Our first visit to Chicago will be the 2nd weekend in May. We're going with another family and our 4 boys are ages 21, 22, 23. Adults are mid-40s. What are the first-time touristy things we need to do? I have listed Navy Pier, Sears Tower, Field Museum, Shedd Aquarium, Museum of Science and Millennium Park, along with Mag Mile stores. We'll be there several days. What's a good hotel that isn't luxury? Is Sheraton by the River good? The boys will probably ditch us come late evening, but this is a "family" vacation so they'll probably hang with us for the most part. Any help appreciated. Thanks.

I think you should ditch Sears Tower and go to the top of the John Hancock Building for drinks... much better view of the skyline (and it's free, just the cost of the drinks).

Get Chicago passes for multiple entries.

www.metromix.com will have some details and lots of info for your time frame.

There are tons of threads on this subject right here on Fodors. You can search on Chicago Field for example and get lots of details that will help from past inquiries.

The River location is the best in my book. It's central to both N. Michigan and Museums/shows in the downtown area which is called the LOOP.

I would add Art Institute absolutely. It is beyond world class, if there is such a thing. Navy Pier in May is ok but it is just some cheaper shops, so-so restaurants, a ferris wheel, and an IMX for the most part- unless you are going to an enterntainment venue there, it just won't take much time.

Also for that week absolutely inclue the Chicago Architectural Foundation's river cruise that will take you up the Chicago River.

The hotel question is so hard to answer because there are literally a 100 hotels that would probably not be considered 4 or 5 stars. I have stayed at Hotel Allegro, Hotel Burnham, Intercontinental in the last 2 years and they have all been good.

I'm not sure where the Sheraton is on the River, but it must be right off Wacker or across the bridge. That's a good location.

Go to a Second City mainstage show! And check hottix.org for other show tickets. Day-of-show tickets are discounted about 50 percent. Best availability is Tuesday-Thursday.

Visit a blues club - Buddy Guy's or Blues Chicago have consistently strong acts.

Eat, eat, eat! We didn't get to be "America's Fattest City" by skimping on the cheese fries!

The Sheraton is a nice hotel with a good location. I've never stayed there but been to several events and conferences there. I agree with skipping the Sears Tower unless you have a serious desire to see it. If you are wine drinkers, there is a great wine bar on West Randolph that has a fabulous view of the skyline on a clear night-It's called the Tasting Room. If you are baseball buffs, you may want to treck up to Wrigley Field and check ahead of time b/c they offer a good tour on non-game days that are pretty cheap. The info is on the Cubs website.

Also, if you like live theatre, I would search and get tickets for at least 1 good show ahead of time.

Wicked is very good and would be available until April, I think. But it may have been extended again. Check Cadillac Palace Theatre and Ford Theatre for the Performing Arts to see what some of the picks may be for your time frame.

another idea is to just call some of the really classic hotels...Drake, Intercontinental, Omni Ambassador East and just ask about special weekend rates. Given the ages of your boys, they might like Second City, Blue Man Group, check out who's at the House of Blues, segway tour, rollerblading along the lakefront, Cubs/Sox may be in town as well.

Some good links here:
http://www.chicagotraveler.com/index.html

and here are the segway tours (great suggestion, guys will love this!)
www.citysegwaytours.com

JJ5, You'll be happy to hear Wicked has just been extended to July 30. I just purchased my tickets for June 24!

You will be in Chicago at a great time of the year. You might try the Embassy Suites as they usually include a hot buffet breakfast and an indoor pool as well as some hotel space. I think there is one near Mag Mile off Ohio or Ontario. If you go to see Wicked, we had an awesome plated brunch at the Atwood Cafe one block from theatre and great deal for parking ($15 for whole afternoon!). It's probably too early for Oak St. Beach, but don't miss the zoo, it's one of our favorites and you can get there via city bus. There are lots of little neighborhoods to explore, depending on what kind of food/shopping you like. The Adler planeterium isn't on your list, and it has one of the best views of downtown Chicago outside it. Big second on the Arch cruise, just watch out for tour buses emptying their john (just kidding Dave Mathews Band). Have fun!

