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Favorite romantic place to eat: Sola (http://www.sola-restaurant.com/) It's off the beaten path, but most places downtown that you might think of are too touristy and/or crowded to really be truly romantic. Plus it's right off the el.
As for things to do ... Chicago in June is fantastic. I would definitely consider tickets to a baseball game if you are fans. Rent bikes or rollerblades and hit the lakefront (or run if you are runners) because EVERYONE will be out. Go to Shedd Aquarium, and at least one other museum. The chicago architechture boat tour is a favorite (going down the chicago river). And if you're really adventurous you could kayak the chicago river.
I love this Italian placed called Prosecco. If you go for dinner, each meal is started with a complimentary glass! I'd also recommend checking out the Hancock Building viewing deck, but the best way to see the city is via a Double Decker bus tour. There are always tons of deals for couple's massages, too, so sign up for notices from Groupon or Living Social so you don't have to over pay for those luxuries while you're here. 
I suggest the Signature Room! Great view of the city from up there :)
I agree with the Signature Room but only for drinks and not for dinner. Therefore, instead of just paying admission to head up to the John Hancock observatory, you get a cocktail! This is a fun way to end a marathon shopping trip on Michigan Ave.
I also second the architectural boat tour. It's a great way to see the city. Check out the museums and pick the one that best suits your tastes.
One of my favorite romantic restaurants is Piccolo Sogno. Their outside garden area is so beautiful. You almost forget you're in a busy city!
If you are baseball fans and the Cubs are in town, that's always a good idea. Also, if you're the type that likes a few cocktails, it's fun to go to a game and then bar hop along Clark St. There will be tons of people out having a good time. Although, I have to warn you, if crowds and excess drinking aren't your thing, stay away!!!
Let us know what you decide and we'll try to help you out more!
If you travel a little bit north there is a place in milwaukee that is called Pieces of Eight it is right on the lake front.
There is also Kirsh's in Lake geneva.
Lake geneva is about an hour and a half north of chicago but a beautiful location that is visited by many who are in the chicago land area. check out lake genevas website
My fiance and I love La Creperie (http://www.lacreperieusa.com/) and Cafe 28 (http://www.cafe28.org/). Both have patios that will be awesome in June. The former is a cute little place in East Lakeview, and the latter is a Cuban Mexican fusion place in Ravenswood. If you're looking for music after dinner while on the northside, hop a cab to the Green Mill. It's an old Al Capone hangout with fabulous live jazz. During the day, rent a couple of bikes and ride up the lakefront!
I second Piccolo Sogno's patio - its beautiful and the food delicious. North Pond is my favorite romantic restaurant. It is a little pricey, but the view and the food is amazing. The restaurant, North Pond, is located in Lincoln Park and over looks the north pond as well as the downtown skyline. And the only way to get to the restaurant is to walk through the park. If you do go to North Pond, make sure you ask for the front room - that is the space that has windows facing downtown and the pond.
Top choice: North Pond (in the middle of Lincoln Park-- great location, excellent food, and they put your name on the menu, to keep!)
But, I also love Sola, David Burkehouse (for steak), and if you're looking for something off the beaten path Boinsoiree.
Also, @future.mrs.campfield: just as an fyi, Pieces of Eight closed a couple of years ago-- it's now Harbor House, a Bartolotta restaurant.
If you like fondue, I find Geja's Cafe to be very romantic. My boyfriend and I went there with my family for new year's eve, and again a few weeks ago. It's mostly candlelit in there, and a live guitarist plays classical guitar music. I love it.
As for stuff to do, all the usual attractions are my faves. I'm especially a fan of the Shedd Aquarium and the Field Museum. And for outdoor stuff, I love wandering around Millenium Park, Navy Pier, and Brookfield Zoo.
Oh and you didn't ask for nightlife, but in case you're interested, bf and I like Hub51 (bar, restaurant, and separate club area), Excalibur (just basically a giant club), English (restaurant and pub). and State (bar).
Enjoy your time in Chicago!
If you're interested in seeing the museums, look into buying a go chicago card or a chicago city pass, it will save you quite a bit if you want to be able to go to all of them...my favorites are the Museum of Science and Industry and the Shedd Aquarium...and visit the Skydeck ledge for lots of cool pictures
Also, try to stop at the Wit hotel bar for a drink. It's on the rooftop of the hotel-- very swanky.
