The people are lovely...

I live 30 miles south of Chicago but often get downtown. It's a beautiful, world class city. Like many other big urban areas it has many areas that are not safe. Check with your hotel front desk for places to avoid. Transportation is plentiful though not cheap. Our museums are world class. The Art Institute is right on Michigan Avenue as is the Orchestra Hall -- home to a wonderful symphony which is considered by many to be among the world's best. Other fantastic places are The Museum of Science and Industry and the Shedd Aquarium (again one of the Nation's best). It is the lake, though, and the fantastic park system that bring out the true beauty of the city. Seeing the skyscrapers from the beach or a cozy blanket spread out on the grass in Grant or Lincoln Park is lovely. Shopping on the 'Mag Mile' (aka Michigan Avenue) ensures beautiful shops. Many designer boutiques can be found in the Gold Coast area. It is the people though who make the city of Chicago work so well. Talk to them. They're generally extremely nice. We are truly a melting pot that promises a wonderful hassle-free trip for women.
Rose, Illinois, USA

Lakeview is my favorite neigborhood. There is a big gay population living there, so the whole community is very open and inviting to any one of any kind. There are plenty of nice restaurants and bars to have a good time. One of my favorites is a really small ice cream and coffeshop called Bobtail's. Its right on the corner of Broadway and Wellington. Then if you walk up and down Broadway, there are plenty of restaurants, shops and bars. One of my favorites is Szechwan Garden. Andersonville is also the place to be for any traveling lesbians. It's considered to have Chicago's biggest lesbian community. It's very welcoming, charming and beautiful.
Amy, Chicago, USA

Safe hotel, jazz, restaurants...

My favourite place in Chicago is the Abbey Pub (http://www.abbeypub.com). They have great Irish music and good food as well. You can get there easily on public transport and the barman will be happy to call a cab to take you back to your hotel. The Club Quarters hotel in the Loop is excellent. It's close to Sears Tower, Art Institute, and Blue Line to O'Hare Airport. Wireless Internet is free throughout the hotel. I found the hotel safe for single women (111 West Adams Street, Tel: 312.214.6400)
Amy, Valley Glen, USA

A few years ago I went to Chicago for days days with two female friends. We discovered a non-smoking jazz club, the Jazz Showcase at 59 W. Grand Ave. and Clark St. It has been there for over 50 years. We felt comfortable there and heard some great jazz. We even walked home to our hotel (The Embassy Suites near Navy Pier). There are more condos in that area and there were lots of people on the street at midnight. Not the kind of people that would give you trouble! They also have a Sunday show at 4 pm.
Linda, Canada

I spent five days in Chicago attending two conferences. Two restaurants I highly recommend are: (1). Gibson's Steakhouse - famous people all frequent it --it's a classic (had delicious fish) (2) Le Colonial (French Vietnamese-- outstanding both in food and atmosphere) Both are on N. Rush Street just off North Michigan Avenue.
Iris, Montreal, Canada

I live in Chicago and have two restaurant recommendations: (1) Cellars Market -- the cafeteria in the basement of the Board of Trade building (141 W. Jackson Blvd.) is awesome. Expect good prices and great food just about anytime of the day (not sure of the hours but I've eaten there for breakfast, lunch and dinner). Best salad bar I have ever seen! Tel: 312.427.3444 (2) Kouks Vintage Cafe (5653 North Northwest Highway) If you are near O'Hare airport there is a really cute coffee/tea shop in the Norwood Park neighborhood. It's also a resale shop with amazing items and prices on vintage items and is really worth the trip. Tel: 773.594.8888
Amy, Chicago, USA

Restauraunts, theatre, chocolates, etc...

When recently visiting a friend of mine in Chicago, we stumbled on a fabulous little restaurant called "La Creperie," on Clark Street. Wonderful crepes, both savory and sweet, and they have other things, such as soups, as well. My friend and I split a savory crepe and then a sweet crepe for dessert, which was filling and inexpensive. I went around Bastille Day, so the owner (originally from France) was decorating the courtyard. A lovely place - I ended up purchasing a gift certificate over the phone for my friend and her husband as a thank you gift.

If you're a choco-holic, try out Moonstruck Chocolate Cafe on Michigan Avenue - lovely desserts, like the triple chocolate mousse cake, drinks like the Brown Cow (Chocolate root beer float) hot chocolate, chocolate truffles, candies and more. If you're more in the mood for a chocolate fondue, try Ethel's Chocolate Lounge (decorated like a cross between retro and a chocolate box). I went to the one on Armitage, but they're a bit of a chain - there are others around. Not nearly the variety of Moonstruck, but the chocolate fondue for $25 sated the three of us nicely.

Other great things to do: Go to the John Hancock building, and instead of going to the observation deck, go to the lounge, order a drink and sit and stare out at Chicago in miniature (I think the lounge is on the 96th floor) - during the summer, it was fun to see swimming pools the size of postage stamps. Buying a drink there costs about the same as going to the observation deck.

Chicago is a good theatre town as well (before Spamalot hit Broadway, it tried out in Chicago - my friends went 3 times!). There's the Goodman Theatre, the Steppenwolf and the Lookingglass - all well-known, well-regarded regional theatres. If you're into improv, you've hit the jackpot - try catching a show at the famous Second City (I think once or twice a week there's a show called "The Best of Second City") where the likes of Stephen Colbert, the Belushi brothers, Bill Murray and many, many more got their starts. There's also the Armando Diaz Experience, the Improv Olympics, and many other groups. There are also shows like Too Much Light Makes the Baby Go Blind at the Neo-Futurariam - 30 short plays in 60 minutes (if I'm remembering correctly) - you roll a die and pay $7 plus whatever you roll - if the show sells out, the audience gets free pizza.
M.K., New York, USA

Andersonville is my neighbourhood...

I'm glad that you asked about Chicago! I have lived here for 11 years and am still discovering great places to explore. My favorite neighborhood is located on the Far North side of the city and is called Andersonville. This area was originally known as a Swedish neighborhood, and there are still several
Swedish restaurants and stores, including the Swedish American Museum Center (5211 North Clark St.) and the popular (and crowded!) Swedish Bakery (5348 North Clark St.), but now the area is better known for being very gay-friendly and for having a large concentration of Middle Eastern stores and restaurants.

There is an excellent woman-owned independent bookstore called Women & Children First (5233 N. ClarkSt.), a cafe for travelers with great food and drinks, called Kopi (5317 N. Clark St.), and a number of different shops where you can buy handmade chocolates and other delicious baked treats. The area of Clark St. from roughly 5000 North to 5800 North has many interesting stores, restaurants, bars, and is a fun place to window-shop. This area of Chicago is extremely safe and you will see people walking around at all hours. It is easily accessible on the Red Line of the el and on the Clark (#22) or Broadway (#36) busroutes. A short bus ride or walk away is a woman-owned sex toy shop called Early to Bed (5232 N. Sheridan). Some of my other favorite stops in Andersonville are m.henry (5707 N. Clark St.) for brunch, Sunshine Cafe (5449 N. Clark St.) for inexpensive homestyle Japanese food, and the Hopleaf (5148 N. Clark St.), which has an astounding beer selection.
Sydney, Chicago, USA