Skyline View from Adler Planetarium Pier
Things To Do
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You won't need to pay a cent. As an architectural mecca for American architects, Chicago's skyline is one of the greatest this side of the world. From this angle, you really see the widest angle of the skyline. On a calm evening, the skyline reflects magnificently off Lake Michigan. You'll see a handful of tourists, but it's pretty sparse.
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Montrose Harbor
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This yahct offers some nice views of the Chicago skyline. The tiny harbor is also near Montrose Beach and the Lakefront Trail (a beautiful scenic trail by Lake Michigan).
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Half Acre Beer Company
Things To Do
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It's the best brewery tour you can find. Once a week: 11am every Saturday, they give a full showing. It's limited so plan to be in line. 2hr tour that goes into everything: brewing, ingredients, buying, building, and the business itself. Other tours may show you what they do. Half Acre will tell you how to do it yourself. 3-4 full pint samples too.
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City Winery Chicago Riverwalk
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You should go for the great view of the river and great wine. The Riverwalk has been newly renovated so it still has the "new and shinny" feel. You can come here for a meal or just for drinks. I would recommend going early-ish to be the crowd since the place has become very popular
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Chicago French Market
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For groceries you can find fresh produce, meats, fish, bread, and cheese. There is a nice selection for breakfast with a couple cafes as well as a good crepe restaurant with sweet and savory crepes. The savory crepes kind of look like a burrito. And sushi, soups, grilled food, and many more!
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Christkindlmarket
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While the Chicago winters can be bitter, it's a great way to get outside and make the best of all the holiday festivities. There are plenty of great treats and foods to try, lots of quaint shops for cute trinkets, and of course the giant Christmas tree. Duck inside the hut for cover from the weather and enjoy some hot wine or a warm meal.
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Take the CTA Loop
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It's a cheap way to see the gorgeous architectural canyons of Chicago's downtown. The 'L' is elevated above the street and wraps in a loop around the commercial core of Chicago, going between the historical skyscrapers of its skyline. Take The Loop all the way through and enjoy the views as you zip between buildings and over rivers.
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Chicago Architecture Foundation River Cruise
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This tour gives travelers a great background of the history of the city and what makes it special. Obviously architecture and history buffs will love it but even kids will enjoy being on a boat and gazing at the skyscrapers.
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Baha'i Temple
Things To Do
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It's the only Baha'i Temple in North America. It also looks more like something you'd find in Istanbul. If you're a fan of cultural juxtaposition, it doesn't get much better than this. Making a trip up to the much more tranquil nearby Evanston will also be a fantastic break from the hustle and bustle of the city.
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The Signature Lounge
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There is no fee to enter The Signature Lounge and the price of a drink is cheaper than a ticket to see the view at Willis Tower (no bar at the top of the Willis Skydeck). If you want to get the most of the Chicago skyline come to this lounge for sure.
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State Street Shopping
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Even if you are just window shopping this is the place go in Chicago. The shops are a few blocks to Millennium Park and Maggie Daily Park so you could plan a family trip and end with the shopping and bring home your goods as well play in the park. You get the full city experience!
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chicago outfit roller derby - windy city field house
Sights
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You should visit for the entertainment. The ladies are totally bad ass. You'll see a bunch of tattoos and notice groups of family "cheerleaders". The location is out of the city center but it is worth to quench your curiosity
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Alfred Caldwell Lily Pool
Sights
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Anyone into landscape architecture or the Prairie school of architecture will appreciate Caldwell's design, and flower and plant lovers will enjoy the flora. It has a long history too - built in 1889, renovated in 1938, and restored in 2002. Visit the pond to escape the heat and crowds of people on a summer day!
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Maggie Daley Climbing Walls
Things To Do
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You should visit for the view and the outdoor climbing experience. This is a good place to bring kids and family groups. If you plan to go as a group and will be renting equipment make sure to book it ahead of time.
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Shoreline Sightseeing - Michigan Ave.
Things To Do
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You should do the tour because you will be able to easily see a lot of the city in 72 minutes. The Chicago River has recently become revived and is very active! The city had once forgotten the beauty of the river but has now added parks and cafes along the river.
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