Grand Luxe on Michigan Avenue is my very favorite place to go! It's fancy and delicious! And it would be really sweet to get one of those horse-drawn carriage rides for a beautiful June night!
Don't forget Navy Pier... every Saturday and Wednesday there are fireworks. It would be great to have dinner on one of the cruise ships and watch the fireworks on the lake!
Definitely second Noth Pond! It is absolutely a one-of-a-kind experience. Go early and walk around the pond and get some cute pics :)
Boka is also off the beaten path and super romantic, but still hip and fun (Sparks and I got engaged after dinner there!). It's a little expensive, but worth the experience (they have the BEST cocktails).
If you have time to do a Sunday brunch, please, PLEASE make a reservation at The Publican! It is the best brunch I've ever had in the entire world. Seriously.
Also, don't forget to hit up Millenium Park and get a picture in front of the Bean! There's a great restaurant across the street called the Gage, which has a great patio. It's also right by the Art Institute, which you have to see!
If you like comedy shows, definitely go to Second City. So many people (Bill Murray, Mike Meyers, Stephen Colbert) got there start there, and the main stage shows are hilarious. Go to Adobo before hand for the best margaritas and guacamole you will ever have!
The Old Town Art Fair is 6/11-6/12 and it is AMAZING. (http://www.oldtowntriangle.com/fair/general_information/index.html)
And Taste of Chicago starts on 6/24 (a little crowded, but very fun!)
Definitely do the architecture boat tour, and if you time it right, you can see the fireworks they shoot off Navy Pier every Wed. and Sat. night. Or, if you are really adventurous, you can do a sunset or firework kayak tour (http://www.kayakchicago.com/tours/fireworks-paddle/) It is SO MUCH fun.
:) Have so much fun!!! Chicago in the summer is the best city in the world!
Chicago in June is awesome. Look up choosechicago.com for info on what's happening around the time you're coming. There will be tons of neighborhood festivals going on by then which are fun and a little off of the tourist path. The Double Decker tour is another cool way to see the different hoods too, they all have their own personality, so it's worth exploring if you have time.
I second Geja's if you like fondue. It's super romantic, and if you sign up on their email list they will send you coupons and updates from time to time. If you like Middle Eastern there's Cafe Casbah, which is a BYOB (there's a liquor store across the street) and delicious. It's north of downtown on Broadway, in Lakeview , and there's lots of places to walk around and explore up that way.
Also, if you are a fan of live music Chicago has an awesome music scene. No matter what your taste is there is a venue from dives to schmancy clubs to see a band. Obviosuly there's a ton of blues, but there's some really cool Jazz (Green Mill) and rock (Empty Bottle, Double Door) too. Go on Yelp and type in what you're looking for and you'll find reviews on most places.
@ruby26: Those are Daddy Giraffe's fireworks! Everybody go see them :-D!
@misssparkler: beat me too it, but I second getting a photo with The Bean! It's so Chicago and I love it! The Bean is pretty close to the Art Institute which has soooome amazing works in it! The Impressionist section is to die for!
Cite! Such a beautiful view, excellent food, romantic. This is where my fiance proposed . If you go in the evening and plan yourr meal around the right time, you can also see the fireworks at navy pier!
Agree, Navy Pier Fireworks. The W Hotel lobby lounge bar is super swanky and romantic. Violet Hour in Bucktown is very romantic. Movies in the park is also fun. Bike riding along the lake front. They also have twilight boat cruises.
I love Chicago and everyone else's suggestions and I live here :)
@krystallite:there's a groupon for Cite!
http://www.groupon.com/deals/cite-restaurant-chicago-1?c=all&p=10
OP, keep checking groupon for chicago specials! that's what i do whenever i go out of town!
My new go-to recommendation is Henri. AMAZING!!! It's right across from the park on South Michigan Avenue. Gorgeous interior, impeccable service, and outstanding food. LOVE LOVE LOVE!!!
Here's my list of favorite meals in Chicago. Most are off of the beaten path and so amazing: http://www.yelp.com/list/best-meals-ive-ever-had-chicago
Okay ladies, it's getting close.... overload me with recommendations!! :) and thank you to all the ones I've been given already!
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things to do. We're taking our "mini-moon" there in June I think. I would LOVE suggestions!