, entertainment and a Joey Chestnut tender-eating competition. The festival runs from 11 a.m. to 3 p.m. and 5 p.m. to 9 p.m., with tickets starting at $44.73 including fees.

  • Lincoln Park Wine Fest: Lincoln Park Wine Fest returns to Jonquil Park (1001 W Wrightwood Ave) this weekend, Oct. 9–11, for its 10th anniversary. Visitors can sample wines from around the world while enjoying local food vendors, DJ music and shopping. Two-hour tasting sessions start at $30 for 12 wine samples and a souvenir glass. VIP tickets start at $67.50 and include five additional premium tastings and private seating. The 21+ festival runs Friday from 5–10 p.m., Saturday from 11 a.m.–10 p.m. and Sunday from 11 a.m.–7 p.m.

Poll Question of the Week

Will you be attending the Chicago Marathon this weekend?!

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Last Newsletter's Poll Results

Poll Results: Last week, we asked how you feel about October in Chicago, and here is how you voted:

  • 56%: One of my favorites

  • 23%: It’s fine

  • 15%: Best month of the year

  • 6%: Don’t like it

Sunrise & Sunset in Chicago

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

  • Sunrise: 6:55 a.m. (8 minutes later)

  • Sunset: 6:20 p.m. (11 minutes earlier)

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