BEST DATE NEWS

Nov. 5, 2026: Best Date News Volume #203

Welcome to Best Date News, your go-to guide for what's happening in Chicago! This week, we're diving into fall weather, the holiday season, Chicago Christmas trees, Redhot Ranch, Rainbow Cone pies, weekend events and more.

Via Chicago Bears

Nov. 5: National Holidays

  • National American Football Day

  • National Doughnut Day

  • National Chinese Takeout Day

  • National Love Your Red Hair Day

  • National Bonfire Night

Sponsored by our friends at Lettuce Entertain You

Via Lettuce Entertain You

Lettuce Entertain You’s Holiday Bonus is Back!

  • Lettuce Entertain You: One of Lettuce Entertain You's popular holiday promotions just returned. For a limited time, when you purchase $100 in Lettuce Gift Cards, you'll receive a FREE $25 Holiday Bonus to use at participating restaurants.

  • With 90+ Lettuce restaurants nationwide, including Sushi-san, Aba, RPM Italian, Shaw's Crab House and Crying Tiger, there's something for everyone. From casual neighborhood spots to upscale dining experiences, one gift card gives recipients plenty of options to choose from.

  • Not sure what to get someone for the holidays? A restaurant gift card is a great option, especially for people who would rather go out for a nice meal than receive another physical gift. Lettuce Gift Cards never expire and are available as physical cards or digital eGift Cards. They can be used for dine-in, carryout and online pickup.

  • The promotion runs through Dec. 30, and the $25 Holiday Bonus can be redeemed from Jan. 2 through April 15 for dine-in or direct carryout at participating Lettuce restaurants. Get your holiday shopping done early and take advantage of this limited-time offer.

Chicago News

  • Fall Weather is Here: After Chicago's sixth-warmest October on record and temperatures reaching the 70s earlier this week, we're finally getting a taste of late fall weather. A significant cooldown arrives today, Thursday, Nov. 5, with highs in the 50s and wind gusts reaching 30 mph. Friday will be even colder, with highs in the upper 40s and the possibility of frost or freezing temperatures overnight into Saturday. The good news? We're expecting a couple of nice, sunny days with temperatures in the upper 50s and low 60s starting Sunday.

  • Chicago Christmas Tree: Chicago's official Christmas tree arrived at Millennium Park yesterday, and we were there to watch it get lifted into place by a crane. This year's tree is a 50-foot Norway spruce from Glenview, Illinois. Over the next couple of weeks, it will be decorated ahead of the 113th Annual City of Chicago Christmas Tree Lighting Ceremony on Friday, Nov. 20 at Millennium Park. Speaking of Millennium Park, the fall colors are popping right now.

  • OpenTable’s Top 100: Chicago continues to prove why it's one of the best food cities in the country. OpenTable just released its annual list of the Top 100 Restaurants in America for 2026, and 12 Chicago restaurants made the cut, the second most of any city in the country behind New York City. The list was compiled using more than 11 million verified diner reviews and restaurant reservation data from across the country. Check out the list to see which 12 Chicago restaurants earned a spot.

  • Redhot Ranch: Chicago favorite Redhot Ranch just opened a new location in Downers Grove at 60 Ogden Ave. This marks the restaurant's second suburban location, joining its other suburban spot in Skokie and three locations in Chicago. Known for its affordable burgers, hot dogs and fried shrimp, the restaurant offers burger and fries combos under $7 and hot dog and fries combos under $6. The new location is cash only and open daily from 10:30 a.m. to midnight.

  • Rainbow Cone Pies: Chicago's iconic Rainbow Cone is celebrating its 100th anniversary with a brand-new dessert. The ice cream shop just introduced ice cream pies featuring its classic five-flavor Rainbow Cone combination, Chocolate Obsession and a customizable option. You need to see what these colorful new pies look like. Slices cost $4.99 and whole pies are $26.99, with both available year-round. Rainbow Cone also added three limited-time candy cane treats for the holidays, available through Dec. 31.

Via Starbucks

Just for Fun

  • Starbucks Holiday Menu: Starbucks kicked off the holiday season today with the return of its festive drinks, treats and cups. Favorites like the Peppermint Mocha, Caramel Brulée Latte and Sugar Cookie Latte are back, alongside new drinks like the Tiramisu Velvet Latte and Apple Pomegranate Refresher. The new limited-edition glass Christmas tree cup is already generating a ton of excitement, with the viral Bearista Glass Cold Cup also returning on Dec. 1. Red Cup Day is Tuesday, Nov. 17, when customers can get a free reusable red cup with the purchase of a handcrafted holiday drink while supplies last.

  • November Holiday Events: November is always one of the busiest months of the year in Chicago as the city comes alive with holiday activities, festive celebrations and more. From Christmas tree lighting ceremonies and holiday markets to parades and fireworks, we rounded up seven free holiday events and attractions happening throughout November that you won't want to miss.

