Adventure Collective
Explore Chicago’s Iconic Architecture on a Private Highlights Tour - Chicago

Explore Chicago’s Iconic Architecture on a Private Highlights Tour

Chicagoeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Basic fitness required; suitable for most adults comfortable with walking short city distances

Overview

Discover Chicago’s architectural gems on a private, personalized tour through downtown’s iconic skyscrapers and historic landmarks. Perfect for architecture lovers and curious travelers seeking an insider’s view of the city’s skyline.

City Tour
Food Tour
History Tour
Chicago, Illinois

Private Chicago Architecture & Highlights Tour

From $276 | 2.5 hours| Experience America's most architecturally striking city!

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Adventure Photos

Private Chicago Architecture & Highlights Tour photo 1

About This Adventure

Highlights

  • Experience the beauty of some of Chicago’s most iconic architecture.
  • Learn how Chicago got its famous nicknames: “Second City” and “Windy City.”
  • Gaze upon the beauty of the Chicago skyline as you walk through the Loop, along the Riverwalk, and down Michigan Avenue.
  • Enjoy a surprise local treat with your guide!
  • Marvel at the iconic bean sculpture in Millennium Park to round off the tour.

Inclusions: Local, English-speaking guide and a surprise local treat. Exclusions: Additional food and drink, souvenirs, tips and gratuities for the guide.


Summary

Welcome to Chicago! Here in the Windy City, there’s got outstanding architecture, inspiring public art, and a fabulous downtown district. Come along with a local guide to check out some of the Must-See spots in downtown Chicago. You certainly can’t miss the soaring architecture that Chicago is famous for (you’ll be surrounded by it!) - and you’ll learn about the history of some of Chicago’s most well-known buildings. In addition to enjoying views of the Chicago River (if the weather is good, you’ll be able to walk along it), plus a delicious local treat! And, of course, your guide will show off some local-favorite hidden gems along the way too! You’ll really get a feel for what makes Chicago one-of-a-kind on this tour.

Adventure Tips

Wear comfortable walking shoes

The tour involves walking through city streets, so durable footwear will keep you comfortable throughout.

Bring a camera or smartphone

Chicago’s architectural details are stunning—capture your favorite moments for memory and inspiration.

Check weather forecasts

Tours proceed rain or shine, so dress appropriately to enjoy the experience fully.

Arrive early

Plan to reach the meeting point at least 10 minutes before start time to ensure a prompt departure.

Local Insights

Wildlife

  • Urban birds like peregrine falcons
  • Squirrels often seen along the riverwalk

History

Chicago’s architecture rose dramatically after the Great Fire of 1871, igniting a building boom that shaped modern skyscraper design.

Conservation

Chicago actively promotes sustainable architecture and green building practices, highlighted in several new downtown developments to reduce environmental impact.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Essential for navigating city streets comfortably during the tour.

Weather-appropriate jacket or umbrella

Essential

spring specific

Sunglasses and sunscreen

Protect yourself during outdoor portions of the tour on sunny days.

summer specific

Light scarf or layering piece

Helpful for cooler temperatures in autumn.

fall specific