This is one of my favourite cities. Chicago is clean, safe and there’s tons of “green” space. The waterfront is so well maintained. If you stay somewhere relatively central, you can walk just about anywhere. Public transit is very affordable and easy to use. Cabs are also easy to access... much more so than New York!
 
I usually stay either in the Lincoln Park district or right downtown.
 
Where to Stay:
The Beldon Stratford. One of my absolute favourite places. Across from Lincoln Park (part residential and part hotel), this beautiful old building has two great restaurants on the main floor, one of which is Mon Ami Gabi, a lovely French bistro. Many of the guestrooms are filled with antiques and the neighbourhood is amazing. The Lincoln Park zoo is directly across the road and it’s free. There’s also a great horticultural centre there.

The Drake. This is one of Chicago’s oldest grand hotels. It has a great “executive” bar in the basement, which serves excellent fish soup. Great location.

The Raphaello. A boutique hotel about a block from the Drake, it is just one block from the lake. Really nice. Recently refurbished.
 
 
Sightseeing:

• Architectural boat tour: One of the best things in Chicago
• Millenium Park: One block from the Chicago Art Institute
• Chicago Art Institute: Wonderful! Also has a lovely spot for lunch
• Shedd Aquarium: Absolute “must”
• Museum of Science and Technology: ideal for today’s kids
• Hancock Building: The top floor. Lovely at sunset

 
Where to Eat:
Via Oestra (State Street):  Great Italian Food served family style. Excellent value and always “packed” with people. Great “buzz.”  You must have a good appetite for this place

Shaw’s Crab House: Fun with great seafood.  Casual side and formal dining side
Viande (attached to Mariott) on Ontario Street: Very good value

Uno or Duo: Tasty deep dish pizza. Order the small!!!!!

Spiaggia (directly across from the Drake): The formal side is Barak Obama’s favourite place in Chicago and it’s very “high end dining.”  There is a café side that is much more affordable Lovely ambiance and view. Decent food

North Pond (in Lincoln Park):  Expensive, but very good. Chef Bruce Sherman uses local and organic ingredients

Aruun: Excellent Thai. Long cab ride. Very formal and quiet, but fabulous food
 
Food Shops

Fox and Obel: Fabulous specialty food store and market. A great spot for a quick bite

Voges: chocolates that are fabulous. It’s located in one of the shopping concourses on the Magnificent Mile

Garrett’s: Terrific gourmet popcorn. I have yet to purchase this popcorn. Everytime I go to Chicago… there’s a lineup!!!!
 
Shopping

• Magnificent Mile is an absolute must.
• Feline’s bargain basement is always fun and it’s great to go into all the luxury stores to look around.