Of all the things you listed, the only ones that will take a fair amount of time are the brewery tour, which I understand is a priority, so why not? and the Field Museum -- which is also located a little away from the other "sights" you mentioned. This is totally doable to me, just keep the museum date/time flexible (although I think you can get advance tickets and avoid the lines - don't quote me on that though ).

Second City also has late shows, which might work with your schedule, too.

Not sure you need to see the views from the Sears Tower AND Hancock Building -- one is probably enough.

You might want to add a walk by the lake (no visit to Chicago is complete without that - and you can do that and then cut in to Grant/Millenium Park) and a walk on Michigan Avenue.

If you have time, a Chicago Architectural Foundation architectural river-boat cruise is great --- it's the only way to see the terrific architecture from "the other side".

I could easilty spend an entire day in the Field Museum. Another museum to consider is the Museum of Science and Industry. The architectural river-boat cruise that sf7307 recommended is very interesting. Views from either the Hancock Building or the Willis Tower are fabulous; the Willis Tower has the Skywalk, a plexiglass box that extends out over the street. Very cool if you're not fearful of heights......

FYI, the Cubs dont play many night games so you should plan on them being a Saturday afternoon game (2pm Chicago) start. Most Fridays the Cubs have day games as I listen to them on XM. Having day games, turns into most of the day events at Wrigley due to bar hopping before hand.

That's great to know about the Cubs, because that will def. influence our plans for while we're there..I suppose I can only hope for a night game one of the two days!

Last year when the Cubs and White Sox were both at home over a weekend in August, the Cubs played 2 day games and one night game (Sunday, odd) and the White Sox played two night games and one day game (also Sunday). I think it's planned so they don't play at the same time, so you should be in luck.

I know the brew tour is a priority, but just a thought. If you're pressed for time, you might go to Goose Island brew pub in Wrigleyville. You could grab a bite there before or after the game.

I just got back from my first trip to Chicago. It is a great city. Here's my two cents.

I'd do either the Willis Tower or the Hancock Bldg. and take in the Field Museum or the Museum of Science and Industry. Either museum will take up half a day. Skip the Navy Pier, it has the atmosphere of a seedy carnival. And absolutely take a Chicago Architectural Foundation boat tour. CAF offers bus and walking tours also which would give you a great overall look at the history and culture of Chicago, not just the architecture.

We really enjoy staying at the Chicago Hilton on Michigan Avenue (very near Grant Park) and have looked in the Palmer House - a little further away, but very nice too.

I would strongly recommend that you wait until the next season's schedules are set before making any plans, if the primary objective is going to one or more ballgames. That might be a weekend when both teams are on the road.

More often than not, one of the teams will be on the road when the other is playing at home.

There is the possibility, though, that you might luck into one of the "cross town classic" series, when the Cubs play the Sox. (Some games are played at Wrigley and some at the Cell during different legs of the series.) If this is the case, it is extremely difficult to get tickets for these games. You basically need to purchase them as soon as they go on sale - meaning the very first day as soon as sales start.

Just my two cents here, but if you go to see the Cubs at Wrigley, go during a day game. IMHO, much preferable - and traditional, too.

Quite frankly, you won't have much time to do other things than the ballgames, if you are able to go to both. For one thing, you have to calculate in the travel time. A 1:20 p.m. start means that you'll have to leave the downtown, River North or Mag. Mile areas before noon (and I personally would suggest no later than 11:30ish even using the Red Line) and you wouldn't get back to that area until around or even after 6:00 p.m. because the game will let out right at rush hour (if on a Friday evening).

It would be difficult for you to go to anything with a curtain before 8:00 or 8:30 p.m. (most shows start around 7:00 p.m.), for example.

You might be disappointed with Navy Pier if you are just walking around without having a specific destination there. I'm not sure if that's what Nick above did at Navy Pier. But keep in mind that the Chicago Shakespeare Theatre is one of the best in the city and, if you are planning on a lake cruise, you would be boarding at Navy Pier. Also, if there is a Tall Ships festival next year, that's a very nice event. BTW, the whole reason why there is a *midway* and a *ferris wheel* there at Navy Pier is because these originated in Chicago - at the World's Columbian Exposition of 1893.

