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What to do in Chicago, IL?

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I will be traveling to Chicago, IL for one day.  I will be traveling on a Monday and coming back on a Tuesday.  If you had about 6 hours in Chicago, IL - Downtown area, what would you see? or Do?


I'm looking for a cool/historic place to eat that is Chicago!  I am also looking to site see a place or two, but I won't have a lot of time.  



Thanks for the ideas!  



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I love the Field Museum the best.  The Shedd Aquarium is neat, but I've never been there when there haven't been long lines, even to pick up up pre-paid tickets.  I think the passageways that you have heard about are mostly in the Loop (which does not include the museums) ... not so much underground tunnels, but buildings that connect through their lower levels.  So, be prepared for cold weather ... and wind.  As far as food is concerned, Lou Malnati's is our family favorite, but Giordano's or Uno are excellent. 


If you want a museum off the beaten path, there is the Oriental Institute on the campus of the University of Chicago.  It is a quiet museum with lots of artifacts from the ancient civilizations of the near east.  If you are studying the Ancients, this place is really cool.  You can download some audio commentary onto your phone or ipod and listen along.  Not flashy enough for littles who need lots of stimulation, though.  Nearby is the Robie House - a Frank Lloyd Wright building that was featured in the book Chasing Vermeer by Blue Balliet.  And you can grab a quick bite to eat at Medici Bakery and take a stroll through Powell's bookstore. 

Edited by dirty ethel rackham
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What month will you be traveling? Will you be there during the day? Will you be with others and/or children? By downtown do you mean the Loop? There are several downtown areas of Chicago.


I'm going to assume you will be there soon -- so cold -- during the day by yourself and near the Loop. If that is the case, if you like art, go to the Art Institute of Chicago on Michigan Avenue between Jackson and Monroe. It's huge so you might want to check out what to see beforehand. Millenium Park is just north where you'll find the Crown Fountain, the Lurie Garden designed by Piet Oudolf and the Cloud Gate sculpture which is nicknamed "The Bean" because it looks like a shiny bean.







If you walk north on Michigan Avenue toward Oak Street, you'll see the old Water Tower and the Pumping Station, which both survived the fire of 1871, The Water Tower Place Mall and the John Hancock Building. The Hancock observatory, called the 360 Chicago, is open from 9 am to 11 pm. For a cheaper option, you could go to the Hancock's Signature Lounge on the 96th floor which opens at 11 am, I think. This is what I'd recommend. It's free to get in. If a clear day, views are spectacular. Chairs are comfy. Dress is nice jeans or better. It's a good place to take a break. Drinks are a bit pricey but not too bad. Lines to take the elevator up can get long around 6 pm, sometimes earlier. You get to the Lounge's elevator from the Hancock's Chestnut Street entrance.





If it's still lunch or early dinner, you can grab something to eat at L'Appetito in the Hancock's basement (lower level). I like their tostino sandwiches. Tasty and affordable.




Near the Hancock is the Museum of Contemporary Art. The best part is their gift store. Full of quirky, fun, and sometimes weird stuff.




As for where to eat, that depends on what you like and how much you want to spend. Tourists seem to go for deep dish pizza and Garrett's popcorn (two on Michigan Avenue). If you want to try something different, I can offer some suggestions.



Edited by MBM
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Perfect timing. I will be headed that way soon to see my soon graduate bootcamp. I'm in Texas and it will be so cold I wasn't sure what to do. Someone suggested the underground tunnel system that links the down town area. I will be watching this thread. 😉


The underground tunnel system is called the Pedway.



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I've lived in Chicago and the suburbs since 1990. There is so much to the city. It's very hard to see it all or even much of it! Anyway, since I am all done with my Thanksgiving prep work I'll toss out a few more ideas to consider:


South of the river in the Loop:


The Christkindlmarket is open now, if you're into that sort of thing. Many vendors come from Germany and Austria to sell ornaments, cuckoo clocks and food. My favorite is the bakery that sells strudel and lebkuchen. It's set up on Daley Plaza which is on Washington Street between Clark and Dearborn which is about four blocks west of Millenium Park. They're all major streets and safe but it's always a good idea to watch out for pickpockets. Lunch and after work/dinner times will be busy. You can also find a big Picasso sculpture at Daley Plaza.





North of the river near Michigan Avenue:


If it's lunchtime and you like cracker crust pizza, Pizzeria Via Stato on State Street in the front of the Embassy Suites Hotel has a lunch special -- small salad or soup, pizza or sandwich, and a small piece of chocolate pie -- for about $15. Ask for parmesan, too, because it's really good. This is our favorite pizza place in Chicago. Try to sit near a window. This small stretch of State Street offers a good view of the old Tree Studios, a mix of stores, businesses and artists' studios across the street.





About two blocks away at 43 E. Ohio is Eataly, a 3-story building full of Italian food/food courts. We usually munch on the focaccia sold on the 3rd floor. They have different kinds. On December 6th they will have a Mercatino di Natale, a holiday market, in the store that might be browse-worthy.





If you don't want pizza, XOCO has excellent food. It's at 449 N. Clark at Illinois Street and is one of Rick Bayless' restaurants. It's a good idea to study the menu beforehand. IMO, almost everything he makes is memorable, especially the pork. Lunch is usually very busy. If you see the line outside the door, then the line is very long because it runs inside as well from the entrance to the front of the restaurant. They're good at moving things along, though. Not open Monday or Sunday.




