The Chicago collection
Big city.
Better details.
Three days of museums, river views, deep dish, and a Magnificent Mile stay. Here’s how we put it all together.
Start with the 3-day itinerary
01 · Before you book
Build your Chicago trip
Start with the itinerary, then decide which tickets deserve a place in it.
3 days in Chicago: our complete first-time itinerary
A firsthand Chicago plan built around the Magnificent Mile, an architecture cruise, CityPASS museums, deep dish, two observation decks, and the routes worth walking—or riding.
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Is Chicago CityPASS worth it? Our honest five-attraction review
We used the standard Chicago CityPASS for Shedd, Skydeck, Field, 360 CHICAGO, and Griffin. Here is what the two-pass total bought us, what we saved, and which attraction won.
Read the storyBest Chicago attractions ranked: our honest six-stop scorecard
We rated Griffin, Shedd, Field, Skydeck, an architecture cruise, and 360 CHICAGO after visiting all six. Here is what each score means—and which one fits your trip.
Read the story02 · Make the days count
Choose your days out
Museums, skyline views, and the river—with the timing lessons from our visits.
Griffin Museum of Science and Industry review: is it worth a full day?
We arrived at opening, left around 2 p.m., and rated Griffin 9 out of 10. Here is what made it our favorite CityPASS attraction—and why the crowds kept it from a perfect score.
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Can you visit Shedd Aquarium and the Field Museum in one day?
Yes—if you want a highlights day. We started at Shedd at 10 a.m., walked to the Field Museum, and finished around 2–3 p.m. without the day feeling rushed.
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360 CHICAGO vs. Skydeck: which observation deck is better?
We visited both with Chicago CityPASS—360 CHICAGO at sunset and Skydeck at midday. Here is why the calmer Ledge experience won, 8 out of 10 to 6.
Read the storyChicago Line Cruises review: is the 90-minute architecture tour worth it?
A firsthand review of Chicago Line’s Original Architecture Cruise—including the exceptional guide, onboard drinks, summer heat, and the shorter CityPASS alternative.
Read the story03 · Between the sights
A place to stay. A table worth finding.
Our Magnificent Mile base and a proper Chicago pizza stop.
InterContinental Chicago review: is the Executive Tower worth it?
A firsthand three-night review of the Executive Tower King—including the standout bathroom, historic pool, $100 Amex credit, high-set window, and excellent Magnificent Mile location.
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Giordano’s stuffed deep dish review: the Chicago pizza you have to try
A firsthand look at Giordano’s towering stuffed pizza, why it is different from ordinary deep dish, and how to plan for the famous 45-minute bake.
Read the storyThe decisions we’d take with us
Our Chicago
shortlist.
Scores reflect our July visits, including the weather and crowds we experienced.
See all six ratings and the reasonsGriffin Museum
Give the tornado, U-505, trains, and aircraft the time they deserve.
Skydeck Chicago
A calmer midday visit and The Ledge made the difference.
The architecture cruise
Excellent guide; July heat made 90 minutes feel long. Consider a shorter cruise on a hot day.