Tap to ride. The L is $2.50 and a bus $2.25. Tap a contactless bank card or phone at the turnstile and you pay the Ventra fare with the same free transfers, up to two more rides within two hours. A 1-day pass is $5 and a 7-day $20; a plastic Ventra card costs $5, so skip it unless you want a pass.
From both airports. From O’Hare the Blue Line runs all night and reaches the Loop in 40 to 45 minutes; boarding there costs $5 unless you hold a pass. From Midway the Orange Line takes 20 to 25 minutes for $2.50 and does not run overnight.
The boat. Book the Chicago Architecture Center river cruise aboard Chicago’s First Lady: 90 minutes with a docent the Center trained, from the dock at 112 East Wacker on the southeast corner of the Michigan Avenue bridge. The 2026 season runs March 15 to November 22, the fare is around $57, summer weekends sell out, and you board 30 minutes before. Other companies run cheaper narrated cruises; this is the one about the buildings.
The museums. The Art Institute is $32 for visitors, closed Tuesday, open to 8 p.m. on Thursday; under 14s and Chicago teens are free. Its free Thursday evenings (third Thursdays from April, every Thursday mid-June to mid-September in 2026) are for Illinois residents with ID. The Field is free to Illinois residents on Wednesdays in 2026 and from $30 for everyone else on a dated ticket; the Shedd gives residents free Tuesday evenings and sells timed entry from about $39. For a visitor they change only the crowds: avoid the Field on a Wednesday.
Millennium Park. Free and open every day. Cloud Gate has been back in the open since June 2024; then Crown Fountain, which runs in the warm months, and the Pritzker Pavilion’s free summer concerts. The ice rink opens in winter.
Pizza. Deep dish takes 35 to 45 minutes to bake, so order as you sit down, and one slice is a meal. Tavern-style, thin, crisp and cut in squares, is what Chicagoans order on a weeknight.
Tipping. 18 to 20 percent at a table, a dollar or two a drink at the bar. Restaurant meals carry about 10.75 percent tax, a little more in the downtown zone, and it is added to the menu price before the tip.
On the day. Bring a layer in July and a hat and gloves from November; the wind off the lake is the weather. The Pedway under the Loop keeps you indoors between the L and the museums. Waystop’s hours check will catch the Art Institute placed on a Tuesday.