Adventure Collective
Explore Chicago in a Day: The Ultimate Urban Adventure - Chicago

Explore Chicago in a Day: The Ultimate Urban Adventure

Chicagomoderate

Difficulty

moderate

Duration

6–8 hours

Fitness Level

Moderate fitness level needed; able to walk several miles with some standing

Overview

Discover Chicago’s iconic skyline, vibrant neighborhoods, and famous eats in just one day with this comprehensive urban tour. Experience the city’s top landmarks and cultural highlights all in a single, memorable adventure.

City Tour
Food Tour
History Tour
Chicago, Illinois

Chicago in a Day

From $99 | 5 hours | An epic tour of some of the city’s greatest hits!

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Adventure Photos

Chicago in a Day photo 1

About This Adventure

Highlights

  • Take in Chicago’s breathtaking art and architecture, including The Bean and the beautiful historic Chicago Theatre
  • Take a stroll along the Chicago Riverwalk and Michigan Avenue to catch some picturesque views of the city skyline.
  • Enjoy immigrant-inspired cuisine from generations-owned shops in the lively Chicago Loop neighborhood
  • Get to know the history, fresh ingredients, and locally sourced beef behind such iconic staples like the Chicago deep-dish pizza
  • Hear stories from your local guide about Chicago’s evolution and how food played a significant part in its growth.

Inclusions: Local guide and a variety of food samples (such as a slice of deep dish pizza, a sample of local street food, a sweet treat, and a bite of an additional Chicago classic). Food options and portion sizes vary - total amount of food equals a full meal.

**Exclusions:**Additional food and drink, souvenirs, tips and gratuities for the guide.


Summary

Get the whole Chicago experience combining our Chicago Architecture & Highlights Tour and Chicago Food Tour: Deep Roots to Deep Dish!

Our two-part tour begins by exploring the heart of downtown Chicago - with its iconic architecture, both old and new, views of the Chicago River, picturesque Millenium Park, and bustling city avenues (plus, a couple tasty local treats along the way).

From there, we’ll hit the Central Loop, where locals go to grab their favorite foods, day and night. Try the best of Chicago fare and get to know the history and how-tos (and how-not-tos) behind iconic street and comfort food staples - from the infamous deep-dish pizza to sandwiches to a loaded hot dog!

Your local guide will entertain with fascinating stories and the everyday immigrant chefs and vendors responsible for Chicago’s eclectic food scene. By the end of the tour, you’ll have a deep appreciation for both the evolution of this excellent city and the role food has played in the lives of all Chicagoans!

Adventure Tips

Wear comfortable walking shoes

This tour covers several miles on foot through urban streets and riverwalks, so sturdy shoes will keep you comfortable all day.

Bring a refillable water bottle

Stay hydrated as you explore outdoor and indoor city spots, especially during warmer months.

Check the weather forecast

Chicago’s weather can change quickly—dress in layers to stay comfortable throughout the day.

Use public transit to get there

Parking downtown can be expensive and scarce; take advantage of Chicago’s efficient train and bus system.

Local Insights

Wildlife

  • Urban Red-tailed Hawks
  • Lake Michigan’s resident gulls

History

Chicago’s rise as a railroad hub in the 19th century set the stage for its architectural boom and cultural prominence.

Conservation

Efforts to preserve the Chicago River and Lake Michigan waterfronts have improved water quality and enhanced urban green spaces for recreation.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Supports long periods of walking on pavement and uneven city surfaces.

Layered clothing

Essential

Adapt easily to Chicago’s variable weather throughout the day.

Sunscreen

Essential

spring specific

Water bottle

Essential

Keeps you hydrated while walking around the city.

summer specific