Adventure Collective
Explore Chicago Like Never Before with Private Group Walking Tours - Chicago

Explore Chicago Like Never Before with Private Group Walking Tours

Chicagoeasy

Difficulty

easy

Duration

2–4 hours

Fitness Level

Suitable for most fitness levels; involves continuous walking on paved city streets.

Overview

Unlock Chicago’s secrets with a private group walking tour tailored to your interests. Experience the city’s iconic landmarks and hidden corners with expert local guides, away from tourist crowds.

Walking Tour
Chicago, Illinois

Book a Private Tour for Your Group!

Call Hillary at 312-799-0164 to arrange your private tour!

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Adventure Photos

Book a Private Tour for Your Group! photo 1

About This Adventure

Whatever the size of your group, Inside Chicago Walking Tours' engaging, fully customizable tours are a great option for a group activity. Because each client's interests are different, we customize experiences for that client — no two private tours are alike! Here are a few examples of private tours we've done for a wide range of client types:

-- A couple wanting to spoil themselves with a day-long private tour;

-- A family reunion of 20 people, meeting in Chicago from around the country;

-- A corporate outing of 40 people who work in downtown Chicago and had never bothered to get to know the area outside of work;

-- A large group of 120 people who wanted a 1-hour tour while their spouses and family were attending a conference event;

-- A jazz-themed corporate tour that focused on Art Deco architecture and ended with a private swing dance lesson;

-- A "gangster" tour for a small French group making their way across the country on Route 66.

Content-wise, clients usually prefer to leave it up to us, and we fill a couple hours with some of the best (and our favorite) things to see downtown. We recommend to clients that they check out our public tour route descriptions to get a sense of what they might like to see, and we mix and match from there, adapting to their interests. Whether it's exploring a different neighborhood, experiencing a "power hour" between other tourist activities, or building a tour around a special interest in some historical period or architectural style, we are highly skilled at constructing and presenting tours that delight all visitors. The bigger the group, the lower the price for everyone!

Want to get started or simply get more information? Feel free to get in touch by calling Hillary! You can reach her at 312-799-0164.

Tour Route Ideas... For ideas about what's possible for private tour content, check out our current public tour routes, which can all be offered as private tours, or which might give you some inspiration for what you'd like to see on your customized private tour.

Adventure Tips

Wear Comfortable Walking Shoes

Chicago’s urban terrain is best enjoyed with sturdy shoes that can handle pavement and occasional uneven surfaces.

Bring a Water Bottle

Stay hydrated while exploring, especially during summer months when the city can get warm and humid.

Check Weather Forecast

Chicago’s weather can change quickly; dress in layers to stay comfortable throughout your tour.

Plan for Traffic and Transit

Allow extra time for arrival and departure as Chicago’s busy streets and transit can cause delays.

Local Insights

Wildlife

  • Urban peregrine falcons nesting on skyscrapers.
  • Resident Canada geese along the lakefront.

History

Chicago's architecture boom followed the Great Chicago Fire of 1871, propelling it to become the birthplace of the modern skyscraper.

Conservation

The city emphasizes sustainable tourism and maintains extensive green spaces like Millennium Park to support urban biodiversity and reduce environmental impact.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Comfortable Walking Shoes

Essential

Vital for navigating city streets and ensuring a comfortable tour experience.

Weather-Appropriate Clothing

Essential

Layered clothes work best to adapt to Chicago’s variable weather conditions.

all specific

Reusable Water Bottle

Essential

Keep hydrated during warmer days on the tour.

summer specific

Small Backpack

Helpful for carrying water, snacks, and other personal items during your walk.