Chicago Sightseeing: Loop to Lakefront

Chicago’s skyline rewards two very different vantage points, and its street-level sights cluster tightly enough to see most of them on foot between stops. Here is how the pieces fit together.

Two observation decks, two views

Willis Tower Skydeck, at 233 S Wacker Dr in the West Loop, sits 1,353 feet up on the 103rd floor and includes The Ledge, four glass balconies cantilevering 4.3 feet out over Wacker Drive; general admission starts from $32. 360 CHICAGO, at 875 N Michigan Ave on the Magnificent Mile, sits lower at 1,030 feet on the 94th floor but looks directly out over Lake Michigan and Oak Street Beach, with its TILT platform tilting 30 degrees downward. Weekday admission runs $30, weekend $35. Compare Skydeck and 360 CHICAGO tickets on GetYourGuide . Check the live webcams at theskydeck.com before paying on an overcast day; lake fog can drop visibility to zero from either deck.

Navy Pier extends 3,300 feet into Lake Michigan and is free to walk, with the Centennial Wheel, Chicago Children’s Museum, and Chicago Shakespeare Theater along its length. Summer brings free fireworks on Wednesday and Saturday nights between Memorial Day and Labor Day. Book Centennial Wheel tickets on Viator .

Museum Campus

South of Grant Park, Museum Campus holds the Field Museum, home to Sue the T. rex, with basic admission at $30 for adults; Shedd Aquarium, where the Abbott Oceanarium houses beluga whales and sea otters, at $39.95 to $44.95 with a mandatory advance reservation; and Adler Planetarium, closed Tuesdays, with museum entry at $19. Details for all three are at fieldmuseum.org , sheddaquarium.org , and adlerplanetarium.org .

The Art Institute and Millennium Park

The Art Institute of Chicago at 111 S Michigan Ave houses American Gothic and the largest Impressionist collection outside Paris; it closes only on Tuesdays, open the rest of the week including Wednesdays. A few blocks north, Millennium Park is free and holds Anish Kapoor’s Cloud Gate sculpture, popularly called the Bean, along with the Jay Pritzker Pavilion.

Griffin Museum of Science and Industry

In Hyde Park, about 8 miles south of the Loop, the Griffin Museum of Science and Industry holds the U-505 submarine and a full-size Boeing 727, reachable by Metra Electric from Millennium Station in roughly 15 minutes. This is too far to fold into a downtown walking day; budget a separate half-day for it.

The Magnificent Mile

Michigan Avenue between the river and Oak Street runs a mile of flagship retail past historic landmarks including the 1869 Chicago Water Tower and the Wrigley Building.

The verdict: pick one observation deck rather than both, since the views overlap more than the price difference suggests, then use the money saved on a Museum Campus ticket. For a hotel within walking distance of Michigan Avenue, check rates on Booking.com , and see the attraction tours guide for the river cruises that connect several of these stops by water.