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Photo: No machine-readable author provided. Abrahami assumed (based on copyright claims)., CC BY-SA 2.5 via Wikimedia Commons
Known for their inventive, acrobatic shows; their repertory production of "Lookingglass Alice" is a knock-out. It's worth peeking inside even if you don't plan to see a show, though, to check out the insides of the old Pumping Station; unlike the Water Tower, its more famous sibling across the street, there's some interesting old machinery to see.
Lookingglass Theatre Company is a non-profit theater company located in Chicago, Illinois.
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In 1871, when Mrs. O'Leary's cow kicked over the lantern in her barn — or was framed for the act, depending on who you ask — the Gothic Revival spires of Water Tower were only two years old. Today, along with the Pumping Station on the other side of the street, the Water Tower is the last, dream-like symbol of the Old Chicago that disappeared in the Fire. Surrounded by hotels and colossal department stores, it's also the icon of the new city that arose. At night, the Water Tower is lit from within, and it's a memorable sight. Inside, the vintage machinery is long gone (along with the water), and the plain interior is occasionally used as a gallery space.
Chicago Red Line
Right next to the Water Tower, LUMA is best known for its exhibits on sacred art and architecture, but it occasionally veers into modern art as well, such as an installation of Andy Warhol's silver balloons.
A Gothic Revival church built in 1912 provides a contrast to the surrounding bustle.
Hancock Observatory
360-degree view from the 94th floor. Not quite as high as the Sears Tower Skydeck, but with a better view, and from January to March, an ice-skating rink! For drinks, see the Signature Room below.
Contemporary art from around the world. The MCA has a great location and plenty of financial backing, but it's still fighting for recognition in the museum world; while not an upper-tier institution as yet, that has resulted in some interesting exhibitions. There isn't much of a permanent collection, so check what's on before you go. Also, Marisol is the museums' Latin- inspired all day café, that's quickly become a draw in a part of Streeterville, not exactly known for its cuisine.
Adorning the first floor are decorative arts from the collection of the museum's namesake, Richard H. Driehaus, with plenty of Tiffany stained glass. But it's the restored 1883 mansion itself that garners glowing reviews; inside are 17 different types of marble, hand-painted ceilings, carved exotic wood wainscoting and other marks of superior 19th-century craftsmanship. If you're interested in historic architecture and interior design, this is still a hidden gem without crowds.