Chicago Sightseeing at Full Speed

Chicago rewards visitors who go up first and walk second. Get the skyline from 1,000-plus feet, then come back down and cover the same ground on foot along the river and the lake.

Pick your observation deck

Willis Tower Skydeck sits at 1,353 feet on the 103rd floor, with The Ledge’s glass balconies cantilevering 4.3 feet out over Wacker Drive for the vertigo photo. General admission starts at $32, open until 10:00 pm March through September. Across town, 360 CHICAGO occupies the 94th floor of the former John Hancock Center at 1,030 feet, lower, but with a lake-facing angle that actually puts the Willis Tower into your skyline shot, plus the tilting glass TILT platform for another version of the vertigo photo. Weekday admission is $30, weekend $35. Book Skydeck tickets ahead through GetYourGuide to skip the line on a busy afternoon.

Museum Campus in one afternoon

Three major institutions sit within walking distance of each other south of Grant Park. The Field Museum ($30 basic admission) holds Sue, the most complete T. rex skeleton ever found. Shedd Aquarium ($39.95 to $44.95, timed reservation mandatory) runs the Abbott Oceanarium with beluga whales, dolphins, and sea otters. Adler Planetarium ($19 entry, closed Tuesdays) rounds it out with sky shows. Budget a full afternoon if you want to do all three without rushing. Book a Museum Campus combo ticket on Viator if you want the Shedd reservation locked in alongside Field Museum entry.

The free stuff between the paid stuff

The Chicago Riverwalk runs 1.25 free miles along the river’s south bank, split into six distinct sections from The Marina to The Boardwalk, open 6:00 am to 11:00 pm. Millennium Park, also free and open the same hours, holds Cloud Gate and the Crown Fountain. The Magnificent Mile stretches one mile of Michigan Avenue between the river and Oak Street, lined with the 1869 Chicago Water Tower and flagship retail. None of this costs anything beyond a transit fare to get there.

Navy Pier itself is free to walk, a 3,300-foot pier jutting into Lake Michigan. The Centennial Wheel runs $19 to $21 for adults, and free fireworks go off Wednesday and Saturday nights from Memorial Day through Labor Day. Check the fireworks calendar and current Navy Pier hours before you plan an evening visit.

Weather is the wildcard

Lake fog and low cloud ceilings can drop visibility at both observation decks to zero on an overcast day; check the live webcams on theskydeck.com or 360chicago.com before you pay for a ticket if the forecast looks grey.

Getting between it all

The Loop’s Brown, Orange, Pink, and Purple lines connect Skydeck to Museum Campus and the river in a handful of stops, all at the standard $2.75 fare. If you’d rather cover the same ground by boat first, see the Chicago attraction tours guide for the river cruise operators and their docks.