Leta, definitely:
1. Do the Chicago Architecture Foundation's River Cruise.
2. John Hancock Building (Signature Lounge). Go just before sunset.
3. Take a boat ride on the lake and see the city skyline from it (preferrably at both day and night, but if you had to pick only one - night) - even if it's only the harbor taxi from the Museum Campus (where the Field Museum, Shedd Aquarium, Adler Planetarium are located) to Navy Pier or vice versa.
4. Millennium Park and the Art Institute - and Buckingham Fountain at night.
5. Go to a jazz or blues club (maybe both?). The Green Mill (jazz) was frequented by Al Capone. Great place, one of the true must-sees in the city. Andy's Jazz Club has jazz at lunch (no cover then). Buddy Guy's Legends.
6. Walk, jog or bike along the lakefront trail - goes for miles along Lake Michigan (definitely, definitely do travel south from North Avenue to the top of the Magnificient Mile). Walk, jog or bike in Lincoln Park. There are also segway tours but check out Bobby's Bike Hike.
7. Go to a Cubs or Sox game.
8. Take a ride on the El.
9. Go to a comedy club (Second City, Zanies, I/O (fka Improv Olympic).
10. Go into the neighborhoods--Chinatown, Greektown (for dinner), Lincoln Square, Lincoln Park including Wrigleyville (your boys will like those last two, especially), etc.

Have fun while you are here!

In above message, "must-sees" should be "must-dos". Sorry.

just back from a rtw trip which included a 4 day 'stop over' in chicago. we thoroughly enjoyed eating at Grand Lux Cafe. Its huge , but we thought a great atmosphere for a casual very busy cafe. And the menu alone takes a good 20mins to read properly. Treat your self to the Strawberry Shortcake..........an absolute delight.

we didn't get Navy Peir. Nice from the outside but we found it a bit 'tacky' and had a 'carnival' feel to it, that we just didn't get.

But we loved chicago. We stayed at a Holiday Inn, but found it a bit far from Mich Ave etc.

The Sheraton Hotel by the river is fantastic, plus a great location.Navy Pier is a waste in my opinion...not real Chicago. Make sure you ry some Chicago deep dish pizza. There are many options. Chicago is a great, clean city.

Sheraton by the River is great, where former Pres Clinton stays. Anyplace downtown will be fine adn transit is easy. Lots of good suggestions, I'll add my 2 cents

1. Wicked may be ok for you but your "boys" have many more choices I am sure they'd prefer. Do a group trip to the Second City Improv for all of you.
2. You can rent bikes at Navy Pier and cycle the lake front
3. Skip Sears Tower and the observation deck fee and head to the lounge at the 96th fl of the John Hancock bldg, have a drink while looking over the city, amazing.
4. Take the Red line from downtwn to a baseball game. Sox or Cubs may be in town. If not, still redline up to Wrigley and walk aroudn teh neighborhood. The "boys' will love it.
THey'll also love Armitage Ave in Lincoln park if they are single watch all the young ladies shopping and boutiquing.
5. ARchitectural cruise is a do not miss for all
6. Navy pier, head to the far E end to the beer garden for free music!
Millenium Park is amazing, there's a fun putting green at Monroe and Columbus, pretty difficult actually.
7. Lincoln Park Zoo. Free, in the city, just amazing. Get there early to avoid all the strollers if it's a really nice day

metromix.com let's you search by dates for festivals and events
also see choosechicago.com

My 19 - 23 year old kids love Second City. If you go, book your tickets ahead of time because they always sell out. And get there early so you can get good seats along the railing of the balcony. Otherwise you might be kind of crammed in. Lots of restaurants nearby.

Thank you very much to everyone for all the great suggestions.

Tagging this discussion for our visit to Chicago in late April for a relative's wedding. All the good suggestions may work for us.

Not sure where you are coming from, but be sure to pack a jacket or long-sleeved clothing. We took the Architectural River Cruise last July and nearly froze during the evening (temps in the 50s).

Have a great time!