5. TAKE THE MIDDLE ROAD
Stephanie Izard's Chicago restaurants hit the sweet spot between haute cuisine and cheap eats. Izard,known as the first female chef to win Bravo's Top Chef title,is the proprietor of wildly popular Girl&the Goat. There you'll find well-priced and scrumptious plates such as wood-fired branzino with green papaya salad. Also in the Izard empire:Little Goat,serving upscale diner food and all-day breakfast,and Duck Duck Goat,showcasing Asian-inspired dishes perfect for sharing. Seegirlandthegoat.com
6. CHEER ON THE HOME TEAM
Chicago is a sports town and here the devoted worship of baseball culture borders on the religious. To fit in with the crowd,don a Cubs team cap and shirt,and learn the words toGo Cubs Go. Cold beer and Vienna beef hot dogs are a must at Wrigley Field,plus you'll find Giordano's deep-dish pizza,peanuts,pretzels and more. Diehard fans start the celebrations early with buckets of beer,Buffalo wings and deep-fried pickles at one of the stadium's surrounding bars. SeeMLB.com
7. STAY AT THE PENINSULA CHICAGO
Located on the Magnificent Mile,within the city's premier shopping district,the 339-room hotel offers an unsurpassed level of service and attention to detail. The latest addition to the Pen's collection of restaurants and bars is the rooftop Z Bar,an elegant and inviting space where servers are dressed in Studio 54-inspired outfits and the views over Michigan Avenue are unmatched. Expect elevated bar food such as daikon frites and tater tots stuffed with bone marrow and Bordelaise. Seepeninsula.com/chicago andzbarchicago.com.
8. WALK THIS WAY
Architecture tours are popular in Chicago,and none more highly recommended than those offered by Chicago Architecture Centre (CAC). Join the 90-minute Historic Gems walking tour to explore downtown and admire soaring skyscrapers and ornate art deco masterpieces,while learning the stories behind them. With more time,venture further to explore Frank Lloyd Wright's creations and understand his impact on the city,where he lived for the formative first 20 years of his stellar career. Seearchitecture.org
9. FLY DIRECT FROM AUCKLAND
Air New Zealand will launch a new non-stop service between Auckland and Chicago's O'Hare International Airport from November 30. For Australian travellers,that means a new,convenient one-stop way to access this exciting destination. Business Premier passengers and other eligible travellers will be able to enjoy Air New Zealand's signature lounge at Auckland International Airport. The 15-hour flight is a great opportunity to test out Air New Zealand's Economy Skycouch or Premium Economy cabins and award-winning service. Seeairnewzealand.com.au
10.GROOVE TO THE BEAT
There's something for every kind of music lover in Chicago,though jazz and blues fans are extra spoilt for choice. Andy's is the place to go for late-night jazz seven nights a week. The cocktails are good and strong,while the menu features American classics. Over at Buddy Guy's Legends,don't be surprised to see Buddy himself jamming on stage. The blues guru was ranked byRolling Stone magazine as one of its 100 greatest guitarists of all time. Seeandysjazzclub.com andbuddyguy.com
11.RISE 94 FLOORS
For the best views of Chicago and beyond,get high. The 360-degree Observation Deck on the 94th floor of the John Hancock Building affords fabulous views by day and night. Thrillseekers will get a kick out of the TILT Experience,dubbed Chicago's highest thrill ride. An enclosed moving platform tilts riders out from the 94th floor (more than 300 metres above the ground),testing the mettle of participants as it tilts lower,then lower again. See360chicago.com
12.GET YOUR KICKS
A sign in downtown Chicago proudly marks the beginning of Historic Route 66,America's most famous highway. Pose for a happy snap and don't be surprised to see a few Harley Davidsons or classic cars getting revved up for the 4000-kilometre cross-country ride that ends in sunny California. Fun fact:Route 66 is also known as the Main Street of America,or Will Rogers Highway. Seeenjoyillinois.com
13.EXPLORE BEYOND DOWNTOWN
