What to do in Chicago?

elphaba91

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Jul 12, 2013
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So I have booked a trip to Chicago for 4/5 days in January, without really knowing too much about the place! (We originally planned for that leg of the trip to be San Francisco, but the accommodation was weirdly expensive so as I could get Hamilton tickets we changed to Chicago!). I'm super excited to go somewhere new though!

So, any Chicago locals or those who've travelled there, any advice for what to see/do?

My typical travel style is to walk from landmark to landmark, soaking in the architecture and feel of the place; I am usually quite happy just seeing things rather than having to actively do things. However, I know it will be freezing so I think some indoor activities are a must!
 
Not sure if you have kids, but The Museum of Science and Industry is my absolute favorite. So many fun and interactive things to do. They might still have their trees up too, they decorate hundreds of Christmas trees and each one is in the style of a different country.

You can go ice skating at Maggie Daley Park. Haven't been, but heard the park is pretty cool and they open an ice ribbon to skate on. It is right by Millennium Park too so you can see The Bean.
 
So I have booked a trip to Chicago for 4/5 days in January, without really knowing too much about the place! (We originally planned for that leg of the trip to be San Francisco, but the accommodation was weirdly expensive so as I could get Hamilton tickets we changed to Chicago!). I'm super excited to go somewhere new though!

So, any Chicago locals or those who've travelled there, any advice for what to see/do?

My typical travel style is to walk from landmark to landmark, soaking in the architecture and feel of the place; I am usually quite happy just seeing things rather than having to actively do things. However, I know it will be freezing so I think some indoor activities are a must!

Well, then you're going to love you some Chicago. The architecture alone is worth going for. Bundle up well, and then pop into the many (!!!) Starbucks to warm up occasionally.

As far as food, you *have* to go to Portillo's for a hot dog, Garrett's for popcorn, and at least a couple of pizza places.

Where are you staying?
 
Museum Campus-Shedd Aquarium,Adler Planetarium,Field Museum.More restaurants than you can shake a stick at.Lincoln Park Zoo.Shopping galore.The Riverwalk.The Art Institute.Millenium Park.You'll have a blast!
 

Second city! It is always hilarious!

And pizza at Giordanos.
 
We did an architectural boat tour last time we went. It was amazing!
 
Thanks for the replies so far!

I should clarify that it is just me (26) and my sister (23). She is finishing up her year in Orlando doing the Disney International Cultural Exchange Program and I'm going to 'pick her up', then we'll head to New York, then Chicago before 1 night in LA and then home.
 
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I’m not a local but visited Chicago for the first time this summer and loved it!
We went to Museum of Science and industry and spent the whole 7 hours they were open there. Also did Skydeck, Field Museum, the aquarium and Art Institute.
Spent half day at Lincoln Park Zoo.
It was summer so we went to a Cubs game. Also rented bikes and biked around the lake.
Tried 2 rival pizza places.
It was fun!
 
Chicago is an amazing city. The Symphony is World Class, the architecture is so beautiful. The Art Institute is just incredible. Have a great trip.
 
Oohhh winter in Chicago. Yikes

Do inside stuff. It's COLD downtown! Most of the museums are decent. I'd personally go to the Field Museum or MSI, and skip the Shedd, but that's just because I'm not huge fan of spending $40 to look at a bunch of fish. I'd skip Grant and Millennium park because it will be NO FUN when it's freezing. I'd go to Michigan Ave by the water tower and walk around - you can duck in and out of shops to stay warm, and there are lots of places to choose from to eat. Go to google maps and look for restaurants in the area you want to be in so you don't get stuck with the same old Giordano's, Cheesecake Factory, and Portillo's that everyone goes to. (unless of course, that is what you are looking for! And, by the way, just a little tidbit - I pass the Portillo's owners daughter's mansion in the western suburbs on my way to work every day ::yes::

Most of all, I would plan to come back in the summer. It's so much more fun!

And FYI - the Sears Tower is $23.00 just to go up there....and doing the express line is almost $50. I guess it's worth it to do it once? :confused3

Just be aware that the Sears Tower isn't really by anything else except Union Station and now there's a little riverwalk-ish area there, too. The MSI is a few miles south of downtown and isn't walkable from downtown or accessible by the El - you would have to take a bus, cab or uber if you are not driving into town. The rest of the touristy stuff is mostly on the Northeast side of town. Learn the bus and El system and you should be fine!
 
I'll second Museum of Science and Industry. It is an amazing place and lots of fun! I haven't been in years, but it was always pretty great. The Shedd Aquarium is also very nice. Make sure to get some real Chicago style pizza!
 

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