Chicago: Worth It? An Honest Look
Chicago has a chip on its shoulder about New York and Los Angeles, and it’s earned. The architecture is more consistently interesting than New York’s skyline, block for block. The food is more varied and less precious than LA’s celebrity-chef circuit. The blues, house and jazz traditions here are native, not imported for a festival circuit. And the city is genuinely cheaper than either coast, a fact locals mention constantly because it happens to be true. Verdict: worth it, and the best of it doesn’t cost a dime.
| Chicago at a glance | |
|---|---|
| Price to see the skyline | Free (Riverwalk, Millennium Park) |
| Price to see it from above | $30-32 (360 CHICAGO weekday / Willis Tower Skydeck) |
| Time needed | 3-4 days downtown, a week with neighborhoods |
| Booking lead | River cruise and Skydeck: book ahead for summer weekends |
The one paid thing worth doing here
If you do one paid activity in Chicago, book the Chicago Architecture Center river cruise , run by the nonprofit behind architecture.org . Ninety minutes on the Chicago River with docent narration covering the Tribune Tower, the Wrigley Building, Mies van der Rohe’s glass towers and the “Corncob” Marina City buildings. USA Today readers voted it the country’s best boat tour in 2025, and after doing it, the observation-deck argument mostly answers itself: you’ve already seen the skyline from the best angle available.
What’s actually free
Millennium Park and Cloud Gate , the sculpture everyone calls the Bean, sit at the center of the Loop and cost nothing. The Chicago Riverwalk runs along the south bank connecting the Loop, Michigan Avenue and Navy Pier on foot, also free. Lincoln Park Zoo is free 365 days a year, no ticket required at all, which is rarer than it sounds for a zoo this size.
What’s worth paying for
The Art Institute of Chicago runs $32 for adults, $26 for seniors and students, and holds one of the strongest Impressionist collections outside France. The Willis Tower Skydeck (the tower carried the Sears name until 2009) starts at $32; 360 CHICAGO on Michigan Avenue runs $30 on weekdays and $35 on weekends and keeps the Willis Tower itself in your photos, which the Skydeck’s own deck can’t manage. Pick one, based on price that week, not both.
Food, the local argument
Deep-dish pizza, cheese first, then toppings, then sauce on top, is the export version, at Lou Malnati’s and Giordano’s. Tavern-style, cracker-thin and cut into squares, is what most Chicagoans actually order on a weeknight, at places like Vito & Nick’s. Order deep dish once, with a table of people to share it, and spend the rest of the trip eating the thin-crust version instead.
Getting around
The CTA’s rail fare is $2.75 and bus fare is $2.50 as of the February 2026 restructuring, tapped with a Ventra card or a contactless bank card. From O’Hare, the Blue Line runs 24 hours a day, the only Chicago airport rail line that does. From Midway, the Orange Line is faster when it’s running but still has a nightly gap, so check current CTA schedules before planning a late arrival there.
Where to stay
Base yourself in the Loop or River North: walking distance to Millennium Park, the Art Institute and the river cruise docks, with River North carrying the denser restaurant and bar scene. Check Loop and River North rates on Booking.com rather than trusting a listing that claims to be “near Chicago” from 25 minutes away.
Is Chicago worth a repeat visit?
Yes, more than most American cities its size. A first trip covers downtown; a second trip is where Pilsen’s murals, Hyde Park’s Obama Presidential Center (opened 19 June 2026) and the South Side’s Pullman National Historical Park earn their place. For the full spine, see our Chicago guide and the 2-day through 7-day itineraries. For day trips, our Chicago, Illinois and Chicago, USA guides cover Starved Rock and Milwaukee respectively, both outside the city’s own case for itself.