Wow, thanks so much, everyone!

@exiledprincess - You've practically planned the whole trip for me...thanks! I'll have to map it all out for myself so Ican have it handy and not waste time.

But what do you mean the Venetian Night is a thing of the past? The link I enclosed (earlier) is current. Otherwise, great input!

@blueslipper - I'd do a bike tour, except for crazy hot weather - which looks like I'm almost guaranteed.

@ChiSue - Thanks for the tips! But don't display my phone on the El and on the streets? My face is often in my phone and I rely on it for everything, esp getting around. Doesn't everyone? Now I'm worried...

I'm very appreciative of all the information from everyone! I will be posting more questions as my departure date becomes more imminent, and definitely while in the city.

Now all that food talk has made me feel very, very hungry!

I'm eavesdropping on all the great info on this post for my trip early August

My favorites, in terms of museums, are the Art Institute and the Chicago History Museum. If you go to the Chicago History Museum, definitely walk through the zoo....but it's not like the San Diego Zoo (imho). Also, you might want to check out groupon, living social and the other similar sites. Groupon (I think) recently had a great deal on the CTA pass for three days.

It was Groupon - they had bought up thousands of the passes and were selling them at a discount from face value.

sf7307, the OP is coming next week so there isn't sufficient time for them to order them through the Groupon offer. I mentioned this in my first response on this thread.

@OP: Venetian Night (in the past) consisted of two portions - a decorated boat parade and an impressive City of Chicago fireworks display. There hasn't been a Venetian Night in Chicago for several years, as it was canceled in 2009 due to budgetary restraints.

After you questioned me on this, I did a little research into it. The Chicago Yachting Association does have an application up on their website for an August 4, 2012 Venetian Night event starting at the 31st Street Harbor (in association with the Mayor's Office of Special Events).

However, since the City of Chicago didn't have a 4th of July fireworks display this year (Navy Pier did), I would assume that the City would not be providing the fireworks display for a Venetian Night, if it does come about. Perhaps the boat parade will just be in addition to the regular Saturday night fireworks display from Navy Pier.

The Explore Chicago I mentioned above is the official City of Chicago Tourism Department website. I did a quick search there and don't find any mention of a Venetian Night, even using August 4 as the date in an advanced search. Perhaps the idea is just in the "maybe" stage at this point, depending on if there is sufficient interest in reviving the boat parade.

Sorry, a correction: I meant to say there hasn't been one since 2009.

@tomfuller - Thank you, adding that to my list.

@MP07950 - I did see that CTA deal on Groupon but at that point, wasn't decided on my destination yet. Plus, I think it was for 3 days and I will be there for 6. However, I do have the Groupon app on my phone and will check it frequently for local deals. And I agree that the San Diego Zoo is awesome. Thanks!

@exiledprincess - I also researched the Venetian Night event and found it hadn't occurred since 2009. Apparently, there are chartered yachts that try to somewhat replicate the experience, but nah..I wasn't looking for that.

Also, I'm assuming after a day out and about in the hot sun, I'll want to rest up in my hotel. However, I do tend to go for the overkill when in a new city and try to do as much as possible, but what's one to do at night? Solo, that is? I'm imagining like any other big city, it's the theater/bar/club/dinner thing..which I won't want to do alone. But is there anything else unique that I'd want to see at night, aside from the Willis Tower observation deck at dusk?

So far, it looks like my first full day will be to head to the Chicago Arts Institue, as they're open later. I have read it can take an entire day to see, but neither The Smithsonian National Gallery of Art nor The Louvre have taken me a whole day...but about 5 hours, yes.

I'm still mapping out the rest...based on weather, etc...

Just a friendly reminder - those that contribute here don't make itineraries. We only mention items for people to consider. The proper research is your own task, to make your visit what you want it to be.

No, it wasn't the City that provided the boat parade in the past. These were privately-owned boats and yachts which were decorated in the parade. The Chicago Yacht Association was involved then, too.

What I was trying to relay is that, should this come about again this year, it most certainly won't be the same as in the past. Just like the Taste of Chicago and Independence Day.

People need to understand that, especially under these continuing economic times, events and attractions which don't pay for themselves in some manner will be substantially reduced in stature or won't exist any more. For example, I read threads about people wanting to take their own food and drink to a free music or entertainment festival - when the sponsors are there for exactly that reason. If you don't get sufficient sponsors, you won't have that festival anymore.

Not to get on a soapbox here, but the futures of these institutions, events and attractions all ride on our shoulders. So, I'm kindly suggesting to everyone, if you do find one that is free (i.e., the Lincoln Park Zoo), please contribute a donation of whatever you can reasonably afford, even if it's only a few dollars. Otherwise, maybe in the (very) near future, we'll be talking about other events/attractions here which were free or low cost but are no more - or cost you the $$.

You'll find out that the Art Institute of Chicago isn't just about paintings and sculpture but also includes architecture (including the building itself, especially the Modern Wing), textiles, medieval armour and arms...

Evening events: Chicago is one of the most vibrant theatre destinations in the world. I'm sure you'll find plenty to do after hours if you just do a little research on that Explore Chicago website.

@exiledprincess - Yes, thanks..but as I said in my earlier post, I didn't want to do the theater/bar/club/fine dining available in major cities on my own at night. I was looking for alternative options, if any.

If you find yourself near the Hancock building and need a light meal or snack, there is a bakery in the plaza area at the bottom of the building on the end opposite The Cheesecake Factory. They have baked goodies as well as sandwiches and salad. The gelato is wonderful.

@gardendiva Thanks for that tip!

Well, I'm seriously bummed!

I have to reschedule my trip to the Fall. A major project came through at work that requires me to be present this week.

Just wanted to thank everyone for all your tips. I will save the info for my trip later this year - potentially October, if it's not too cold!

If you do Hancock building, do not do the observatory. The charge for the elevator ride is pretty steep. For much less money you can do 96th Lounge, only 1 floor below and the elevator ride is free. So you can have a beer or a drink and have the same views for about the same cost or possibly less than the Observatory.
http://www.signatureroom.com/Signature-Lounge/

You should consider doing a Chicago tradition for lunch, an Italian Beef sandwich. It's truly a pure Chicago deal. Al's #1 on Taylor Street is one of the better ones. The Italian Ices place across the street is just the right place to finish up your lunch.
http://www.alscatering.com/

I would also consider some ethnic neighborhoods for inexpensive food and interesting observations. German, Mexican, Chinese, Polish neighborhoods come to mind.

oh, one more suggestion,

for a really magnificent zoo experience, although it qwill set you back few $, look into Brookfield Zoo.
http://www.czs.org/CZS/Brookfield/Zoo-Home.aspx

Thanks, @AAFrequentFlyer!

Since you delayed your trip, try to find lodging at the HI Hostel. From O'Hare take the Blue Line to Jackson and then walk south for 4 minutes to get to 24 Congress Parkway. The red line turns the corner right next to the hostel. That would be the one to go back to the airport I believe. The upper floors of the hostel are used by college students as dorms.