3 Things to do Chicago Illinois in Oct/Nov

Chicago in the fall is truly a sight to behold, and if you're planning a trip for October or November, you're in for a treat! The city transforms with vibrant autumn colors, and there's a unique crispness in the air that makes exploring even more invigorating. I recently spent some time there, and I'm excited to share a few more in-depth recommendations to make your fall visit unforgettable. First up, you absolutely have to bike along Lake Michigan. The views of the skyline are always stunning, but seeing the trees along the shore bursting with fiery reds, oranges, and golds during the changing foliage season is something else entirely. You can easily rent a bike for around $15 for a few hours – I often use the Divvy bike-sharing program, which has stations all along the lakefront path. It’s a fantastic way to cover ground, feel the breeze, and get those iconic Chicago photos. Don't forget to bundle up, though; that lake breeze can be surprisingly chilly! For a truly magical experience, mark your calendar for the Jack-o'-lantern displays at the Chicago Botanic Gardens. They host events featuring thousands of artist-carved pumpkins, sometimes even up to 1,000 Jack-o'-lanterns, creating breathtaking illuminated trails. It feels like stepping into a whimsical autumn wonderland! Tickets are usually around $25-27, and they often sell out quickly, so I highly recommend booking well in advance, especially for popular dates like October 15-19 or October 22-26 sessions. The Botanic Gardens are a bit north of the city, so factor in travel time, but it's totally worth the journey. If you're looking for a relaxing evening with spectacular views, find a cozy spot with a rooftop view of the Chicago skyline. Many hotels and restaurants offer fantastic patios. While the original content hints at hot chocolate for chilly nights, many places also offer a great selection of local beers or warm autumnal cocktails. Imagine sipping a warm drink as the city lights twinkle below – it's such a perfect end to a day of exploring. My personal go-to spots include places near the Chicago River for direct views of the iconic architecture. Families or anyone looking for some classic fall fun should definitely check out the Fall Fest at Lincoln Park Zoo. The zoo itself is free, which is amazing, and during Fall Fest (usually running until late October, like October 26th this year), they have special events, rides, and various pop-ups that create a lively, festive atmosphere. It’s a fantastic way to enjoy the autumn weather, see some animals, and participate in seasonal activities without breaking the bank. Always check their website for the most current schedule! Finally, for the craft beer aficionados, the Festival of Wood and Barrel Aged Beers is a must if your trip lands around November 7th-8th. It's a premium event, with tickets typically around $85, but it offers a unique opportunity to taste a wide variety of rare and exquisite barrel-aged beers and ciders. It's a more adult-focused event with live music, creating a really vibrant social scene. It’s definitely a splurge, but for those passionate about craft brews, it's an unparalleled experience. No matter what you choose to do, remember to dress in layers for Chicago in the fall – the weather can be quite unpredictable! And of course, no trip to the Windy City is complete without indulging in some deep-dish pizza to warm you up after a day of adventures. Enjoy your autumn escape to Chicago!