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I am flying into Chicago tomorrow and have a 5.5 hour layover. I am arriving from Holland and flying to Canada afterwards. Is this possible?

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When asking questions such as this, it is helpful to include your airline, approximate time of arrival, what nationality your passport is, and whether you have any frequent flyer elite status. –  choster Oct 7 '13 at 13:41
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Legally, yes. I certainly wouldn't go anywhere other than right near the airport with a 5.5 hour layover, though! –  Loren Pechtel Oct 8 '13 at 0:31
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Most US airports have no concept of "transit" and no "airside" where you can make your connection. You land, clear US customs, and then can go wherever you like, whether that's just over to another terminal to catch your plane, or out into the city to explore. So if you have the paperwork to enable the connection, then you almost certainly have the paperwork to go visit Chicago.

There are 4 terminals. United uses mostly Terminal 1 and a little Terminal 2. When figuring out how much time you have, you'll need to include not just clearing US immigration when you land, but clearing security when you go back airside, and possibly some time for moving between terminals. As well, flights into Chicago are often delayed. I think that means in the end you have an awkward layover that doesn't really give you time to leave the building, but is really boring to spend in the airport.

That said, if you're the adventurous type who would love to grab a train or a taxi to a single high-profile attraction, take a look at the tourist pages and see if the timing can work out. You might get two hours somewhere if you try hard.

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I agree with you. As with a lot of major cities, the airport is pretty far away from most of the downtown attractions. I would budget about an hour each way for the Blue Line to get downtown. Add to that time for security and getting to the gate early and whatnot (going to Canada means an international flight), and you're not left with much time at all. –  Kris Harper Oct 7 '13 at 13:27
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I did it a month ago, but I had 9 hours between my flights. And I was lucky because I decided to return to the airport earlier than necessary: the CTA derailled and we had to take a bus to return to the O'Hare.

You'll spend almost one hour to go downtown, and another hour to return, so you'll have some 3 free hours. I went to the the Chicago Beans (not the real name!) and liked it very much.

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Doing it with 9 hours is very different than doing it with 5.5 hours. –  Loren Pechtel Oct 8 '13 at 0:32
    
@LorenPechtel : yes... that`s why I just told about the Chicago Beans (a very beautiful monument) and not the whole sightseeing I made. –  woliveirajr Oct 8 '13 at 11:41
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It doesn't leave three hours at all. Clearing US immigration usually takes at least half an hour can easily be an hour or more. You need to be back at the airport at least an hour and a half before the scheduled departure time. So we're actually talking between half an hour and an hour and a half of sightseeing. –  David Richerby Apr 24 at 20:45
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Getting through immigration usually takes at least half an hour and can often take an hour or more. Getting from O'Hare to downtown is another hour; getting back is yet another hour. You need to be back at O'Hare an hour and a half before your outgoing flight. That only leaves an hour to an hour and a half of your layover for actual sight-seeing.

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