Field Museum - allow at least 4 hours. If you are going to take in a special exhibit, they have timed entry - meaning date *AND* hour.

You'll have to include sufficient time for waiting in the two lines to go up to the Skydeck at the Willis Tour. At the busiest of times, this could mean a couple of hours wait time.

No matter whether it's a day game or a night game, you will not be able to attend a 4:00 p.m. Second City performance. If there is a day game, it won't be over yet. If it's a night game, you won't be able to go to the show and make the start of the game.

A visit to the Museum of Science and Industry entails the better part of an entire day due to the travel time there and back from the downtown area and the size of it. I do not recommend this course of action for visitors with such a short stay.

Do you have no interest in going on the Chicago Architecture Foundation's River Cruise or a visit to the Art Institute? The AI is immediately south of Millennium Park and MP is only 3 blocks south of the Chicago River, where the River Cruise takes place.

Just as a final comment, the Northalsted Market Days festival in the Boystown area of the Lakeview neighborhood is usually set for that weekend. This is one of the biggest festivals in Chicago - and midwest, both with respect to crowd-size and area of the festival. It's only a couple of blocks from Wrigley Field to the east on N. Halsted. So there is usually a lot of traffic going to and from the festival area via bus but on the 'L' too. Another reason why you would want to allow sufficient travel time, even taking the Red Line.

You might also be interested in taking a tour of historic Wrigley Field. You'll find information on the Cubs website about them.

Exiled, the baseball schedules have been released and both teams are home that weekend. The only TBD are the gametimes.OTher than that, I completely agree with your post and hope the OP takes this into consideration.

Thanks, folks. I apologize for not checking on the schedules first but please put that down to time restraints. So much to do, so little time, eh?

Anyway, just a couple of wild guesses here, but it might be that most of the Cubs vs. Cincinnati series will be day games, whereas the Sox vs. the A's will more likely be at night, due to time zone differences. Of course, there's no telling because of the televised situation.

If that is indeed what happens, IMHO, you'd be best to go to the Sox on Friday night and the Cubs on Saturday, if you can fit that into your schedule. You won't be able to attend any games in their entirety on Sunday, and I don't think you want to just go for 4 innings or less.

You'd also have to sacrifice the Saturday brewery tour. And, if you go to 2 games, I would also recommend foregoing any museums, unless you are planning on doing that and only that on Sunday morning.

Unless you are willing to forego one of the games, scratch Second City from your list - UNLESS you go to a Cubs day game and the latest show possible (probably not possible to make the 7:00 p.m. one, though).

What I would suggest, though, is this: Take a look at the Explore Chicago website to get an idea of all the possibilities which you have. Pay particular attention to the free Chicago Greeter service, especially after reviewing the neighborhood section.

If you have a night game on Friday night, for example, you would have about 4 hours at your disposal, once you get all settled into your hotel. You could use that for perhaps taking a CAF River Cruise (figure 3 hours total when you include standing in line for boarding and disembarking) plus a nice walk down to Millennium Park for an hour.

If you have a Saturday day game, you basically have the morning to explore areas of the city. That's where the Chicago Greeter service comes into play. I would suggest that you look at the areas which are immediate to the Red Line - and they would be, basically, the downtown (Loop), River North and Mag. Mile areas; the Gold Coast and/or Old Town; Lincoln Park; and Lakeview.

Sunday, you'll basically have 5-6 hours at your disposal but it will have to be someplace close to your hotel because any travel time will eat into those precious few hours.

If everything works out for you, perhaps you'll be able to get sufficient time to see the more "touristy" areas the first day - this being your first time - then venture out a little the morning of your second.

Thinking of it, here are some other suggestions: If you go to a Cubs games, you could go to Hopleaf in the Andersonville area of the Uptown neighborhood of Chicago (depending on what transpires). Andersonville is about 15-20 minutes north of Wrigley Field via the #22 Clark St. bus. hopleaf.com

However, please keep in mind that traffic is just a zoo after a Cubs game, especially one on a weekend. You might just wish to walk over to N. Halsted on Addison (about 4 blocks east) to see what's going on with Northalsted Market Days. They have 3 or 4 stages of live music going throughout the day.

