Chicago for first-time visitors
Willis Tower is the skyline view that reset what a skyscraper was allowed to be. The earliest of the picks for first-time visitors in Chicago opens at 07:00 and the latest closes at 02:00.
Chicago for first-timers, in numbers
- Picks on this page
- 24 places across 2 lists, led by Willis Tower, Franklin Center (Chicago), 900 North Michigan
- Posted hours
- 11 picks post hours earliest 07:00, latest 02:00; 1 open by 09:00, 5 past 21:00
Questions first-timers ask about Chicago
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Must-see
The Art Institute of Chicago, founded in 1879, holds the largest Impressionist collection outside France. Start in Gallery 240 with Seurat's 'A Sunday on La Grande Jatte.' General admission is $35, and the museum sits at the south edge of Millennium Park on Michigan Avenue, so Cloud Gate is a 5-minute walk from the exit.
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Best time to visit
September is our pick for Chicago, with early October a close second. Afternoons reach 24°C (75°F), the lake stays warm enough to swim, and architecture boat tours on the Chicago River run daily. Skip January and February: the wind off Lake Michigan makes -10°C feel far colder.
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Airport to city
Take the CTA Blue Line from O'Hare (ORD) to downtown Chicago. It costs $5, runs 24 hours a day, and reaches the Loop in about 45 minutes. From Midway (MDW), the Orange Line costs $2.50 and takes 25 minutes to the Loop. Both trains beat taxis on price and, during rush hour, on speed.
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How to get there
Chicago has two airports. O'Hare International (ORD), 27 km northwest of the Loop, handles most domestic and all long-haul flights on United and American. Midway (MDW), 16 km southwest, is Southwest Airlines territory. Nonstop from New York takes 2.5 hours at $120-250 round-trip. From London, 8.5 hours on BA or United at $600-900. Amtrak's Union Station connects 30+ US cities by rail.
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Getting around
The CTA L train is Chicago's transit backbone. Eight color-coded lines cover most visitor destinations, and the Blue and Red lines run 24 hours. A Ventra card costs $5 and loads with pay-per-ride at $2.50 per train trip. Uber and Lyft fill the gaps after dark and for neighborhoods the L misses.
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Curated for first-timers
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Must-see attractions
Chicago's great attractions are built things, and the dates read like a timeline: Holy Name Cathedral from 1874, Our Lady of Sorrows Basilica (out at 3121 West Jackson Boulevard) from the same year, the Chicago Theatre from 1921, Buckingham Fountain from 1927, the Civic Opera House from 1929, Willis Tower from 1971, the Harris Theater from 2003, and Cloud Gate from 2004. Several carry formal protection. The fountain, the theatre and Navy Pier are all Chicago Landmarks, and the cathedral is listed on the National Register of Historic Places. This list is for the visitor who wants the city's real architecture and public spaces, and who will skip the souvenir circuit. We've mixed the obvious names with places of worship that most itineraries leave out, including Mosque Maryam on South Stony Island Avenue. Go in any order, but do go to all twelve.
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Best restaurants
Chicago's Loop is not where most food writers send you, and that is exactly the reason to eat here. The dozen rooms below sit within a few blocks of one another between Adams, Monroe, Madison and Jackson, close enough that you could walk the whole list in a lunch hour and still argue about which door to open first. The mix is honest to what the neighborhood is: a century-old German dining room, two deep-dish counters that made the city's name, a hotel dining room built for people who want breakfast at 07:00, a couple of quick Middle Eastern and Asian counters wired for the lunch rush, and a handful of Italian rooms that hold the evening after the offices empty. Skip the tourist mile on Michigan and eat in the working Loop instead; the food is better, the addresses are easier to find, and the hours line up with a real day of walking. Every claim below (every street number, every closing time, every cuisine) is cited to a verifiable source. Use the phone numbers to book; use the addresses to walk.
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