30 Fun Things to Do in Chicago in November

November is an underrated time to visit Chicago. Sure, you never know whether you’ll encounter glowing fall weather or an early snow. However, the city is still bustling with seasonal activities, sports events, festivals, and more. The big summer tourist crowds are replaced by visitors excited to enjoy Chicago’s holiday season. 

I’ve lived in Chicago for nearly two decades, and I’ve written two books about Chicago. I find that November is a less crowded and more affordable time in Chicago. Whether you’re visiting Chicago in November or you live in Chicagoland, here are 30 fun things to do in Chicago in the fall.

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Fun Things to Do in Chicago in November

1. Take a Nature Walk at the Chicago Portage

Chicago wouldn’t be the city it is today without its waterways, and we wouldn’t have linked to them without the Native Americans who shared the connection between the Chicago River and the Des Plaines River with Father Jacques Marquette and Louis Jolliet. Today, the Chicago Portage is a National Historic Site with a walking path and a monument.

2. Get Your Fortune Read With Cheese

You won’t find this anywhere else. A cheese fortune teller will teach you about the history of cheese magic and guide you to try it yourself. Read your fortune and then eat it!

3. The First Nations Film and Video Festival – November 1-10, 2025

Honor National Native American Heritage Month by screening work from Indigenous directors at the First Nations Film and Video Festival. The festival takes place annually in May and November, featuring free screenings of films by directors from the United States, Canada, Mexico, Central America, and South America.

4. Hot Chocolate Run – November 2, 2025

Need some motivation to hit the pavement? What’s better than rewarding yourself for completing a 5K, 10K, or 15K in Grant Park with chocolate at the finish line? The Hot Chocolate Run delivers a mug with chocolate fondue, dippables, and hot chocolate! I ran the 15K years ago, but I would run a 5K today just to get to the chocolate faster.

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

5. 312 Comedy Festival – November 4 – 9, 2025

Have a laugh at six venues around Chicago during the 312 Comedy Festival. More than 20 performers feature during the week-long festival, including Fortune Feimster, My Favorite Murder, Earthquake, and more.

6. Sip a Cocktail in a Historic Chicago Speakeasy

Chicago leans into its Prohibition past with speakeasy-themed bars, but The Drifter’s space actually operated as a speakeasy during Prohibition! Learn how to find the secret entrance inside Chicago’s Oldest Tavern.

7. Chicago Humanities Fall Festival – November 5-13, 2025

The Chicago Humanities Festival brings together notable names in arts, culture, and politics for an inspiring series across the city. Don’t miss conversations with Salman Rushdie, Margaret Atwood, and Cheech Marin.

8. Wine Stroll at Lincoln Square – November 6, 2025

Taste your way through Lincoln Square during the biannual Wine Stroll. Choose from four routes as you stop at local businesses from 6-9 p.m. and try a variety of wines along the way.

9. Black Harvest Film Festival – November 7-16, 2005

The Black Harvest Film Festival highlights Black films across the diaspora at the Gene Siskel Film Center in the Loop. The 31st annual festival features more than 70 films from 50 filmmakers.

10. Festival of Wood and Barrel-Aged Beer – November 7-8, 2025

Taste the rarest and most exclusive wood and barrel-aged beer, cider, mead, and perry at the Festival of Wood and Barrel-Aged Beer. More than 150 brewers from around the country will compete at Credit Union 1 Arena on the Near West Side.

11. Empty Bottle 33 ⅓rd Anniversary Concerts – October 31-November 10, 2025

In true vinyl fashion, the Empty Bottle celebrates its 33 ⅓rd anniversary with a slate of shows ranging from honky tonk to hardcore punk. Don’t miss Osees, Soul Glo, and the Pains of Being Pure at Heart, along with hometown favorites like Whitney and Melkbelly at the legendary Ukrainian Village Venue.

