Chicago’s urban landscape is famous for its towering architecture, deep-dish pizza, and the shimmering skyline. But beyond the city’s hustle, Chicago offers some surprisingly engaging hiking and trekking adventures that reveal its hidden stories and unique charms. Whether you’re interested in festive holiday strolls through glittering streets or spooky stories on a Halloween bike tour, there’s something that suits your style. These tours make it easy to explore the city’s character while staying active, all without the hassle of planning every detail yourself. And since most tours include local guides sharing insider stories, you gain a richer perspective that you might miss on your own.
For travelers seeking in-depth Chicago experiences, we’ve rounded up the best hiking and trekking tours. These options are carefully chosen to highlight different seasons, interests, and activity levels. Ready to explore? Let’s take a closer look at what each tour offers.
1. Chicago-Style Holiday Hike: Festive Food and Walking Tour
At number one, the Chicago-Style Holiday Hike: Festive Food and Walking Tour captures the magic of Chicago during the winter holiday season. For around $85 per person, this 3-hour tour takes you through Chicago’s beautifully decorated streets, with highlights like the Christkindlmarket, the iconic outdoor German-style holiday market. You’ll learn about Chicago’s holiday traditions while sampling generous tastes of Chicago foods and seasonal treats—think hot cider and brownie samples at the historic Palmer House Hilton, where the original deep-dish pizza was reportedly invented.
What makes this tour stand out is its focus on local holiday traditions combined with accessible, engaging storytelling. Visiting places like Macy’s holiday displays and Millennium Park’s outdoor ice skating rink, it offers a lively yet intimate experience capped at just 15 travelers. Visitors frequently praise the friendly guides, who share stories about Chicago’s architecture, history, and food. The tour’s value is excellent, especially considering the inclusion of tastings and a chance to see the city’s festive lighting and decorations up close. An optional VIP craft beer upgrade is available, perfect for those wanting a little extra cheer.
Bottom line: If you want a short, lively introduction to Chicago’s holiday spirit with tasty bites and holiday sights, this tour is a great pick. It’s especially suited for first-time visitors wanting a cozy, festive overview.
2. Fright Hike: Chicago Halloween Bike Tour
For those who prefer active adventures, the Fright Hike: Chicago Halloween Bike Tour offers a thrilling way to explore Chicago’s spooky side. Priced at about $55, this 3-hour small-group tour runs only around Halloween, making it a seasonal highlight. You’ll pedal through Chicago’s shadowy streets and eerie neighborhoods, listening to chilling tales of hauntings, tragedies, and infamous serial killers. Your bike, equipped with lights, keeps you safe as you cruise past haunted landmarks and hear stories most visitors never encounter.
This tour is ideal for active travelers who enjoy a bit of fright with their sightseeing. The comfort bikes and safety helmets ensure a smooth ride, and the guide’s storytelling creates a spooky atmosphere. Sample reviews mention how fun and informative the guide, Jamal, is, blending humor with chilling facts. The tour ventures into historic sites like the John Hancock Center and the Chicago Loop, turning the city into a haunted film set after dark.
Bottom line: If you’re looking for a unique, adrenaline-filled way to experience Chicago’s darker history, this Halloween bike tour delivers scares and stories in equal measure. It’s perfect for those comfortable on a bike and eager for spooky tales.
How to Choose Your Perfect Chicago Trekking Adventure
When deciding between these outdoor tours, consider your interests, activity level, and the time of year. The Holiday Hike offers a cozy, food-filled exploration during winter, making it ideal if you want to enjoy Chicago’s festive spirit with some gentle walking. Conversely, the Fright Hike is a great pick for thrill-seekers who enjoy biking and spooky stories, especially around Halloween.
If you prefer a guided walk with tastings and city sights, the Holiday Hike is a balanced option. For a more physically active, adrenaline-pumping experience, the Halloween Bike Tour offers a memorable way to see the city’s haunted side.
Booking early is recommended, especially for seasonal tours, and consider the weather—winter plans should include warm clothing, while October’s chills are perfect for spooky stories. Both tours provide a local perspective that elevates your experience beyond just walking or biking around.
In summary, Chicago’s outdoor tours offer a range of active, engaging ways to explore the city’s landscape and stories. The Holiday Hike is perfect for a festive, food-filled stroll, while the Fright Hike delivers a spooky adventure on two wheels. For those looking to combine activity with history, these options add depth and fun to your Chicago visit. No matter your choice, booking early will ensure a spot on these memorable excursions—so get ready to see Chicago from a new perspective.