Best of Chicago Trip

Starting Price $700 per person
Trip Duration 5 Days
Availibility All Year
Activity Level Medium level of fitness
  • Explore Navy Pier
  • Visit Millennium Park and the Cloud Gate
  • Chicago Architecture Boat Tour
  • Visit the Art Institute
  • Live Jazz Performance
  • Visit Shedd Aquarium
  • Free time at the Water Tower Place
  • Tour Wrigley Field
  • See a Broadway Style musical performance
  • Gangster Tour of Chicago
  • John Hancock Observatory
  • Free time on Michigan Ave
  • Live Improv Show
  • Go to a Cubs Baseball Game
What To Expect

Catch a glimpse of Chicago’s eminent architecture, explore the city’s extensive collection of art galleries and museums and catch a ball game, theatre performance or comedy show.

Educational Benefits

Evolve Tours Chicago Trips can be tailored to your class curriculum. Contact us today for more information on how to customize the perfect trip.


All Evolve Tours itineraries are completely customizable for your groups desires and needs.

Daily Itinerary

Day 1 - Travel to Chicago

We will explore the Navy Pier along Lake Michigan upon arrival in Chicago before going to dinner as a group.

Day 2 - Welcome to Chicago

On a Millennium Park tour, we’ll visit the Cloud Gate and the Crown Fountain. Next we’ll get a unique look at Chicago Architecture on a river cruise. Now, we’re off for a self-guided Tour of the Art Institute – a world-class art museum. This evening we’ll have dinner at a live jazz performance!

Day 3 - Explore Chicago

Visit the Shedd Aquarium this morning. It contains over 25,000 fish and the adjacent Oceanarium has whales, dolphins, sea otters, harbor seals and penguins for you to see! Tour Wrigley Field in the afternoon. We’ll visit the press box, clubhouses, and/or dugouts and we’ll even get a chance to step onto the field! Attend a live Cubs baseball game in the evening.

Day 4 - Another full day of Chi-Town

Today a local guide playing the part of a 1920’s gangster leads the group through a historical tour of Chicago. We’ll check out the John Hancock Observatory and Skywalk. Chicago looks very different from 1,000 ft in the sky! Explore Michigan Avenue next and enjoy a live improv comedy show after dinner as a group.

Day 5 - Homeward Bound

Enjoy a final morning in Chicago, depending on travel schedule. Say goodbye to Chicago after a great trip!

  • Airfare
    Roundtrip group airfare to Chicago, depending on departure city
  • Coach Bus
    Private coach bus for duration of tour, equipped with A/C, T.V & DVD players, on-board washroom
  • Hotel
    Centrally located, student friendly, 3 * minimum, acclaimed hotels

Daily breakfasts and dinners included in tour. Meals at locally owned and delicious restaurants.

Meet Our Leaders
Kate Lindner
Did you know?

Four States are visible from the top of the Willis Tower: Indiana, Illinois, Michigan, and Wisconsin.

Places You’ll Visit

Navy Pier

The pier dates back to 1916.

Millennium Park

Evolve led games and tour of Chicago's premier park.

Art Institute

Featuring a collection of Impressionist and Post-Impressionist art.

Shedd Aquarium

World class aquarium.

Wrigley Field

One of the most famous and storied baseball stadiums.

John Hancock Observatory

360° view of the city.