12. Sip with a View at Tea Around Town

If you’re looking for a unique girls’ day activity, consider dressing up for a tea party with your friends while admiring Chicago’s landmarks on a bus tour. Tea Around Town is a mobile tea party that blends gourmet bites and premium teas with a tour of Chicago hits like The Bean, Magnificent Mile, and more.

13. IllumiBrew at Morton Arboretum – November 14, 2025

Be the first to see the Morton Arboretum in Lisle glow with holiday light, color, and music for the Illumination: Tree Lights show. IllumiBrew is the official kickoff event featuring seasonal beers, ciders, meads, and cozy fires along the Illumination trail.

14. See Chicago Underground on a Pedway Tour

Savvy Chicagoans know to head underground if the weather is getting chilly, and now you can too. The Underground Pedway Tour guides you to hidden gems of Chicago architecture that even locals don’t know about in the Loop.

15. Lightscape at Chicago Botanic Garden – November 14 through January 4

Get your tickets early for Lightscape at the Chicago Botanic Garden. The popular holiday event transforms the grounds with a magical 1.3-mile trail of twinkling lights and showstopping displays expertly curated anew each year.

16. Christkindlmarket Chicago – November 21 – December 24

Chicago has more than one Christmas market, but this is THE Christmas market. You can’t celebrate the holiday season in Chicago without grabbing a mug of hot wine and European snacks, and shopping at the free Christkindlmarket.

17. Christmas Tree Lighting Ceremony – November 21, 2025 

Chicago has an official Christmas tree, and its tree lighting ceremony has been a city tradition for more than 100 years. The 112th City of Chicago Christmas Tree will be lit on November 21 at 6 p.m. in Millennium Park near Michigan Avenue and Washington Street, followed by a fireworks display.

18. Zoolights at Lincoln Park Zoo – November 21–January 4 

Lincoln Park Zoo has a festive transformation during ZooLights. The event features more than one million sparkling lights and seasonal displays like a holiday light tunnel. Admire the animals while you listen to carolers or sip hot chocolate.

19. A Night with Chicago Football Conference Champions – November 21

The Bears might not have championship prospects this season, but you can travel back to 2006 on this cruise. Join linebacker Brian Urlacher, quarterback Rex Grossman, and defensive standout Alex Brown football-focused night on Lake Michigan.

20. Ice Skating in Millennium Park – November 21, 2025 through February 2026

Chicago offers many parks where you can ice skate, but none are as iconic as twirling below the Bean in Millennium Park. The McCormick Tribune skating rink in Millennium Park offers the quintessential Chicago holiday experience. Admission is free, but you’ll need to reserve a time online. Bring your own skates or rent them here.

21. The Wintrust Magnificent Mile Lights Festival – November 22, 2025

Be dazzled by the nation’s largest nighttime parade at the Wintrust Magnificent Mile Lights Festival on Michigan Avenue from Oak Street to Wacker Drive from 5:30-7:15 p.m. The free festival includes the holiday parade, the lighting of Michigan Avenue’s trees, and a fireworks display.

22. Winterland at Gallagher Way – November 23 – December 31

Wrigleyville goes family friendly at this free Christmas market. Head to the park next to Wrigley Field for a holiday market, carnival rides, visits with Santa, and other seasonal activities at Winterland.

23. Chicago Thanksgiving Parade – November 27, 2025

Step aside NYC, Chicago has its own free Thanksgiving Parade down State Street. Get in the holiday spirit while colorful floats and live music take to the street from Ida B. Wells Drive to Randolph Street from 8 – 11 a.m. on Thanksgiving morning.

24. Chicago Thanksgiving Lunch Cruise on Lake Michigan – November 27, 2025

Why spend your day stressing in the kitchen when you can be cruising on Lake Michigan? This Thanksgiving Lunch Cruise boards at Navy Pier and delivers a chef-prepared turkey meal, live DJ, and views of Chicago’s iconic landmarks from the water.

25. Take the Family to Flyover

If you’re wondering what to do with your family visiting Chicago, give them a view they haven’t seen before at Flyover. The 30-minute immersive ride zooms you over the city’s iconic landmarks from new perspectives.

