By popular request on IG, I’ve put together a list of budget-friendly and splurge-worthy fall date night ideas in the city! From free to ticketed event, I wanted a little something for everyone. I hope you find this useful and I’m super eager to hear your thoughts. Some ideas have a fall theme, while others are more general. 

Here’s my Fall 2024 list of ideas for date nights in Chicago!

🧡 Celebrate Oktoberfest

Chicago has no shortage of Oktoberfest celebrations! Here are just a few listings that I found!

• East Lakeview Neighbors Oktoberfest Sep 15
• Oktoberfest Chicago Lakeview Sep 27-29
• Guinness Brewery Oktoberfest Sep 27-29
• Oktoberfest at Brookfield Zoo Sep 28

🧡 Visit Fall Fest at Lincoln Park Zoo

The Lincoln Park Zoo will host Adults Night Out: Howl-o-ween on Oct 24. Their annual Fall Fest runs Fridays-Sundays from Sep 27-Oct 27 and is always free to enter!

🧡 Attend Hyde Park Jazz Festival

The Hyde Park Jazz Festival happening on September 28th and 29th is a beloved event in Chicago that celebrates the timeless charm and exciting future of jazz music. Then take a walk before the festival and stop by 57th street books, Sip and Savor coffee, Daisy Po’boy, The Silver Room and more! There are a lot of independent bookstores in the area and you can see the full list here.

🧡 Have fun at Apple Fest, Farms & Orchards

The Lincoln Square Ravenswood Apple Fest runs Oct 5-6 this year! I also have a big list of apple-picking and pumpkin farms over here!

🧡 Go behind the scenes with Open House Chicago

If you have never done Open House Chicago with the Chicago Architecture Center, I highly recommend it! It’s happening October 15th-16th this year. This is your chance to explore buildings and parts of the city that are usually closed to the public and learn its history, etc. It’s FREE and a really cool way to explore the city. Many of the sites will indicate if they are family-friendly, accessible, etc. This is an awesome way for tourists and residents to explore the city! Tickets are required to reserve your spot and some locations sell out quickly.

🧡 Attend the Arts in the Dark Parade

The Arts in the Dark Parade celebrates the city’s art scene with a nighttime parade with awesome floats, cool puppets, and light installations. The parade is on Oct 19 and marches State Street from Lake to Van Buren.

🧡 Experience the Under the Dome Concert

Enjoy a concert under the magnificent Tiffany dome, the largest of its kind in the world. The Under the Dome Concert at Chicago Cultural Center, on Oct 24, is seriously a magical experience!

🧡 Cozy up at the October Cafe

The October Cafe in Norwood Park is the cutest fall-themed coffee shop!! We got their coffee flights and loved the welcoming, inclusive vibes! It’s so cute!

🧡 See a Halloween Movie

If you haven’t been to the iconic Music Box Theatre, it’s a Chicago landmark! The cinema has so much history. Their annual Music Box of Horrors film festival begins on Oct 19.

Other fun places for spooky movies are the Chitown Movies drive-in in Pilsen and the Rooftop Cinema Club in the West Loop.

🧡 See a candlelight concert

Speaking of the Music Box, we saw a Candlelight Concert there last year and had such a great time! Pro-tip: parking can be tricky on weekend nights, but the Brown Line stop at Southport is super convenient. Afterward, we grabbed a bite at Little Goat Diner and ice cream at Jeni’s. Check Fever’s listings since tickets sell fast! I also want to try one of their unplugged shows at AIRE Rooftop!

🧡 Visit the Day of the Dead exhibit at NMMA and explore Pilsen

Pilsen is one of our favorite neighborhoods for the food and culture! Take a walk to see all the street murals, explore the Día de Muertos exhibit at the National Museum of Mexican Art (opening Sep 20), and then have dinner at 5 Rabinitos or La Mejikana. End the night at a nightcap at La Luna or Del Toro. I have a whole itinerary that includes a day in Pilsen here if you want even more ideas!

🧡 Kibbitznest: books, brews, & blarney

Kibbitznest is a quirky little bar and bookstore hybrid in Lincoln Park that encourages board games and socializing over electronics and wifi.

🧡 Take a ghostly walking tour

The Chicago Gangsters and Ghosts Walking Tour is a two-hour tour through the Loop and Riverwalk. It’s part history lesson, part ghost stories, and would be such a fun date!

🧡 Take a pasta-making class

Get cozy in a class at Tutore Italian Cooking School! I have heard nothing but amazing things about this experience! You can choose between classes like Gnocchi 101, Italian Christmas Cookies, or Pasta 101.

I hope this helps with date night ideas in Chicago this fall! I’ve got more fun activity recommendations in my Fall Bucket List Roundup here!

Christine