Chicago day tours

Good things come in small packages, which is why most of our tours are capped at 12 people – with the exception of a few trips that can accommodate up to 16. That way, we don't overwhelm streets and local neighbourhoods and you get a more immersive experience.

You’ll find the maximum group size on the trip page.

All of our day tours are led by a local leader and include immersive activities to give you an authentic experience of a destination.

On our join-in tours, you’ll join a small group of up to 16 travellers at a set time, whereas a private tour is just for your party, with the option to choose your start time and request a hotel pickup if available.

Although our trips are inclusive of all costs and we ensure our guides and staff are paid fairly, if you’re happy with your experience, tipping your leader is always appreciated!

Many of our travellers book at the last minute, but of course, if there’s a tour you really want to do, it’s best to book in advance to secure your spot.

We’re committed to making our trips more inclusive for everyone. Some destinations are better suited to travellers with disabilities than others, but we’re always happy to chat and help you decide if a particular tour is right for you.

Where possible, we can look into making any reasonable adjustments or recommend an alternative tour.

Yep, you can choose another date or switch to a different tour up to 24 hours before your trip starts, as long as there's availability. Just get in touch with your booking reference and let us know what you'd like to change.

Plans can change, we get it! Both our join-in and private day tours are fully refundable up to 24 hours before the trip starts.

Any no-shows or cancellations made within 24 hours of the tour are subject to a 100% cancellation fee, as per our terms and conditions.

Want to cancel? Please email us with your booking reference.

Excluding tours with strict age limits – like cocktail, beer or wine-tasting experiences – many of our tours are open to children. You'll find the minimum age on the trip page.

Kids under six can usually join for free, but if you need to bring a stroller, please read the trip itinerary to ensure it’s accessible.

For most of our day tours, you’ll need to make your own way to the meeting point. Selected tours do offer hotel pickups when arranged in advance, so be sure to check the trip page to see whether this is available.

Chicago's weather is famously unpredictable, so dressing in layers is always a smart move. You’ll also need a pair of trusty walking shoes for exploring the riverfront and architecture around the city. If you’re here in summer, keep sunglasses and sunscreen within reach, while winter visitors will want a warm coat, gloves and a hat to tackle the city's icy winds.

Most locals will tell you summer (June to August) is when you’ll see the best of Chicago. Beaches, lakefront activities, rooftops and restaurants along the Riverwalk are in full swing, and there are heaps of free summer concerts in Millennium Park.

Spring offers milder temperatures, fewer crowds and spring blooms in Lincoln Park and the Botanic Garden, while autumn is great for experiencing how Chicago celebrates spooky season (spoiler: it goes all out!) and hitting up the Chicago International Film Festival.

Winters are cold, gray and snowy, but the city leans into it with cosy jazz bars, festive markets and, of course, plenty of deep-dish pizza.