Fall in Chicago brings a crisp change of wind, colorful leaves, and plenty of reasons to get out and enjoy the West Loop. Here are four great ways to soak up the season, with some sweet caffeine stops and festive Oktoberfest fun included.
1. Raise a Glass at Beers & Bites
Mark your calendar for Thursday, September 25, 2025, when Beers & Bites takes over the rooftop at Allium. Sip craft beers from eight different breweries paired with seasonal bites while soaking in skyline views, live entertainment, and the spirit of fall in West Loop. It’s one of the best ways to celebrate autumn evenings with friends, food, and community energy.
2. Start Your Mornings with Coffee & Pastries
Nothing says cozy fall like a warm latte and flaky pastry. In the West Loop, spots like Good Ambler Bakery & Café in Fulton Market are perfect: their pastry and coffee program is top notch, and the café offers a great vibe all week long.
If you want something a bit more offbeat, try Vietfive Coffee — bright, airy space, Vietnamese-inspired drinks, and tasty pastries & bánh mì-style snacks. Perfect for laptop hours or a relaxing weekend treat.
3. Outdoor Walks, Markets & Local Shopping
With cooler temps, the West Loop’s mix of industrial architecture, leafy streets, and art galleries feels extra special. Take walks around Fulton Market, drop into the Randolph Street Market at the end of the month, or just wander side streets, admiring murals and pop-ups. These strolls pair beautifully with a coffee stop or two, and there’s always something new to discover weather permitting.
4. Dive Into Oktoberfest & Fall Festivities
Autumn in Chicago means Oktoberfest is everywhere, and West Loop is no exception. A few events to watch:
Haymarket Pub & Brewery’s Oktoberfest, September 27: German-style lagers, sausages on the grill, live music and festive decor in the heart of West Loop.
Guinness’ West Loop Oktoberfest (September 12-14): Think Bavarian food specials, live music including polka and traditional bands; stein-hoisting contests, pretzels & more.
Fulton Market Oktoberfest at PBJ West Loop: For more casual but still vibrant festivity, food, drink, and fun in the Fulton Market area.
No matter how you like to enjoy fall, the West Loop has options for everyone.