  • Chicago Bears: The Chicago Bears host the Tampa Bay Buccaneers this Sunday, Nov. 8, at Soldier Field for Sunday Night Football, with kickoff set for 7:20 p.m. The Bears have won three straight games, and newly acquired All-Pro defensive tackle Jeffery Simmons will play his first home game since being traded from the Tennessee Titans. In other Bears news, Chicago boutique Alice & Wonder has a Bears collaboration launching tomorrow, Friday, Nov. 6, at 10 a.m.

  • Best Italian Food: Think you know all the best Italian restaurants in Chicago? You might want to see what the experts have to say. Time Out Chicago recently put together a guide to Italian food in Chicago, featuring recommendations for the best pizza, red-sauce restaurants, upscale Italian dining, bakeries, delis and more from six local chefs, including those behind Daisies, Adalina and Sapori Trattoria. See which spots the chefs recommend.

  • Free Museum Days: Looking for something free to do this November? Illinois residents can take advantage of 21 free museum days across six of Chicago’s most popular museums this month. Take a look at our November free museum days roundup to see all the dates and start planning your next museum visit.

Sponsored by our friends at Buckhorn Whiskey

Via Buckhorn Whiskey

A Free, Secret Whiskey Event is Coming to Bucktown!

  • Buckhorn Whiskey: A secret whiskey-themed experience is taking over a Bucktown bar tomorrow, Friday, Nov. 6, and it's completely free to attend, as long as you know about it and secure an RSVP. Buckhorn Whiskey is hosting the Buckhorn Buck Hunt, a private scavenger hunt-inspired whiskey adventure from 5–8 p.m.

  • From the outside, the bar will look like any other neighborhood watering hole. Once you step inside, however, you'll find a space transformed into a rustic hunting lodge, complete with autumn foliage, woodland decor and an outdoorsy atmosphere. The exact location is being kept a secret, and guests must RSVP to unlock the coordinates.

  • Guests will also get to discover Buckhorn's lineup of flavored whiskeys and ready-to-drink whiskey lemonades, including the all-new Buckhorn Smoked Maple. The new American whiskey brand from Sazerac is bringing its no-frills approach and signature "Buck-It" attitude to Chicago for a Friday night experience filled with unexpected discoveries.

  • Ready to ditch your usual Friday plans? Admission to the Buckhorn Buck Hunt is completely free, but registration is required. Guests must be 21 or older and show a valid ID at the door. Sign up here to get your name on the list, discover the secret Bucktown location and join the hunt.

Via 312 Comedy Festival

Weekend Plans

  • 312 Comedy Festival: Chicago's 312 Comedy Festival kicks off today, Nov. 5, bringing 11 days of comedy to seven venues across the city through Nov. 15. This year's festival features 39 different shows, including performances from some of the biggest names in comedy like Nikki Glaser (Nov. 13–15), Bert Kreischer (Nov. 6–7), Joey Diaz (Nov. 5) and Ron White (Nov. 8), among many others.

  • Autumn Restaurant Weeks: Andersonville is hosting its second-ever Autumn Restaurant Weeks from Nov. 1–15, featuring cozy fall flavors and specialty prix fixe menus from local restaurants. Similar to Chicago Restaurant Week, the event features 14 participating restaurants offering multi-course brunch, lunch and dinner menus, with prices starting at $30.

  • MSI Tree Lighting: Griffin Museum of Science and Industry kicks off the holiday season this Saturday, Nov. 7, with its annual Tree Lighting and Cultural Festival, included with museum admission. The event marks the start of the Christmas Around the World and Holidays of Light exhibit, featuring more than 50 trees decorated to represent different countries and holiday traditions. The four-story Grand Tree will be lit for the first time this season, with cultural performances and treats from Stan’s Donuts.

  • Macy’s on State: The holiday season kicks off at Macy’s on State Street this Saturday, Nov. 7, with the 119th annual Great Tree Lighting at noon inside the Marshall Field’s Walnut Room. The 45-foot tree features more than 2,000 ornaments and 6,600 lights. From noon to 5 p.m., visitors can enjoy festivities throughout the store, including holiday crafts, Frango chocolate samples, live music and complimentary gift wrapping. The celebration also marks the opening of the Holiday Windows and Santaland, with the Holiday Square market opening Nov. 20.

  • Espresso Martini Fest: Hubbard Inn in River North is hosting an Espresso Martini Fest this Saturday, Nov. 7, from 5–8 p.m. The event is dedicated entirely to the popular coffee cocktail, with tickets including 15 espresso martini tastings, giveaways and more.

Poll Question of the Week

If you put up a Christmas tree, when do you do it?

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Last Newsletter's Poll Results

Poll Results: Last week, we asked your preferred trick-or-treating candy combination. Here is how you voted:

  • 40%: Reese’s Peanut Butter Cups and Kit Kats

  • 33%: Snickers and Twix

  • 15%: M&M’s and Skittles

  • 12%: Starburst and Sour Patch Kids

Sunrise & Sunset in Chicago

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

  • Sunrise: 6:27 a.m. (52 minutes later)

  • Sunset: 4:39 p.m. (1 hour and 9 minutes earlier)

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