Many of the attractions in Chicago are a short taxi ride away from Union Station so if you have checked your luggage and don't have to deal with bags, there are a number of choices available depending on your interests. With 5 hours, you could see most of the Shedd Aquarium or at least some of the major attractions in the Field Museum (natural history). You could go to the Art Institute and see the portions of the exhibits that appeal to you most though you wouldn't have time to see everything as their collection is extensive. You could go to Millenium Park and simply relax a bit. There are a number of short tours by water that are offered either on the river or on Lake Michigan. You would catch those tours either at the Navy Pier or by Michigan Ave. as it crosses over the river. I don't know how many are in your party or the ages, but my grandsons loved the children's museum at Navy Pier with lots of interactive things to do which could help children burn off some of their energy so they are prepared for further travel. If you simply want to get a view of the city, the Sears Tower (name has changed now--don't remember what it is) is another option. There are lots of options. It just depends on what you are interested in. I would suggest getting a guide to Chicago, perhaps from your library, and reading about some of these things and maybe looking at a map to see which would be the most easily accessible. The ones I have mentioned should take no more than 10-15 minutes to get there by taxi from Union Station.
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