Well, it's actually colder than Scotland in the winters.  As far as diversity goes, you have different minority groups compared to central London.  There are more people of Italian, Mexican, and Old European descent, unlike the Indian, Middle Eastern, and Eastern Europeans in London.  So, if you like deep dish pizza, beef, Mexican, Italian, etc., you'll enjoy the dining experiences.  There are some nice shops along Michigan Ave. a.k.a. The Magnificent Mile.  It's kind of like Knightsbridge and Sloane Square.  Nightlife will probably not compare to NY or even LA.  If you enjoy architecture, the downtown area has a vast array of different styles of modern architecture, lots of skyscrapers.  Depending on your interests, you should be able to find enough to keep your attention for a few days.  And, you might want to consider visiting the area in Autumn.  Summer is hot and humid.  Winter is dry and bitterly cold.  Spring varies depending on the rains.

I travel Chicago several times a year and it is a beautiful city.  Get there in warm weather (May-Sep) and the lakefront and Michigan Avenue and Gold Coast and gallery row and Lincoln Park and Wrigleyville and many other areas are wonderful visits.  The big difference between Chgo and other big U.S. cities (except maybe NY, SF and Boston), is that it's residential, and if you have just a few bucks (but not near-broke, lol) it's beautifully residential, and if you have a lot of bucks it's gorgeosly residential.  Shopping streets are in all the areas mentioned above plus many more (Mich Ave being the swankiest, but others have their own charm and are equally as diverse and safe).  Museums in central city area are excellent and nightlife in several areas is as good as it gets.  The panarama of the lakefront and skyline is unequaled in this country (sorry SF and NY, but Burnham's design of Chgo's public vs businesss access is the best protected big city plan around).  Center city events like Chicagofest and Jazzfest and others turn the lakefront into a carnival full of whatever type people and activities you could think of, and are safe and free and continuing throughout the warm months.  Neighborhood events just add to the mix, and because of Chicago's ethnic diversity, there is endless color and traditions to pick from.  Evening concerts in Grant Park and Centenniel Park, the ferriswheel and bars on Navy Pier, the green and boating activity at the various harbors, and neighborhood after interesting neighborhood make the city a walker's paradise.  The el (elevated and subway train) system reaches out in all directions from the loop (central financial district) and can whisk you almost anywhere.  The professional theatre is pretty good and the non-profit theatre world-class (matter of fact, reminds me of London in that respect).  Like any big city, there is a criminal element, but be smart and you'll be safe.  In all my visits there I have never had a problem, and I am a wanderer and have covered a lot of what is offered all over town.  I'm sure locals will write of much more on this board, as I could, but I think you get my drift.  Wonderful city.  

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BTW, having now opened your site link, I can assure you Chicago will love you same as you'll love her and us.  If I'm converting currency right, you're a bit above what I allow myself, but there are plenty here who will jump at what you offer.  I assume your reviews are good (no time now to look) and that you deliver with he best.  Ever want to spend the day just strolling, or run a special for us everyday guys in the States, just let me know.  Hell, I'm always good for another visit to Chicago, and you'd sure add to the skyline.

Assuming you stay downtown, near Michigan Ave., the city will offer you many events to plan your trip around.  Depending on your interests (and I gather from your site and your reviews, you are very cosmopolitan and will prefer unique experiences), you may want to search through our City of Chicago events calendar and find something a bit more off the typical big city venues.  Then book your visit.  I know you will not lack for companionship.  I do know I will try and schedule myself for a lunch/dinner date.  I think it would be great flirting with you in public in an interesting Chicago restaurant.

my friends would love to show you a good time in chicago

Most of my relatives from England find the shopping in Chicago incredibly cheap.  They say that the amount of money they save more than pay for the flights.  Of course, I'm sure you could say the same about any city in the States when compared to London.

Carrie,

After reading your reviews and seeing your pictures Chicago will offer you a tremendous amount of business as well as a great time in the summer. I hope you decide to visit, I don't think I could resist those legs.

The Magnifacint Mile ( downtown chicago )  Some must see museums,  Buckingham Fountian,  Wrigley Field, Oak Street Beach,  Navy Pier,  The Gold Coast - just to name a few off the top of my head.

I have visited your site on numerous occasions ( and in fact we have communicated by e-mail a few times ) I would love to see you visit Chicago..

Just a suggestion,  June and July are great months to be in Chicago..

RAY

Hmmm...my original response seems to have never been posted so I will try again.  Chicago is not going to be quite as metropolitan as London.  Where London has a great deal of Indian, Chinese, Middle Eastern, and Eastern European influences, Chicago has more Mexican, Italian, and some Russian Jewish influences.  As for restaurants, you should try some of the distinctly Chicago eateries, e.g. Lou Malnatis for pizza, Topolobampo for nationally renowned Mexican, and any of several steak restaurants.

For sightseeing, you have the Sears towers (tallest buildings), the John Hancock building (nice bar/lounge near the top), the Water Tower (survived the Great Chicago Fire), and Navy Pier.  In addition, there are numerous museums and activities depending on when you arrive.  I would suggest that you visit in Autumn.  Winter is bitterly cold even compared to Scotland.  Summer is not bad if you don't mind hot and humid.  Spring is a possibility too, but I think Autumn is better.

Shopping on Michigan Ave. a.k.a. the Magnificent Mile is similar to Knightbridge and Sloane Square in London.  Cars are not as well behaved as London though, especially towards pedestrians.  The nightlife will not compare to NY or even LA, but there are numerous clubs and venues, like the House of Blues.  You should have a visit if you get a chance.

Also, a fair number of women use RoomService 2000 for screening clients.  Law enforcement in Chicago can be somewhat annoying towards escorts.  You can check them out at www.roomservice2000.com if you are interested.

Chicago will have YOU to offer!

You're absolutely stunning!

Carrie,
I'm a native of the Chicago area, but I've encountered many people during my life who are transplanted here from elsewhere.  Most of them say that Chicago is the best of the big American cities.  

The lakefront is hard to beat.  Good museums, excellent dining, interesting neighborhoods;  you would find plenty to do.

I would welcome the chance to finally meet you.  

tennis