How many days are enough for Chicago?+
3 days will cover the architecture, 2 major museums, the lake and baseball. 2 days is enough for downtown and a river cruise. Chicago pairs well with New York or with a Route 66 road trip, which starts here on Adams Street.
Is Chicago dangerous?+
The reputation comes from statistics in a handful of neighbourhoods on the south and west sides that tourists never reach. The Loop, River North, Lincoln Park, West Loop and Lakeview are safe even in the evening and full of people. On the L at night, stick to the first car near the driver, and avoid the southern ends of the lines after dark.
Which boat cruise is best?+
For architecture, the Chicago Architecture Center, departing from Michigan Avenue by the bridge — guides are trained volunteers and the commentary is substantive. Boats from Navy Pier are cheaper and combine the lake with the river, but the commentary is more entertainment-focused. Both last 1.5 hours.
Is the Chicago CityPASS worth it?+
If you want the Field Museum, Shedd Aquarium, Skydeck and one more attraction, you'll save roughly a third. If you're only visiting the Art Institute and taking a cruise, buy tickets separately. Plenty is free: Millennium Park, Lincoln Park Zoo, the Riverwalk and the beaches.
Where can you swim in Chicago?+
In the lake, from June to early September, when the water is 18–22°C. The closest beaches to downtown are Oak Street and North Avenue, both with lifeguards and skyline views. The water is fresh and clean, but strong winds bring waves and swimming bans.
What is the Windy City?+
The city's nickname, which locals explain as the wind off the lake, though historians say it originally mocked long-winded politicians. Either way, the wind is real — in winter it knocks the wind-chill down by 10 degrees, and it gusts between the skyscrapers of the Loop even in summer.
How do you get from O'Hare to downtown?+
Take the Blue Line, which runs nonstop straight from the airport terminal to the Loop in 45 minutes. A ticket from O'Hare costs more than one bought downtown, but the fare is otherwise the same. A taxi is more comfortable with luggage, but takes over an hour during rush hour.
What are prices like in Chicago?+
A downtown hotel costs USD 170–300 a night, deli food USD 10–15, a sit-down dinner around USD 60 per person. A beer costs USD 8. Compared with New York, you save mainly on accommodation — roughly a third.
