Layover in Chicago

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I have a 9 hour layover in Chicago this week. I’ve never been but is there anything worth leaving the airport for?

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Willis (Sears) Tower was the world’s tallest building for a time and has great views. Art Institute of Chicago and Field Museum (natural history) are both great. Cubs game if the stars align.

I know you can easily take the metro from ORD on the cheap. Pretty sure you can from MDW too.

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I did consider a Cubs game and they are playing at home that day.

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This is possible, but budget anywhere between 1-1.5 hours. Would be slightly more work to take the Blue Line to Addison or Belmont and hop on a bus over to Wrigley. To make things simpler, could just ride share or taxi, but there is a lot of construction south on the Kennedy and it doesn't get any easier going east once you exit.

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Is the downtown area worth walking through?

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If you've never been, might as well - can take in some of the usual tourist sites around The Loop (i.e. Millennium Park, Art Institute, Grant Park Willis Tower, River Walk, etc.). You could even stretch yourself into Magnificent Mile and walk Michigan. This is an easy route on the Blue Line and you can get off anywhere between Clark/Lake and Monroe, depending what you do first. I get off at Clark/Lake for work, which is where most of the Blue Line passengers exit, too. Just the easiest for anyone working in The Loop or across the river in River North.

ETA: Mentioned in my section about Wrigley, but please check travel time on Google Maps if you head downtown. There is southbound construction on the Kennedy that has made rush hour hell on earth - drops to two lanes and you're much better off taking the Blue Line at that point.

O'Hare or Midway?

ORD is a solid 30-45 minute commute via Uber to downtown.

I would check out Willis Tower, see Navy Pier, and eat at Lou Malnati's.

Chicago is highly accessible from both airports via CTA (trains). ORD- Blue line. MDW- Orange line. These will get you to The Loop downtown in 30-45 mins. From there, you can get wherever you want to go.

System Map

Downtown Map