Checkout Michael Jordan's store downtown Chicago and then head out to a Bulls game.
See Chicago on a beautiful day from Millennium Park, Grant Park, The Bean!
On a fine day, walk out to Adler Planetarium and look back at Chicago. It's a stunning view of the Windy City.
If you have a spare day in Chicago, take a walking tour. Very informative and worth it for a quick visit. About USD $25 - Just google Chicago walking tours, heaps of options!
Get a different view of the city by taking a guided kayaking tour up the Chicago River. Then once you've worked up an appetite get your hands on a classic Chicago deep dish pizza!
Grab a Giordano's pizza... Pizza will never be the same again.
Go up to the Signature Room bar at the top of John Hancock Tower at night, sip on a martini or two and savour a sweeping 360 degree view of the city and the lake.
Get out on The Ledge, if you dare. Step onto the glass viewing balcony on the 103rd floor of the Willis Tower in Chicago, the tallest building in the Western Hemisphere.
Go see the Chicago Cubs play at Wrigley Field. With a famous Chicago Hot Dog.
Fall in love with jazz at the Green Mill in Chicago.
Visit Millennium Park and see the Bean, take the architectural riverboat tour, bicycle by Lake Michigan, Lincoln Park zoo (lots of animals never seen in NZ and best of all, free!)
Go to the Chicago Cultural Center! It's free to get in. It's the old Chicago Library, and the building is absolutely stunning. There is a huge Tiffany Glass Dome. Totally photo-worthy.
Rock out at one of the best Hard Rock Cafes. Just a few blocks from Magnificent Mile in Chicago, this spot has brought live music & classic American food to the city for more than 30 years.
Spend a night in front of the ice at the United Centre, Chicago, watching the Blackhawk's, the home team, in some bone crunching ice hockey action.
Eat and drink your way through Chicago's vibrant restaurants and bars, and while you're there take a phenomenal river cruise to take in the historic architecture!
If you're in Chicago you have to make a trip to see Cloud Gate and see yourself in it. It's the centre piece of Millenium Park and is more commonly known as 'The Bean' because of it's shape.
If you have kids you gotta get them to the Rainforest Cafe in Chicago. The whole restaurant is built to look like a jungle and caters specifically for kids fun - but it promises a wild time for all.
If you like a good garden tour, you gotta take a stroll around the Crystal Gardens. A six-story glass atrium with over 80 live palms and spectacular views of lakefront Chicago.
You've gotta admire the work at Art Institute Chicago. It's one of the oldest and largest museums in the United States with over 300,000 works of art including the iconic American Gothic by Grant Wood.
You gotta take a ride on the Chicago river's "First Lady" Architecture tour through the city, followed by lunch and a beer on the riverside. Great stuff!