I'm taking my boyfriend on a surprise weekend to Chicago just for fun! We're staying at a Wicker Park B & B. Where should we eat/shop/hangout?

For quirky, fun, and (actually) pretty good food; have a "Cheezboiger, Cheezboiger" at the Billy Goat Tavern. It's located at 430 North Michigan in the center of downtown.

Navy Pier has a very festive and fun atmosphere. Riva has good food and and nice view. Bubba Gump's Shrimp waitors may quiz you on the movie details. Lots to do there and it can be fun with the sculptures etc. and might be romantic. Can take a boat ride etc. etc. etc. Some time in the Art Institute might be fun if he likes art and people watching too.
Have a great weekend! J

Michele, Don't miss the Blueman Group. Check it out on www.blueman.com. It is absolutely the definition of "quirky and fun" not to mention "over the top"!
Maria

If you are wine drinkers, the best wine bar I've ever been to in my life is Webster's Wine Bar, 1480 W. Webster Ave. in Chicago. They have live music some nights. The best thing about the place is that they make it easy to taste several different wines by serving tastings in "flights" -- e.g. a flight of 3 Argentinian reds, or a flight of 3 New Zealand whites. I love it there, and some of the food isn't bad either. You can read more about it at:
http://chicago.sidewalk.citysearch.c...IL/0000/12/63/

For food, a really fun place with delicious food is Cafe Ba Ba Reeba (I think that's how it's spelled), which serves Spanish food, mainly assorted tapas. I hope it's still there.

Also, I love Carson's Rib House, the Original Pizzeria Uno and Due, and Giordano's (especially their spinach pizza).

For shopping, Michigan Ave. is the place!!

Go to "Greektown" and have dinner at The Parthenon (314 Halsted). It's pretty, noisy, wonderful food, and great fun...get the flaming cheese appetiser! Stop off at the bakery down the street for fabulous goodies.

oops -- that's South Halsted!

Thanks everyone! I'm writing all of this down and appreciate the info! I hear that the Blueman Group is something to see. KEEP THE RECOMMENDATIONS COMING! Oh, should we see a Cubs game??? He'd love that? Are they hard to get?

Forgot to mention -- if you like comedy then don't miss a show at Second City.

Also there used to be a great champagne bar called "Pops" which had an enormous selection of champagnes and good music -- don't know if it's still there.

There are also some fun bars in Wrigleyville near Wrigley Field but I'm blanking on names.

Hesitated to reply earlier, since my first "quirky" recommendation was covered in the mention of the Billygoat Tavern. Only thing left out was that it is subterranean, under the bridge at Michigan Ave. and the river.

Blue Man Group is a touring show that originated (I think) in NYC at least 5 or 6 years ago, but I hear it's gun.

Since someone mentioned Second City (Belushi/Ackroyd breeding ground) and ribs separately, I'd suggest a stop at the Fireside, a rib joint next door to Second City.

Way up in a neighborhood I couldn't name somewhere near Lincoln Park and Lakeshore is a quirky spot called Club Lucky. Good food, great martinis.

For those who mentioned Halstead in all its geographical forms, I would suggest that Kingston Mines is still the closest to real Chicago blues this repeat tourist-on-a-mission has found, in spite of its lamentable recent renovation to make it more "roomy" and less sweaty and smoky.

Also on Halstead, the best little Italian spot I have found in many a city for good basics and spectacular Tiramisu is Trattoria Gianni near the Steppenwolf Theatre. (Hey, rather than catch a road show of Blue Man Group, you might check out the REAL theatre offerings at the Steppenwolfe.)

I am also a fan of the Field Museum and the Art Institute, but for its small size the Terra Museum of American Art on upper Michigan near the water tower is a treasure.

