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For dessert, hands down Tru. I've been twice, and I love it. You have to call them specifically for their "dessert menu." Although it's only 2 courses, you also get a small amuse bouche, the two desserts, intermezzo of chocolate, the dessert cart, and something to take home. They'll also wrap stuff for you if you don't finish it. The last time I went, it was $25 (so aobut $35 with tax and tip) per person.
More food, Chicago-style pizza and hot dogs, Garrett's popcorn, Eli's cheesecake. I like Le Peep and Lou Mitchell's for brunch. At Lou Mitchell's you have to wait in line, no reservations. But you get donut holes while you wait!
For architecture, take the Chicago Architecture Society's boat tour. It is the best way to see the city.
The Chicago Greeter program is also good if you want a guide about a specific part of the city. When my FI and I did it, he did a general downtown tour, and it was great. You also get a one day CTA card with the tour, so that was cool too.
HTH!
I took an architectual tour by down the Chicago River by kayak which was a cool way to see the city too. Hard to get a lot of the info though so if thats what you are looking for, go with the boat tour!
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You must go to Lou Malnati's for pizza. Also Garrett's for some delicious cheese and caramel popcorn (weird combination BUT it is their best seller).
Some more restaurants: Buca di Beppo and Bandera (also blogged about by a Mrs. bee)
Try to fit Millenium Park into your visit. It's very relaxing and lots to see.
I love the Art Institute :) Chicago also has two of the nicest zoos, if you're into that sort of thing. Take a drive down Lake Shore Drive also if you get the chance, especially on a nice sunny day. I LOVE the contrast of the blue shimmering lake on one side, with the gleaming city on the other. If you like nature, venture over to Indiana and visit the Indiana Dunes National Park. It's also quite beautiful :)
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Definitly stop by Mellenium Park and get your token Bean picture (the Bean is one of my favorite touristy things - I love it). Also try and stop by Navy Pier if you've never been - the Ferris Wheel is definitly fun.
Hey! I'm not sure what week you're referring to, but just a heads up that Lollapalooza is August 7-9, so all the spots around Grant Park are going to be really crowded. I go every year -- I love Chicago, too. :)
@amysue
Thanks for the heads up! That IS the week/end we will be there. Yikes! Will it make everything more crazy? Travel included?!?
Thanks for all the suggestions!
Hey! The festival doesn't actually start til Friday. There will be several thousand extra people around, but the city is big enough that it can handle it. Just avoid the Grant Park area, especially by car (large crowds crossing the street), and you should be ok. And if there are any restaurants you want to eat at, be sure to make a reservation plenty in advance. Also, the festival gets out at 10 at night, and after that all 60,000 people pour out and head for the nearest bar/subway. The subways/buses are usually packed! So just be prepared.
I had some friends in town recently and we went to the Field Museum, which is fun in it of itself, but also the museum is located near Adler Planetarium and Shedd Aqaurium, all on Museum Campus and Northerly Island...which is just beautiful to walk around. You're close to the water but also the downtown Soup Loop.
Tapas Valencia is a great tapas restuarant. I also love Brazzas Brazilian Steak House...which is soo yummy, but you have to be willing to spend several hours there enjoying the food! Also Rosebud Trattoria on Dearborn is a lot of fun, and if it's nice out make sure you get a table outside!
Also, Gunthries in Wrigelyville is a super fun, low key bar with all sorts of fun board games and trivia games. Get there early before the dinner crowd to grab a table and play. You can order in food from anywhere to be delivered. When I had friends visiting we went to Gunthries and had Lou Malnati's Pizza delivered!
Also, if you're venturing out of the city for Architecture, make sure you stop in Oak Park, which is home to several Frank Llyod Wright homes, including one of his own residences and the home he built for his mistress, Mamah Cheney.
Have fun!
Must try Avec for dinner if you're a foodie! Bacon wrapped dates stuffed with chirizo is the one dish everyone orders! Prepare for a long wait on weekend nights (they don't take reservations). It's our favorite restaurant in the city (we're locals) and if you're a fan of Top Chef, it's Stephanie's (last season's winner) favorite Chicago restaurant (we've seen her there several times!).
A tip about Chicago's steakhouses ... many say that Gibson's is the best, but it also gets very busy. Hugo's Frog Bar is next door and run by the same people, and is normally much easier to get a table at (still busy though, so you'll need to book). They do excellent fish, but you can ALSO order steak there ... Gibson's steak!
Chicago-style pizza is gross (in my opinion), but most people say it's worth trying once ... then you can see for yourself that it's gross!
Second any of the Architecture Foundation tours - the river one is very relaxing if there's nice weather, but the walking tours are very good as well (and probably a bit more detailed). Plus you actually get to go inside the buildings.
Couple of great beer + food style places...
