private chicago tours

The Perfect Chicago Outing for Your Team or Group

Expert local guides. Fully private. Custom routes. One flat rate — perfect for corporate outings, intern programs, school trips, and group events.

Starting at $250 for groups up to 25 · Fully private · 2+ hours · Groups of 50+ welcome

★★★★★ 800+ Five-Star Google Reviews

🏆 2025 TripAdvisor Traveler’s Choice Winner

📍 Locally Owned & Operated Since 2015

WHO WE SERVE

Built for Groups. Designed Around You.

Whether you’re organizing a team outing or a school field trip, we’ve done this before — and we make the whole process easy from first inquiry to final step.

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Corporate Team Outings

Give your team something they’ll actually talk about. Fun, social, and genuinely interesting — a refreshing break from the conference room that doesn’t require you to be an event planner.

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Intern Programs

Show your interns Chicago the right way. Our guides know how to engage a crowd and bring the city alive for people who are new to town — one of our most popular summer bookings.

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School Field Trips

Educational, engaging, and easy to coordinate. We regularly work with schools from the greater Chicago area and know how to make history and architecture land with students.

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Group Visits & Events

Friends in town for a conference? Celebrating a milestone? We’ll build the tour around your group’s interests and make it a highlight of the trip.

THE PROCESS

Simple from Start to Finish

We’ve kept the process intentionally straightforward so you can check this off your list quickly.

1. Tell us about your group

Fill out our short inquiry form — takes about 2 minutes. We’ll ask about your date, group size, preferred time, and interests.

2. We confirm your guide & details

We’ll match you with one of our expert Chicago guides and follow up to confirm your date, route, start time, and any special requests.

3. Show up and enjoy

Your guide handles everything from there. Just bring your group and get ready to see Chicago differently.

WHAT WE OFFER

Popular Private Tour Experiences

Not sure what kind of tour fits your group? Here are our most popular themes.

The loop / downtown

Chicago Loop & Downtown Highlights

Architecture, history, and iconic landmarks in the heart of the city. Great for first-timers and groups visiting for a conference.

GRANT PARK / THE LOOP

Millennium Park & Public Art

The Bean, Crown Fountain, and the best of Chicago’s world-class public art scene. Scenic, social, and endlessly photogenic.

THE LOOP / RIVER NORTH

Chicago Riverwalk & History

One of the world’s great architectural cities, explored on foot along the Chicago River. A perennial favorite for corporate groups.

THE LOOP / RIVER NORTH

Crime, Gangsters & Chicago History

Al Capone, the St. Valentine’s Day Massacre, and the stories Chicago’s history books leave out. Always a crowd-pleaser.

STREETERVILLE / GOLD COAST

The Magnificent Mile

Chicago’s famous landmark corridor, with stories behind the buildings most people walk past every day.

NORTH SIDE

Lincoln Park & Old Town

Green space, Victorian architecture, and neighborhood character. A great choice for school groups and nature-curious crowds.

PRICING

Straightforward Pricing. No Surprises.

STARTING AT

$250

flat rate · up to 25 people · 2+ hours

A group of 25? That’s just $10 per person for a fully private, expert-guided Chicago experience.

Full payment due 72 hours before your tour date.

All major credit cards accepted.

What's Included

✓ Fully private tour — no strangers joining your group

✓ Your guide is exclusively yours for the full duration

✓ Flexible start time — morning, afternoon, or evening

✓ Tours operate rain or shine

✓ Move at your group’s pace — no rushing

Large group? We’ve got you covered.

We regularly accommodate groups of 50+ by running simultaneous tours with multiple guides — different routes, staggered starts, so groups never overlap. About 1 in 4 of our private tours involves more than one group. Just note your headcount in the form.

what people say

Don't Take Our Word For It

Over 800 five-star reviews on Google. Here’s what guests have said about experiencing Chicago with us.

					Tom took us on a lovely festive walking tour! My colleague and I had just one day to explore the city and this walking tour was the perfect way to see the sights, learn some history, and get a few... read more mandatory photos. Tom was knowledgeable and great company!				
Mari
 
					We had an amazing great architecture walking tour with Tom! Tom was an amazing guide and super informative and knowledgeable about the Chicago skyline. This tour is a really great way to see the city and get your bearings. I... read more highly recommend doing this walking tour with Tom - Tom explained he was an ex-teacher and it shows from his calm demeanour, knowledge sharing and engagement!				
Phillip
 
					Tom was an awesome guide 🥰, a lot of architecture info, thank you so much! As we arent from Usa, didnt get some of the local sport comments 🤭. Thank you as well for making some stops with seating while... read more talking about the history and buildings! (Much appreciated)				
Julieta

get started

Request Your Private Tour

Fill out the form below and we’ll follow up to confirm guide availability and finalize your details.

Private Tour

Your Name(Required)

First Last

Email Address(Required)

Phone

Optional — for faster coordination

Organization

Optional

Group Size(Required)

Preferred Tour Date(Required)

Back Up Date

Optional but helpful

Preferred Time of Day(Required)

Tour Theme / Interest

Additional Details

Tell us about your group, any special requests, or questions. If you selected Custom above, describe what you have in mind.

Pricing Agreement(Required)

I understand this is a private tour starting at $250 for the group, with full payment due 72 hours before the tour date.

QUESTIONS

Common Questions

How far in advance should I book?

We recommend reaching out at least 1–2 weeks before your preferred date. That said, we can sometimes accommodate shorter notice, so don’t hesitate to inquire even if your date is coming up quickly.

What if our group is larger than 25?

Not a problem — about 25% of our private tours involve groups larger than 25. We accommodate larger groups by running simultaneous tours with multiple guides using different routes or staggered start times. Just note your headcount in the form and we’ll build a custom plan.

Can we customize the route?

Absolutely. The inquiry form has a field for your interests, and our guides are flexible, knowledgeable locals — not performers reading from a script. If you have something specific in mind that isn’t on our list, just describe it and we’ll let you know if we can make it work. There is typically an extra fee for customizations.

What if it rains?

Tours operate rain or shine. Chicago weather is part of the experience. We recommend layers and comfortable walking shoes regardless of forecast — and honestly, some of our most memorable tours have happened on overcast days.

When and how do we pay?

Payment is collected after we’ve confirmed your tour details and you’re ready to lock in your date. Full payment is due 72 hours before the tour. We accept all major credit cards.

Why choose you over other tour companies?

We’ve been doing this since 2015 and have earned over 800 five-star Google reviews and five consecutive TripAdvisor Travelers’ Choice Awards. We’re Chicago’s only locally owned free walking tour company — our guides are passionate Chicagoans who genuinely love this city. One price, no surprises, easy to work with.

Ready to Plan Your Chicago Outing?

It takes about 2 minutes to submit an inquiry. We’ll handle the rest.