26. Turkey Trot Chicago – November 27

Support a good cause while running up your appetite on Thanksgiving morning at Turkey Trot Chicago. Choose from a 5K or 8K run in Lincoln Park at 7 a.m. before hitting the Turkey Day Tailgate of hot cider donuts. The race benefits the Greater Chicago Food Depository.

27. Let Someone Else Cook for Thanksgiving

Enjoy the biggest meal of the year without the stress by leaving the cooking to the professionals. Order Thanksgiving dinner in advance from local restaurants like the Publican, Daisies, and Goddess and the Grocer.

28. Wreathing of the Lions at the Art Institute – November 28

The Art Institute lions are Chicago icons, especially around the holidays when they sport Christmas wreaths. Watch the lions get wreathed to kick off the holiday season with live music and hot chocolate at 10 a.m. 

29. Peanuts Exhibit – Through January 4

See your favorite cartoon characters up close at Take Care with Peanuts The Exhibit. The exhibit at Navy Pier offers interactive displays emphasizing self-care, empathy, and environmental stewardship for visitors of all ages.

30. Yoko Ono: Music of the Mind – Through – February 22, 2026

Chicago is the only city in the U.S. where you can catch Yoko Ono’s “Music of the Mind” exhibit. The retrospective celebrates her career across 200 works of recordings, music, film, photography, and interactive works at the Museum of Contemporary Art.

Visiting Chicago in November FAQ

Is November a Good Time to Visit Chicago?

Fall might be my favorite time of year in Chicago. Sunny days and cooler temperatures make it a wonderful season for getting outside to enjoy the city’s parks and trails. There is a stacked calendar of food and cultural festivals, sporting events, and holiday activities across Chicago. The city is buzzing with holiday excitement, but you can find cheaper flights and hotel deals than you can during other times of the year. I recommend booking ahead, especially around the Thanksgiving holiday, for popular restaurant reservations and tickets to Chicago’s top attractions like the Field Museum, 360 Chicago Observation Deck, or the Art Institute, to skip the lines.

What is Chicago Weather like in November?

November in Chicago can deliver sunny fall weather or early snow flurries. According to the National Weather Service, the average temperatures in Chicago in November range from a high of 48 degrees to a low of 34 degrees. With the sun setting earlier due to the end of Daylight Saving Time, there is more of a chill in the air during the evening. The weather can shift rapidly, so be sure to check the forecast before you visit Chicago in the fall so you can pack accordingly.

What Should I Wear to Chicago in November?

If you’re wondering what clothes to wear to Chicago in November, I recommend packing layers. The days are typically warm and sunny, but you might experience a cool lake breeze off Lake Michigan. Check the weather before you visit Chicago in November so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the fall.

• Chicago is a walking town, so pack comfortable shoes like sneakers or boots.
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. Merino wool makes a great base layer for men and women. You may want to layer with a women’s flannel or a men’s flannel.
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped Breton shirt that I didn’t like.
• In the fall, I typically layer a lighter trench coat, leather jacket, or bomber jacket over my outfit.
• If the forecast calls for winter weather, pack a long jacket, preferably one made with down.
• It doesn’t hurt to pack a windproof travel umbrella for rainy days and a beanie in case it gets chilly at night.

Where to Stay in Chicago in November

Wondering where to stay overnight in Chicago in the fall? I love the views of Grant Park from the Blackstone Hotel and the iconic pool at the InterContinental. The Chicago Athletic Association has great views of Millennium Park’s fall foliage and a rooftop fire pit, while the LondonHouse boasts beautiful views of the Chicago River from its rooftop bar.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you get excited to visit Chicago in November!

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things to Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May
• What to Do in Chicago in June
• Fun Things to Do in Chicago in July
• What to Do in Chicago in August
• Fun Things to Do in Chicago in September
• What to Do in Chicago in October
• What to do in Chicago in December

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