Arrive in Chicago
Fly in and check into your hotel in the Loop or Near North. First evening on your own — Chicago's restaurant scene is extraordinary.
Chicago is one of the great American cities, and it rewards the kind of visit where you actually stay long enough to understand it. The architecture river cruise is still the best introduction to any American city — an hour on the water with a docent who explains how the city was built, burned down, and built again better. The Art Institute. Millennium Park. The food. Five days is the right amount of time.
Tour Highlights
- Architecture River Cruise — the essential Chicago experience
- The Art Institute of Chicago — one of the greatest collections in the world
- Millennium Park and Cloud Gate
- The 360 Chicago or Willis Tower Skydeck
- Chicago-style deep dish pizza and the Chicago hot dog
- The Magnificent Mile and the lakefront
What to Expect
Architecture & the River
Morning architecture river cruise. Afternoon free to explore the Magnificent Mile or the lakefront.
The Art Institute
One of the world's great art museums. Afternoon at Millennium Park.
Neighborhoods
Chicago's neighborhoods are half the reason to visit. Wicker Park, Andersonville, Pilsen, or the Gold Coast — your tour director will help you choose.
Return Home
Morning at leisure before flying home.
What's Included
Included
- Roundtrip airfare
- 4 nights hotel
- Architecture River Cruise
- Art Institute of Chicago admission
- Professional tour director
Not Included
- Meals
- Personal purchases
- Travel insurance (recommended)
Frequently Asked Questions
What is the weather like in early September in Chicago?
Early September is one of Chicago's best months — typically 70s, low humidity, and the lake is actually warm enough to appreciate.
Is Chicago walkable?
The Loop and Near North are extremely walkable. The architecture and the lakefront are best experienced on foot.