Just a bit north and west of the Hancock is Oak Street which has a bunch of little boutiques between Michigan and Rush Street. Bravco sells all kinds of travel-sized beauty things. So if any females will be with you, that's a good place for them. Cash only, I think.


Two blocks north of that on Rush Street is the Viagra Triangle, aka Mariano Park, where old guys show off their younger girlfriends and politicians rub elbows  after they've eaten at Gibson's. Fun to walk around in the evening.


Then, if you want to see some of the old brownstones, walk a few blocks north to Division, where the cheesy bar area is, continue north on State Street until you reach North Avenue which runs east-west. Across the street is the south end of Lincoln Park. Lincoln Park Zoo is north a few blocks. This time of year the zoo is pretty because it's lit up. It's also free. You could go to the zoo or continue east on North Avenue toward the lake. If you went through the underpass to the lake, you'd be near the public chess tables--no one will be playing -- too cold! Walk south on either quiet Astor Street or noisy Inner Lake Shore Drive. Once you reach E. Oak Street you could cross toward the lake on East Lake Shore Drive where the Drake Hotel is (you can go inside) and all the old, expensive co-ops. Then you could head back over to Michigan Avenue when you feel like it. Pearson would be a good street to do that.


Have fun! If you're lucky it won't be too snowy or cold.

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Since you don't have as much time, you may want to go to Willis Tower (used to be called Sears Tower) or the Hancock building, instead of the Field Museum. Willis has a glass observatory. You could eat in the Hancock if you wanted. Maybe you'd like Michael Jordan's restaurant? Maggianos is an excellent Italian restaurant. My favorite deep dish is Lou Malnati's.

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MBM's advice is spot on. I will just add this.


With just six hours, I would not bother with the Willis Tower, mostly because the lines will eat up all your available time. If you do choose to do the Willis Tower, definitely buy your tickets online, ahead of time. People who just show up end up awaiting in line for hours and hours.


I would also avoid going to one museum, much as I love the Chicago museums. They are massive, and you will not have time to truly soak it in. You won't see much of Chicago, and you won't get to linger the way you want to at the museum.


Personally, with that time frame, I would consider the following:


--Eat at a restaurant high up in the John Hancock building. You'll get mostly the same view as the Willis Tower, without the lines. 


--Consider a river tour. Dress warmly!


--Consider a walking tour or a Segway tour. Dress warmly!!!


--If you don't want to eat at the Hancock building, have pizza at Pizzeria Uno or Duo. I'd go with the Hancock building, though.


--Another possible destination is the Cultural Center, which has gorgeous mosaic tile and free art exhibits. It's nice to walk through and doesn't take a ton of time.


--Check to see if there are Christmas window displays at Macy's this year.


--Consider some of MBM's other suggestions.



And a final word of warning--dress warmly!!! It's always colder by the lake. The wind in Chicago is damp and bitter. When I go downtown, I often wear windproof rain pants as an added insulating layer. It's totally possible to spend time walking around downtown, even in winter, as there are lots of shops to duck into, but it's best to dress warmly.


A final recommendation--if you see Garrett's, stop in and get a combo bag of cheese and caramel popcorn. It's to die for. No where else in the country understands popcorn like Garrett's.

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  • 2 weeks later...

I'm back from Chicago!  Now that I am I can tell you why I went there.  If you know me, you know that I'm a Narcotics Detective on a Task Force.  We recently arrested several Cartel types.  We took off 38 kilos of Heroin with a street value of 2 million.  It was awesome.  I traveled to Chicago to take the evidence to our lab.  Ok, now back to Chicago.


It was my first time in Chicago and I was VERY impressed.  I didn't have a lot of time  I stayed at the Sheraton Hotel downtown.  The room was cool because I was told to get a corner room for the view.  I did and it was good advice.  The only thing I didn't like about where I stayed was there was no free breakfast.  I'm not sure if that's normal in Chicago or not but overall the hotel was fine.


I walked to the  Navy Pier to eat at Giordano's Pizza, which I heard had the best Chicago Style Pizza in Chicago.  It was good but with all the hype I was expecting better.  It was good pizza though and the Navy Pier was pretty cool  Great view of the lake.


I then tried to do a Boat Taxi Tour but they no longer did them because it was out of season.   :crying:  

I also couldn't go up in the Sears Tower or the Hancock Tower because the cloud cover was low yesterday and I would not have been able to see much.  It was ok, I did get to see them and that was cool.


I drove by Wrigley Field.  cool.  And I saw, from the road, where the White Sox play.  Again, cool.


I also took pics of a few other buildings.  I walked around downtown and was surprised at how many people were out and about.  I felt pretty safe, but I always feel that way do to what I do.  Anyway, Chicago downtown was extremely impressive!  


The last thing I did was go to my hotel and have a few Stella's and  had a great conversation with a couple of others people who were at the bar.  One was named Makil who was from Miami who was there on business.  He owned a bar with his dad, which I thought was cool, and worked for a tool business. (I forget which one.)  

I also spoke with Michael, don't remember his last name.  This guy was great.  He reminded me of John Candy, heavy, jovial, and funny.  He lived in Washington DC, so of course, politics came up.  Great conversation and very smart man.  I was on him hard during the Washington Redskins VS Dallas Cowboys MNF Game.  Good stuff.  


Anyway, I marked in my mind some of the others sites I'd love to visit the next time I visit Chicago and will look forward too it.


Thanks again for everyone's advise!  You guys/girls are great!



Edited by dallas050
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