1) Boat tour offered by the Architecture Foundation. It's a greta way to see the city from a different perspective and a fun/interesting way to learn about why/how Cicago became so significant in architecture
2) A quicky but fun - see the Bicycle Museum on Navy Pier.
3) Art Institue of Chicago - one of the truly great museums in the world and one can go in for a few hours without feeling overwhelmed by the scale and as though there's just too much (although I copuld spend days there)
4) Skip the observation deck on the Sears Tower and the Hancock Building. Go to the restaurant in the Hancock around the 85th floor and have lunch. Floor to ceiling windows on three sides with an amazing view for the city and the lake. The food is surprisingly good and the atmosphere subdued and genteel.
4) If (only if) you're REALLY into blues music, skip the yuppie blues bars and get a cab down to the New Checkerboard Lounge on Muddy Waters Blvd. It's an authentic blues club with amazing music - clientele is mixed between blues aficionadoes who travel from afar and neighborhood residents. I wouldn't walk there and back but it's a very friendly establishment and has been around for many years.

You didn't say how quirky you wanted, The Baton club at 436 N. Clark is quite quirky, they do several shows a night with female impersonators. I haven't been for years but I thought it was a hoot! They fill up on weekends so call for a reservation.

There's a couple of good places for Spanish tapas and sangria, Cafe Ba Ba Reeba at 2024 N. Halsted which was mentioned earlier and also Cafe Iberico at 739 N. LaSalle. Both of these places are packed on the weekend so you might try to call and get reservations.

There's a fun bar if you're into 70's and 80's music called Polly Esther's at 213 W. Institute.

You can find more information on all of these at www. metromix.com and you can see the menu for Cafe Ba Ba Reeba, along with all of the other Lettuce Entertain You restaurants, at www. leye.com.

Someone else mentioned dining at the Hancock Building, it's actually the Signature Room at the 95th Floor, but you can also just get a drink on the 96th floor for about the same cost as the admission to the observatory.

You might also want to check if there's are any festivals that weekend at www.chicago.il.org under the event calendar. There are a lot of festivals during the summer months, the bigger ones in Grant Park and smaller ones in the neighborhoods.

It's me again! What about Taste of Chicago? Worth going or too touristy?
M

Michele,

We loved taste of Chicago when we went one summer. We actually booked our vacation around this event so that we could spend a day there. I don't know how the locals feel about it, but for us tourists it was great!!! It gave us a chance to sample lots and lots of great food and watch lots and lots of people!!!! Ahhhhhhhh Chicago!!! I just love it!!!!!!!

DEFINITELY make an attempt at a Cubs game- even if you are not a baseball fan, it's a great time. I will warn you that weekend games tend to be sold out, so you will have to scalp tickets... and depending on when you'll be here,who's playing, etc., this could get spendy.

A very cool jazz club to hit is The Green Mill, located in Uptown (4802 N. Broadway). Also, in Bucktown, which is very close to Wicker Park, you may want to have dinner at the Soul Kitchen (1576 N. Milwaukee)- noisy, fun, and great soul food!

I second the poster who suggested looking into summer fests- they are my favorite part of living in Chicago in the summer! I personally avoid the Taste, but being a local, I think I'm jaded. See if there are any smaller street fairs going on- these are much more fun (in my opinion)- live music, cool venders, cold beer! Can't beat it!
Enjoy!

Oh, one more suggestion- on Sundays, the House of Blues has a gospel brunch that you might want to check into!

As a local, I also have avoided the Taste of Chicago for years now, mostly because of the crowds and the fact that I can try any of the food whenever I want. The crowds, especially on weekend days and on the day of the fireworks, are enormous. That being said, you might find it enjoyable if you go at an off time during the week, as you will be able to taste quite a few different foods and have a chance that the food will still be the right temperature. The fireworks are held on the 3rd of July, they also usually have a free concert that day so the crowds are huge all day long. If you do go on the 3rd to see the fireworks, pick a spot early and don't end up near the food booths at the end or you'll end up in the huge human traffic jam.

One more thing, for a better link to the Taste of Chicago and festivals go to www.cityofchicago.org/specialevents and look under Festivals and Events or Neighborhood Festivals. I might have to go this year, one of my favorite performers is there.....

Lived for many years in Chicago and always loved Taste of Chicago. Going back this summer for the 4th and guess where we'll be! Wrigley Field and a wonderful old ball park and is it the Cubbie Bear, the bar that's near the park?

I forgot about the fireworks! Where should we go to find the best? And where should we camp out (specifically) to enjoy the sights? Michele