Visiting Chicago for a romantic weekend…
As for a hotel to stay in, the Drake, specifically a Lakeview Suite, which surprisingly is not that expensive. Or the newest of hotels in Chicago, the Hard Rock Hotel. It is out of the way, but they know how to treat a guest. If you are looking for something a little less expensive, but just as nice, there is always the Hilton Homewood Suites, off from Michigan Ave. and you can get a one-bedroom suite for a very reasonable price.
Activities,
Since you mentioned the “River ride” from My Best Friends Wedding, that is the Architectural Tours along the Chicago River. They are nice in late summer since the weather is always perfect. If you are interested in history/architecture it is a great trip.(http://www.chicagoline.com)
The Cubs games are always a little difficult to get tickets for unless you are willing to pay high price from a broker. It is well worth the price if you are a baseball fan. The experience of Wrigley field is one that everyone should experience once in their life. The Sox tickets are easier to come by. The new stadium is great, but has less of a “family” feel, but it is always a great evening at the ball park at Comisky.
As for shopping, that is the easiest. Michigan Avenue is the only thing your really need to know.
Restaurants with a romantic feel…
I would recommend someone visiting Chicago:
The Signature Room:
The restaurant sits at the top of the John Hancock has the most breathtaking views of the city.
http://www.signatureroom.com/TRU
A devotion to artistry is obvious at TRU, and it is reflected in every element of the restaurant. There's a small collection of vibrant modern artworks, including an Yves Klein sculpture that dominates the bar, a haunting Maplethorpe gelatin silver print that compliments the softer lines and lighter tones of the dining room, and a colorful Peter Halley painting that brings out the brighter and bolder ones.
Contemporary, innovative glass sculpture enhances the dining experience. The collection also includes an assortment of original glass surfaces, which are hand painted exclusively for TRU. That devotion continues in the meticulously prepared progressive French cuisine created by owners/chef Rick Tramanto and Gale Gand.
http://www.trurestaurant.com/Some tips for romance:
Sears Tower. The observatory atop of Sears tower can be a very romantic journey, as long as you go at night.
Ravinia festival:
“Open in 1904, Ravinia began as a way to get Chicagoans to ride the rails, and they've been pouring into Highland park every summer since. As North America's oldest music festival, Ravinia Festival presents internationally known classical, jazz, pop, children's music and dance companies, and it also serves as the summer home of the Chicago Symphony Orchestra. Amid Ravinia's uniquely convivial environment, you can experience crooners, Grammy-award winning popsters, blues-belting babes, queenly divas, retro rockers, world music giants, chamber jazz recitals and more. Pavilion seating offers a better view of performers, but many festival-goers prefer to celebrate the canvas of nature's colors and cool evening breezes right on the lawn. Spread the blanket, light some candles, unpack a gourmet picnic and fine wine and revel in some of the planet's best music under the stars.”
http://www.ravinia.orgIf you are coming late summer then there is always the Lyric Opera, which starts in September (http://www.lyricopera.org/home.asp), or there is usually very good theatre events to see (http://www.broadwayinchicago.com or
http://www.meetinchicago.com/rol/search.ht...tb&kw=THEATERS)A great site to find all that is going on in Chicago is
http://www.meetinchicago.com/index.htmHave a great time visiting Chicago!