Besides the Pride Parade and festival, held the last weekend in June, this is one of the biggest festivals of the GLBT community in the Boystown area of the Lakeview neighborhood. (Wrigley Field is in the Wrigleyville area of the Lakeview neighborhood - immediately to the west of Boystown). The crowd is mixed, as this is one a very popular festival in Chicago: gay, lesbian, straight, bi, etc.

Although it's too early at this stage, here is the website where you'd be able to find information on that festival: www.northalsted.com and here's the website for the East Lakeview area: www.lakevieweast.com

Another area which is fairly close to Wrigley Field is the N. Southport corridor area - a little more than 5 blocks to the west. It's a nice walk after a day Cubs game and you'll probably even be walking faster than the vehicular traffic on Addison. The N. Southport Corridor is anchored around the historic Music Box Theatre and contains boutique stores and restaurants, as well as a live theatre venue. Further south on N. Southport are the N. Southport Lanes and Billiards (where the pins are still set by hand and Schuba's (a live music venue), both of which used to be Schlitz brewery houses. You can easily tell this from the facades of the buildings, which feature the Schlitz logo.

You could also go up to the Green Mill (jazz club), if you wanted to make a full day of it on the north side. Take a look at the history on their website: www.greenmilljazz.com All you have to do is take a ride on the Red Line up to the Lawrence station, although I do recommend that you cab it back at night.

There's also tours at the Goose Island brew pub at the N. Clyborn location -
Tours and Tastings:

Saturdays at 12:30pm, 2pm and 3:30pm
Sundays at 1:30pm, 3pm, and 4:30pm
Duration: 60-90 minutes
Reservations are required. Please R.S.V.P. by calling us at (312) 915.0071. Must be 21 years of age with a valid ID. Cost is $10 per person.

Chicago is amazing. I'm sure people will chime in with a multitude of fine dining spots, so here's a few of my favorite casual places: Goose Island Brew Pub (good food, beer, cider),Fado (Irish Pub. The Chicken Boxty Quesadilla is great), Gino's East (on Wells for my favorite thin crust pizza), PJ Clarke's (for the best macaroni & cheese), Heaven on 7 (truly heavenly cajun food and gumbo), China town for dim sum, Hugo's Frog Bar (on Rush)

I don't recommend taking a taxi from the airports. The L from either O'Hare or Midway get you into town without sitting in traffic or the expense.

Some of my favorite things: Museum of Science and Industry, Field Museum, Shedd Aquarium, Adler Planetarium, Oriental Museum (near the UC main campus, free, amazing artifacts from the early civilizations in the Mideast), the free audio tour of the Chicgo Tourist Center at Michigan and Washington?/ Randolph?, Chicago Historical Society, Millenium Park, Navy Pier, Museum of Contemporary Art, walking the lake from the Ohio St, in fact walking anywhere ogling the architecture, the small local theatre offerings, scoring 2 fers to the "Broadway" shows. Sorry, I could go on forever.

We lived downtown near Navy Pier for 3 years before moving to SW Florida to escape the cold and found we missed the city every day since. Miss it so much we're going back in December to look for an apartment in Streeterville to escape to whenever the mood strikes. May sound odd, but there's only so much sun, beach and tennis one can take.

exiledprincess -- you made some great points. Ditto for Hopleaf in Andersonville, but I am not sure if they are open for Cubs day games.

Plus, if that weekend is Market Days the neighborhood will be NUTS! I live in East Lakeview/Boystown and the traffic is a nightmare during Market Days (especially if the weather is good).

If you make it to the Cubs game, check out Sheffield's. It's on Sheffield and School and has an awesome beer list and beer garden. Plus they have great food.

Skip Navy Pier. I highly recommend the CAF cruise. The architecture is so amazing.

I am originally from NYC but also lived in Chicago twice and love it..The Field Museum is wonderful ; it's similar to the Museum of Natural History in NYC..The Museum of Science and Industry, however, is different and a real gem. I love the Art Institute of Chicago. For a unique Chicago activity I highly recommend that you take the Chicago Architectural Foundation's river cruise where you'll learn and see a lot about Chicago and it's history.You can buy tickets online.
Sounds like a great week-end..