Explore Chicago’s unique food, entertainment, and culture options with Stephanie Khattak.
As a travel writer, I visit nearly 100 American cities each year. It’s hard to pick a favorite, but Chicago is easily a top choice! This wonderful city is one I return to again and again to see friends, take in the sights, and soak up its unique history; diverse, international dining scene and world-class culture.
My most favourite thing about Chicago is how friendly it is for such a large city. Rather than being overwhelmed by its size, I find myself inspired by the many interesting experiences available to choose from, and how accessible those experiences are, even for those who may be only visiting the city. Walking among its skyscrapers or throughout its neighborhoods, it’s easy to feel a sense of discovery, and also right at home.
Chicago is a culturally rich Midwest metropolis, and its diverse local food scene, top entertainment talent and friendly neighbourhoods are hard to beat! Air New Zealand flies non-stop from Auckland to Chicago, making for an experience that is efficient as it is unforgettable, whether you’re visiting a local or just vacationing like one.
Immerse yourself in Chicago’s amazing art and history before even unpacking your bags! The 21C Museum Hotel features an awe-inspiring collection and rotating exhibitions that engage travellers and locals alike. Book a personal onsite art tour for a truly special experience or take a short walk to the neighboring Museum of Contemporary Art Chicago.
The Palmer House Hilton, on iconic State St in downtown Chicago, is an elegant choice. One of America’s longest continually running hotels, it has been operating for more than 150 years. While its ornate decor reflects its original design, modern updates make for a comfortable stay.
What do Tina Fey, Jordan Peele and Bill Murray have in common? These comedy greats all started on Chicago stages. For generations, Chicago has been one of America’s best places to catch rising stars. Check out open mic night at The Green Mill or laugh with locals in a casual, neighbourhood pub atmosphere at Timothy O’Toole’s. Want to test your own skills? Take a drop-in class at legendary comedy incubator The Second City.
Chicago’s architecture is as accessible as it is beautiful, and much of this local history can be found in the walkable city centre.
The Chicago Cultural Center was completed in 1897 as Chicago’s first central public library, and it features luxe architectural materials as well as the world’s largest stained glass Tiffany dome. The Center’s exterior is just as enticing, with “Rushmore, 2017,” a colourful mural by acclaimed American artist Kerry James Marshall. Explore the space on your own, reserve a guided tour or take in one of its regular free public lectures, film screenings or concerts.
A short walk away and just across the Chicago River, the Chicago Water Tower was built to hide simple city infrastructure, making its intricate Gothic Revival design not only beautiful, but useful. One of the only structures left standing after the Great Chicago Fire of 1871, the building represents Chicago’s resilient spirit.
Chicago is known as a hot dog and deep-dish pizza town for good reason — great options for both can be found throughout the city! But Chicago’s food scene offers much more to enjoy, especially when you leave the beaten path.
Logan Square neighbourhood favourite Daisies does double-duty, serving up innovative pastries and coffee in the mornings and a farm-to-table, locally sourced dinner menu that features house-made pastas, seafood, and vegetables.
The Bongo Room offers outrageous brunch fare like Banana Red Velvet Pancakes and hearty breakfast sandwiches, and its Wicker Park location makes a great mimosa stop before hitting neighbourhood boutiques.
Award-winning Obélix brings a modern take to French bistro cuisine for brunch and dinner service in River North, and its dishes range from traditional to truly innovative, with a wine and cocktail selection to match.
Many of Chicago’s best finds are in its neighbourhoods, easily accessible by public transportation, cab or rideshare. Busy sidewalks, eye-catching architecture and vibrant businesses make them a comfortable option for exploring off the beaten path.
In Andersonville, try Lost Larson for pastries like cardamom buns, classic Danish Tebirkes and lingonberry almond cake. Enjoy a drink, browse the shelves and get inspired at The Understudy, a cafe and theatre-themed bookstore. Andersonville’s local shops, situated between Clark St and Foster Ave offer clothing, jewellery and vintage and handmade items. Pop into the Swedish American Museum and learn about Nordic culture and influence in the U.S. and beyond.
Logan Square’s picturesque Chicago Greystone townhomes line its main thoroughfare for an “only in Chicago” vibe. The Logan Theatre, a 1910s-era movie house, is still operational today, showing first-run movies and classics. Table, Donkey and Stick offers a unique selection of beer, wine and spirits inspired by the eating and drinking traditions of the Alps. Explore nearby Humboldt Park, one of the city’s most beautiful spaces, with a landmark field house, inland beach and historic lagoons.
Chicago is a big, friendly city with much to see and do, and with many local highlights to explore. With non-stop flights from Auckland to Chicago, Air New Zealand makes it easy to return to your own favourites in the city and find many new ones!
Air New Zealand flies non-stop from Auckland to Los Angeles, San Francisco, Chicago, Houston, Honolulu, and New York. Connections are available from Air New Zealand serviced domestic airports.
Book flights to the USA with Air New Zealand.
By Stephanie Khattak