Chicago Living

What To Do In Chicago This Fall

Fall is finally here in Chicago, although it doesn’t feel like it with the temps still in the high 80’s. Regardless, pumpkin spice is brewing, the leaves will be changing soon, and it’s time to start planning your Chicago fall itinerary. Whether you’re looking to do a staycation or visiting from out of town, there’s something for everyone this season.

Visit A Fall/Halloween Festival

Pier Pumpkin Nights

Date: Oct 1st – Oct 31st

This Navy Pier pumpkin fest will be back again this year. “Pier Pumpkin Lights returns to Navy Pier starting Saturday, Oct. 1. As part of the experience, guests will have the opportunity to explore a variety of pumpkin pop-up installations and enjoy Pier-wide deals during the month-long seasonal celebration.”

Jack’s Pumpkin Pop-Up

Date: Sept 22nd – Oct 31st

Photo opps, corn mazes, pumpkins, axe throwing, food and drinks: That’s what you’ll find at this yearly festival held near Goose Island. This is perfect for adults and families. Don’t forget to grab a pumpkin on the way out!

Party At The North Halsted Halloween Parade

Date: October 31st
Party in Boystown at the 25th annual North Halsted Halloween Parade. Rated top ten Halloween’s by Fodor’s travel guide & in Redfins best cities for Halloween, this rowdy fest parade a costume contest with prizes, performers, and more.

Eat & Drink At A Restaurant With All The Fall Vibes

Park And Field

This restaurant patio is great all year ’round, but I love visiting during the fall. They have fire pits, fun games, football watch parties, and more. This year for fall they’ll have Kids Halloween, Dogs Halloween, Hot Boozy Drinks, and s’mores!

Whiskey Business

This spot has great food and drinks, but the best part is definitely the rooftop. They usually have heaters and in the fall, they do movie nights on the roof! Last October they did spooky movies, so keep a look out for that.


This West Town Spot is one of the most unique in the city. Their comfort food is perfect for cooler weather. Their decor is cozy and rustic – it reminds me a bit of a ski-lodge. But if you want a truly unique (and surprisingly affordable) experience, grab some friends and try their whole animal experience. You won’t regret it.

Check Out An Oktoberfest

East Lakeview Neighbors Oktoberfest

Date: September 25th

This Lakeview Oktoberfest features beer, a pig roast, traditional German food, and a band. You can catch this fest at Murphy’s Bleachers in Wrigley.

The Northman Beer & Cider Garden

Date: Fridays, Saturdays, and Sundays Sept 16-Oct 2

This Riverwalk spot is the perfect spot to take in the fall downtown views and enjoy some beer German food, cider, and live music.