Similar to cities like Los Angeles and New York,Chicago is made up of diverse neighbourhoods. Head south of downtown to Pilsen,a cool area of vibrant street art,vintage shops and authentic Mexican food. Arrive early or expect to queue for legendary breakfast tacos and delectable rice-and-beans at Taqueria Casa Del Pueblo. Nearby,the National Museum of Mexican Art is a treasure,with free admission and a top-notch gift store. Seenationalmuseumofmexicanart.org
14.CHANGE YOUR PERSPECTIVE
Chicago River flows through the middle of downtown and along its banks are located many of the city's most impressive buildings. Hop on one of the many architecture cruises available,sit back and take in the cityscape at a relaxed pace. For a more exclusive experience,the Peninsula Chicago's Keys to the City program has partnered with First Lady Cruises to offer guests access to luxury small-vessel cruises,narrated by docents from the Chicago Architecture Foundation. Seecruisechicago.com,peninsula.com/chicago
15.SMILE FOR THE CAMERA
Search #chicago on Instagram and a stream of images appears featuring a reflective stainless-steel structure. Known to all as the Bean,the enormous shiny landmark's official name is Cloud Gate. Designed by Indian-born British artist Anish Kapoor,the public artwork has become a favourite backdrop for selfies and holiday happy snaps. In nearby Millennium Park,Crown Fountain is an interactive video sculpture that playfully spurts water at onlookers. Seecityofchicago.org
16.BROWSE 300,000 ARTWORKS
The Art Institute of Chicago is the second largest art museum in the US,second only to the Met in NYC,and boasts a collection of more than 300,000 works of art. Entry to the permanent collection is free. A new glass-and-steel wing designed by starchitect Renzo Piano is a striking contrast to the grand beaux arts facade,which has welcomed visitors since the institution opened 140 years ago. Seeartic.edu
17.ROCK OUT AT LOLLAPALOOZA
The annual summer music festival is known for its impressive lineup of metal,punk rock and alternative rock artists – The Cure,Nine Inch Nails and Eminem have all performed – though it also attracts more mainstream performers such as Beyonce and Coldplay. Summers in Chicago can be scorching,so best advice is to book a hotel within walking distance of the Grant Park festival grounds and take frequent nap-and-swim breaks to cool off and revive. Seelollapalooza.com
18.ADMIRE THE GRANDEUR
The breathtaking Tiffany vaulted ceiling is the crowning jewel of Chicago's historic Macy's on State Street. It was built in 1893,at a time when shopping was an elegant social outing and not something undertaken online while wearing pyjamas. Composed of 1.6 million pieces of glittering glass,it is the largest Tiffany mosaic in existence. The store's Walnut Room restaurant,dating back to 1905,serves satisfying American fare in an upscale environment featuring a grand marble fountain. Ask at the information desk about special discounts and tax-free shopping for international tourists. Seevisitmacysusa.com
19.WALK THE MAGNIFICENT MILE
Chicagoans are proud of the upscale stretch of North Michigan Avenue between the Chicago River and Oak Street,dubbing it the city's answer to the Champs-Elysees. French accent or not,it's home to many impressive historic buildings,luxury stores,fine hotels and elegant street art. It gained its magnificent moniker in the 1940s from a real estate developer,and it stuck. The mile ends at Oak Street Beach. Wait,what? Is Chicago a coastal city? No,while it is decidedly inland,there are more than 20 beaches along the shores of freshwater Lake Michigan. Seethemagnificentmile.com
20. DRINK TO SUE THE T-REX
The Field Museum of Natural History's most famous resident inspired the creation of a dry hop lager,Tooth&Claw,which is available in the museum's cafe. Also on the menu,Cabinet of Curiosities,a White India Pale Ale. The Field Museum is located at Museum Campus,an expansive park alongside Lake Michigan. A visit can be paired with nearby Adler Planetarium and Shedd Aquarium. Don't miss the Maori Meeting House,Ruatepupuke II,a 19th-century tribute to the Maori ancestor who brought the art of woodcarving to the world. Seefieldmuseum.org
Kristie Kellahan travelled to Chicago as a guest of Air New Zealand. The airline will launch a new non-stop service between Auckland and Chicago's O'Hare International Airport from November 30 this year. Seeairnewzealand.com.au