Hop Haus (kangaroo and ostrich burgers)
The Gage (near Millennium Park)
The Publican - haven't been to this one yet, but heard good things
If you're looking for a microbrew and restaurant, try Goose Island. Their beer is awesome, and they have a great restaurant with two locations--one on Clybourn and one on Clark near Wrigley Field. Not sure how far either place will be from your hotel, but it's totally worth a visit! And you can always tour Wrigley after dinner.
Hopleaf for drinks, Blackbird or May Street Market for dinner, Intelligentsia for coffee, and Tweet for brunch! I hope you have a fantastic time--this city is beyond amazing.
Absolutely, take a boat architecture tour. Amazing!
Carnivale is a fantastic restaurant with a great atmosphere. Highly recommended! But for a true Chicago experience, I would venture out of downtown and go into the neighborhoods. Wrigleyville is super fun, Lincoln Park is always great. So much good stuff!
For evening entertainment, Second City is always really fun.
Ooo, also, The Sears Tower (aka the Willis Tower...boo!) has a new observation deck called the SkyDeck that is glass all the way around. Even the floor. So if you're brave, definitely check that out. The views are supposed to be fantastic.
Have fun! Chicago is a FABULOUS city! :)
I echo Mrs Powederpuff in the Sears Tower skydeck.
Wrigleyville is also a blast!
I live about 5 miles from the Farnsworth house and it is worth the trip from Chicago IMO. I have been there a couple of times and it is pretty neat!
Powderpuff, we went to Carnivale for my friend's engagement dinner (about 25 of us) and it ROCKED!!! They have random guys on stilts wandering around (thats how huge the place is) and the food is divine (still dreaming of truffle fries...drool)...I def recommend Carnivale as a dinner place!
Everyone has already suggested some great ideas so far!
One of my fav microbrews that hasn't been mentioned is Piece Restaurant. It's a new England style pizza joint (I really hate deep dish) in Wicker Park/Bucktown that also brews its own beer, and it's SO good. Goose Island is pretty good, too, but I'm not a huge fan of their food.
I also second the person who suggested Avec and Blackbird for dinner if you're a foodie. I've been to both places for lunch, and it's been amazing!
The architectural boat tour is also highly suggested!
Wow, so many great suggestions! Have an awesome time!
Gerbera, I just wanted to say that I interviewed for a position at Focal Point HQ back in 2004... totally random. I didn't get the job tho, haha.
PS. Brunch is the best meal EVER, and my fave brunch spot is Meli Cafe in Greektown!
This is great! I'll be in Chicago from July 29-August 2! I've been before, and I LOVED shopping on Michigan Ave and loved eating at Gino's. Yummy. I can't wait to go back!
Thanks everyone for ALL the great suggestions! We'll definitely take them all into consideration!
@ Mrs. Emerald, small world!
@ August15bride, glad you can use the suggestions too!
Hi Everyone!
Thanks so much for all your great suggestions! We ended up having so much more free time than we all thought. A few of the things we checked out included Millenium Park, Renzo Piano's new wing to the Chicago Art Institute, the Gehry Pavilion, Magnificent Mile (no shopping! 
), Wrigley Field, Chinatown, Navy Pier, Hancock Tower, Robie House, Farnsworth House and so much more. We spent A LOT of time walking the city and suburbs...I honestly don't know which suburbs we walked through. 
We ate at A Mano, Harry Carry's, the Corner Bakery & Cafe, Phoenix Restaurant for Dim Sum (really good if you're local and looking to try a good dim sum place), Primehouse.
In short. I LOVED Chicago. I can definitely live there! It's got the big city that I want/need but yet it has the feel of a smaller city, if that makes sense. We loved all the public spaces and the cleaniless of the city was amazing. And Chicago's got the big Chinatown that will keep my mom happy! Hehe.
Thanks ever so much, again!
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Hello Hive!
Let me preface by saying, I LOVE my job. Through my job a coworker and I (wait for the best part) are going to Chicago the first week of August for a training seminar at Focal Point Lighting's Headquarter in Chicago. (wait for it) They are paying for our airfare, hotel and meals for Thursday and Friday (the days of the seminar) and through Sunday! Yup, they are paying for our hotels for the weekend as well. The best part? They are paying for the FI to come with and coworker's wife as well!!!
See. I do have the best job ever.
Anyway, so I know there are some Chicago-ens(??) buzzing around here. What are the tips? Must sees? Must eats?
We're foodies and architects looking for the many fabulous great architecture the fair windy city of Chicago has to offer. And of course what do YOU consider the best steakhouse in Chicago, by far? Best dessert? Best Sunday brunch? Evening entertainment? We'll be heading 2hrs outside of the city to see Mies van der Rohe's Farnsworth House - can't wait!
Almost forgot; best microbrew restaurant? Ya know it's a microbrewery but also has a onsite restaurant?
Thanks so much!
P.S. The best part is that we had initially planned a Chicago getaway before getting engaged. When we got engaged we cancelled the trip to save money. And now we get to go! For free! :)