Visited Chicago over the weekend

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For our one-year anniversary, my wife and I visited Chicago for a 3 day, 2 night weekend trip. We stayed at the Trump Hotel (which is outstanding in every single way), and did as much in the city in 3 days as we could, even though it rained parts of all 3 days.

I'll start off by saying that neither of us had ever been to Chicago before. It's only 5 hours or less from where we live, but we had still never been. The first day we got there we visited the Shedd Aquarium with full-access tickets so that we could see everything. We spent a good 5 hours there, and both of us were absolutely amazed by how beautiful that place was. Later that day we ate at Rosebud's on Rush St. and loved the food. We will be going back there for sure!

We did lots of shopping the second day there, and also went to the top of the John Hancock building and did the audio tour. Afterwards we ate at The Cheesecake Factory. A couple of years ago, we almost got one built a couple miles from where we live, but the city turned The Cheesecake Factory down
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It rained a good portion of today, but we still did some shopping and spent some time in our hotel. The rain prevented us from visiting Millennium Park, though.

Overall, our trip was wonderful. And I have to say that I was extremely impressed with the cleanliness, liveliness, and things to do there were in Chicago, and we only barely scratched the surface. Don't get me wrong, I love Detroit and its downtown area. But outside of Greektown, there's not much to do, in my experience. Chicago was clean, friendly, and presented us with so many things to do that we didn't know where to start. Oh, and the public transportation was wonderful! A+ weekend for sure, and we can't wait to return to Chicago!
 
I'm not a big fan of cities but I have to give it up to Chicago (South Side excluded). It truly is a big city but in a weird way has a small city feel to it and is very clean like you mentioned. Wrigleyville is a blast beyond description. Glad you enjoyed the visit! Only thing I don't like about Chicago is the tax rate, I bought a $50 sweatshirt and it ended up costing me $58 after tax if I remember correctly.
 
I'm glad you mentioned the tax rate, because it is insane! I calculated it based on one receipt that I had, and it was like 10.7%! Does Chicago have a different tax rate than the rest of Illinois? All of Michigan is at 6%, which is relatively low and quite nice. Isn't Ontario at 15% or so?

Besides the tax rate, the only gripe I have about Chicago is that you get raped on parking everywhere. Thankfully, we were able to keep our vehicle parked at our hotel for the duration of our stay (still $118 in total, though), but every garage I saw was outrageously priced. I guess that's fitting though, since Chicago is such an attractive place to be.

I felt kind of out-of-place parking in the Trump Hotel garage. On the way to finding a parking spot, just in the garage alone, I saw an AMG SLS, a Bentley Continental Coupe, and an F430 spyder, and at least one Porsche. My little Focus was surely out of place
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When I was in Illinois in the 80's I went to Chicago numerous times and enjoyed the city (except South Side) each and every time. I had been in So Cal for more than 25 years, LA is less than 45 minutes drive but I rarely go there, probably no more than 4-5 times.
 
Yes the rest of Illinois is different. Down where I am, way in southern Illinois we have an 8.25% tax rate.
 
City parking in San Francisco is similar and probably the same as any US city. Garages attached to hotels are $40 - $50 a day, but nearby there are others available for as low as $10 a day. But you have to be careful about the exact area.

Yelp helped me to find a $10 garage that was highly recommended and well located. When I got there, the reviews were right, it was clean and brightly lit, and I parked next to a Maserati so I knew it was safe.

I did a similar thing to you, 3 days, 2 nights, and my final parking bill was actually just $10 as I managed to park for just under 48 hours and they only charge $10 per full 24 hour period.
 
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I love Chicago. Among my favs in the states along with San Fran and NYC. I visit several times a year. But the best city I've visited is Sydney Australia. I was just there a month ago and all I can say is Wow. I wanna retire in Australia.

As for parking in Chicago, there is a garage on Kinzie between Clark and LaSalle north of the river. The entrance is right before the CVS pharmacy. On weekends it's $8 per 24 hours. You can't find a better location and it's cheap.
 
Chicago is a great city. I used to go to grad school at Purdue University about 120 miles south, in Indiana. Occasionally on weekends, I'd drive to Chicago to escape the miserable life of grad student. I like the Chicago city center, the loop area, with its magnificent mile, sky scrapers, and museums, etc. However, I don't really like being caught up in the so called "tourist traps" too much. One of my favorite things to do was to park my car somewhere away from city center and then walk around, usually towards the loop area.

Typically, I'd park my car for free along the Irving street and then walk south towards the center along the shore, dropping by the free Zoo, getting a $5 haircut along the way, having a few beers at a local bar with a bunch of Polish-Americans,etc. By the time I get to the city center it gets dark. Then I took the train to the area where I parked.

Another thing I tried is leave a car in down town parking, then rent a bicycle and ride around. One day I took a ride to the south side along the shore, then went west to see the Hyde Park area, where University of Chicago is, rode along the block where President Obama's house is, and then rode back. The south side area does look relatively run down, except for Hyde Park area.

Fun time. I hope to visit again.
 
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Originally Posted By: Klutch9
I'm glad you mentioned the tax rate, because it is insane! I calculated it based on one receipt that I had, and it was like 10.7%! Does Chicago have a different tax rate than the rest of Illinois? All of Michigan is at 6%, which is relatively low and quite nice. Isn't Ontario at 15% or so?

Besides the tax rate, the only gripe I have about Chicago is that you get raped on parking everywhere. Thankfully, we were able to keep our vehicle parked at our hotel for the duration of our stay (still $118 in total, though), but every garage I saw was outrageously priced. I guess that's fitting though, since Chicago is such an attractive place to be.

I felt kind of out-of-place parking in the Trump Hotel garage. On the way to finding a parking spot, just in the garage alone, I saw an AMG SLS, a Bentley Continental Coupe, and an F430 spyder, and at least one Porsche. My little Focus was surely out of place
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Downstate a couple of towns are @ 9%!
 
In the 90's I lived in the area you were hanging out; a block from the Hancock Bldg & the Cheesecake Factory. It was fun back then and I'm sure even better (and more expensive) now. Glad to hear the Near Northside is still a great place to visit.
 
Taxes....
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Illinois has a state sales tax, counties impose their own taxes, cities impose their tax, if you're in the 6-county region in/around Chicago, there's an RTA tax to fund transit, and so on. Some of the suburbs are as bad as Chicago as far as a 10% total sales tax goes. And Chicago even imposes a 5-cents/bottle tax for bottled water. Rumor has it that there's even a tax-tax....
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I haven't been to the Sears Tower since they put the sky boxes in (you can call it the Willis Tower, but it's still the Sears Tower), but I was at the Hancock when they added the "porch" and thought it was pretty cool. Glad to hear you enjoyed yourself. I'm one of those evil suburbanites who just goes downtown to work, so I'm a bit jaded when it comes to the touristy stuff, kind of someone who's lived in NYC all their life and never went to the Empire State Building.
 
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