The best things to do in Chicago this November

Meet D’Andre Swift at Jake Melnick’s on November 9 and try his new Da Swift Picks menu. If you’re looking for a one-night-only Chicago sports-and-food crossover, Jake Melnick’s Corner Tap is launching a limited ‘Da Swift Picks’ menu created with Bears running back D’Andre Swift—and hosting a fan meet-and-greet with Swift on Monday, November 9, 2026 in Chicago.

Visit Tacama the titi monkey at the Helen Branch Primate House and enjoy the zoo’s Fall Fest with free entrance through November 1. Over at Lincoln Park Zoo, you can see its newest resident—a 14-year-old Bolivian gray titi monkey named Tacama—then stick around for the annual Fall Fest, running through November 1, 2026. The festival includes free entrance plus rides, s’mores, pumpkin carving, and live entertainment. Some add-on activities and special events require tickets.

Parking downtown on November 5? Stan’s Donuts and Millennium Garages are teaming up to give away 2,000 individually wrapped Mini Chocolate Dipped Donuts to commuters who park at the garages. The giveaway starts at 7:30 a.m., with 500 donuts available at each of the four locations while supplies last.

Fill your November calendar without emptying your wallet. The Chicago Cultural Center offers film screenings and creative workshops to keep your culture fix going all month. Elsewhere, teens ages 13–18 can get creative at Lincoln Park Zoo’s Plants & Prints program on November 7. Check individual listings for admission details, availability, and registration requirements before heading out.

Grab a cheese pizza at Little Nero’s — Home Alone vibes and festive cocktails await! If you’re looking for a fun November outing in Chicago, Easy Street Pizza will transform into Little Nero’s from mid-November to mid-January, serving movie-themed food, festive cocktails, and floor-to-ceiling Home Alone decorations. Reservation requests are accepted by email for the Park Ridge and Portage Park locations, and Fridays are walk-in only.

Plan a weekend getaway to Trego, Wisconsin, where the Wisconsin Great Northern Railroad offers an adults-only Holiday Wine Train lounge car aboard its Santa Pizza Train. Tickets cost $75 per person and include a bottle of Door Peninsula Winery wine, a souvenir tumbler, hors d’oeuvres, and holiday music. Rides run Friday through Sunday from November 13 through December 20, and Trego is roughly a six-hour drive from Chicago.

If you’re looking for a can’t-miss evening outing this month, Morton Arboretum’s annual Illumination light show returns this fall, opening to the public on November 14.

The 2026 celebration is the arboretum’s most ambitious yet, featuring a Northern Lights-inspired canopy and more than 22 light displays.

Christkindlmarket opens November 20 — three locations, free to visit. For a classic Chicago November outing, Christkindlmarket returns on November 20, 2026, with markets at Daley Plaza, Aurora’s RiverEdge Park, and Wrigleyville’s Gallagher Way. The flagship Daley Plaza market celebrates its 30th season, and all three markets are free to visit.

Tickets are on sale now—fixed-date tickets $7–$12 and flexible passes $20. If you’re looking for a classic Chicago winter outing, Lincoln Park ZooLights returns November 20, 2026–January 3, 2027, transforming the zoo with more than 3 million lights, dozens of LED displays, fire pits, a ferris wheel, seasonal drinks and snacks, plus select-night entertainment.

For a downtown Bears watch this November, Timothy O’Toole’s Pub has wings, pub food, and a football-focused atmosphere. The Streeterville spot is where you want to be for a traditional sports-pub outing.

Step into Cleopatra’s world with holograms, VR and original artifacts. This immersive exhibition at EXP Rosemont brings Cleopatra’s world to life with original artifacts, glasses-free 3D holograms, 360° projections, AR/VR and an interactive metaverse. The show opens on November 20, 2026 — join the waitlist for early access to tickets.

The corned beef on rye at Manny’s is non-negotiable — juicy, tender, and piled high. When you want a quintessential Chicago bite this November, Manny’s Cafeteria & Delicatessen delivers. It’s a fourth-generation, cafeteria-style Chicago deli founded in 1942, renowned for its piled-high corned beef on rye and crispy potato pancakes. Located in the Near West Side, it remains a beloved local institution known for generous portions and nostalgic service.

Sip coffee surrounded by vintage horror collectibles and classic cereal bowls. For a November outing with a little edge, head to The Brewed, a retro, horror-movie–themed cafe in Avondale at 2843 N. Milwaukee Ave. Along with espresso drinks, you’ll find bowls of classic cereal, vintage collectibles, and even a photo booth. It’s also conveniently across the street from The Horror House, a year-round shop for horror apparel, figures, and memorabilia.

Not every November plan has to involve pumpkin patches and a packed calendar. If your idea of self-care is putting down your phone and leaving your to-do list behind, AIRE Ancient Baths Chicago offers a slower-paced escape—without leaving the city. Tucked inside a restored 1902 factory in River West, the nearly 20,000-square-foot space invites you to wander between thermal baths at different temperatures, entirely at your own pace. And a newly added dry sauna brings another relaxing stop, while adding a massage gives you an excuse to linger a little longer.

If you’re looking to squeeze another iconic attraction into your November plans, head to the Adler Planetarium. Look through a telescope in the Doane Observatory, the largest public telescope in the state. Best of all, Illinois residents can enter for free on November 9, 10, 16, 17, and 18, 2026.

For a classic November outing in Chicago, head to one of the most celebrated museums: the Art Institute of Chicago. Since its founding in 1879, the Art Institute of Chicago has grown into one of the world’s most recognized art museums.

Illinois residents can enter for free on November 19, 2026. Advance online registration is required, and you need proof of residency.

Trade November’s chill for tropical greenery at Garfield Park Conservatory on Chicago’s West Side. Explore lush indoor gardens, desert plants, and seasonal displays beneath its glass roofs. Admission is free for Chicago residents with proof of residency; fees apply to most nonresident visitors. Advance reservations are strongly recommended.

Choose between Chicago Thin & Crispy and New York-style pies at Pizzeria Gabbo. For a new fall opening to add to your November food plans, check out Pizzeria Gabbo—a 60-seat neighborhood pizzeria and bar from Lettuce Entertain You Restaurants. The menu centers on Chicago Thin & Crispy and a New York-style crispy pizza, plus antipasti, pastas, salads, and soft-serve gelato.

Cruise Chicago’s skyline from the warmth of a floating hot tub. For a uniquely cozy November outing, Chicago Electric Boat Company’s Hot Tub Boats return for the winter season, offering a cruising hot-tub experience with underwater lights, Bluetooth speakers, and a BYOB policy for a city-views spin on the water.