Exploring the Windy City: The Best of Chicago

First published in 2020. Some venues have since changed, and the text notes where.

The great city of Chicago, or the "Windy City" as it is dubbed, straddles the shores of Lake Michigan and is famous as a world-class destination. It has a vibrant arts scene, plenty of cultural attractions, top-quality shopping, great restaurants, a fascinating lineup of contemporary and historic architecture, and plenty of five-star and boutique hotels. And for first-timers visiting the city there are plenty more surprises in store, including experiences unique to the city, whatever time of year you visit, from sunbathing on the Lake Michigan beaches in summer to ice skating in winter. So what can you expect? Here are the top things to see and do, followed by where to eat, drink and stay.

Visit a museum

Lovers of art and history should definitely put a visit to the Art Institute of Chicago, located on South Michigan Avenue, on their lists. It's a world-class museum with a diverse collection of over 300,000 artworks spanning thousands of years. It's also arguably most famous for a collection of impressionist and post-impressionist paintings by artists including Georges Seurat, Renoir and Claude Monet. Also on any art lover's list should be a stop at the Museum of Contemporary Art, which is home to one of the largest collections of contemporary art in the United States, and a venue for cutting-edge exhibitions and touring shows.

At the north end of Jackson Park on South Lake Shore Drive is the Museum of Science and Industry, which is believed to be the first museum in the United States to incorporate the idea of "hands-on" exhibits. It has a mix of permanent and changing exhibits, as well as a theatre. On Museum Campus, the Field Museum's collection runs to millions of artefacts from the worlds of geology, botany, zoology and anthropology, and it's also home to "Sue", one of the largest and most complete Tyrannosaurus rex skeletons ever found.

Hang out at Navy Pier

Originally opening in 1916 as a shipping facility and amusement area, today Navy Pier is an imposing site located on East Grand Avenue. One of Chicago's most popular tourist destinations, it is home to 50 acres of gardens, attractions, shops, restaurants, concert venues and parks. Highlights include a huge Ferris wheel, now the Centennial Wheel, and a historic carousel in Navy Pier Park, and catching a performance at the Chicago Shakespeare Theater. When this article was written the pier also had a 3D IMAX theatre, which closed permanently in 2021, and the stunning Crystal Gardens, a six-level indoor botanical garden; its palms have since been removed, and the space now hosts temporary events. Navy Pier is also the home of many annual festivals and events, including summer fireworks, and if you happen to be in the city to celebrate July 4, the fireworks are spectacular. Navy Pier is also the departure point for a number of sightseeing tours on the water.

Unique selfie spots

Millennium Park is part of Grant Park, located in downtown Chicago, and a major attraction, and photo op, is taking a selfie in front of the huge Cloud Gate sculpture. It has a highly polished stainless steel surface which reflects the buildings, the sky, and visitors who walk through its central arch. There are also other things to do in Millennium Park, which include catching a performance at the Frank Gehry-designed Jay Pritzker Pavilion in the summer, taking a stroll through the serene Lurie Garden, or ice skating in winter on the McCormick Tribune Ice Rink. Another great selfie opportunity is in front of the gorgeous Art Deco Clarence Buckingham Memorial Fountain in Grant Park. Built in 1927, the fountain is one of the largest in the world and is surrounded by four seahorses representing Lake Michigan's four bordering states. During the day, on the hour, the fountain shoots 15,000 gallons of water through nearly 200 nozzles each minute to create an impressive display; after dusk, the water show is accompanied by amazing lights.

Tall buildings with a view

The 110-level Sears Tower on South Wacker Drive, now called the Willis Tower, was the world's tallest office block until 1998, when the Petronas Towers were completed in Kuala Lumpur. To this day the view from atop the Willis Tower is jaw-dropping; on a clear day you can see for kilometres across four states, as well as enjoy a bird's-eye view of Chicago's impressive architecture. The tower is about 442 metres tall, with an observation area called the Skydeck located on the 103rd level. If the normal view isn't enough, there's a glass box with a glass floor, called the Ledge, which juts out from the Skydeck, allowing visitors to stand and look directly down at the city below.

Another building with a view to put on your list is the former John Hancock Center, now officially 875 North Michigan Avenue. On the 94th level, 360 Chicago is a glass-walled observation deck offering views over Chicago's skyline and beyond. It also has an unusual feature, "Tilt", where a glass enclosure leans outwards from the building at an angle to give visitors a unique view of the Magnificent Mile from more than 300 metres above.

Go for a long walk

Michigan Avenue is one of the most attractive boulevards in North America, and the Magnificent Mile is a slice of it stretching north of the Chicago River, ideal for strolling, sightseeing and people-watching. Dubbed "the Rodeo Drive" of Chicago, it's home to an impressive lineup of galleries, boutiques and luxury shops, including many major flagship stores, along with attractions including the John Hancock Center, the Wrigley Building and the Tribune Tower.

Another great place to walk is Lincoln Park, Chicago's largest park and a nine-kilometre-long stretch of green straddling Lake Michigan. It is also home to the Lincoln Park Conservatory, the Lincoln Park Zoo, the Peggy Notebaert Nature Museum and the Chicago History Museum, along with playing fields, bike trails, jogging paths and beaches.

The Chicago River runs through the heart of the city, parallel to the lakeshore, and is famous for a large number of movable bridges: 18 in a stretch of just over three kilometres. The Riverwalk, which is great for a long stroll, has plenty of places to eat and hosts special events throughout the year, as well as being a departure point for river tours and cruises. Meanwhile the paved Lakefront Trail, which begins at 71st Street, stretches for nearly 30 kilometres and offers wonderful views of the city skyline, Lake Michigan and its beaches. Many of the city's top attractions are also located along the trail, including Navy Pier, Lincoln Park and Soldier Field.

And finally, The 606, also known as the Bloomingdale Trail, is a stretch of around four kilometres of abandoned elevated rail line which has been converted into a pedestrian path connecting Logan Square, Humboldt Park, Bucktown and Wicker Park. It's a great place to walk, jog, or explore by bike.

Other attractions

The Shedd Aquarium is located on Museum Campus, and is home to thousands of aquatic creatures from around the world, including otters and a giant Pacific octopus. The gigantic Caribbean Reef exhibit, where tropical fish swam through a huge aquarium, was replaced in December 2024 by a new centrepiece, Wonder of Water. Shedd has also offered the unique experience of a face-to-face encounter with a beluga whale, although these encounters were listed as temporarily unavailable in September 2026, so check before you go.

Also on Museum Campus is the Adler Planetarium, a place to explore astronomy and astrophysics, as well as enjoy yet more amazing views of the Chicago skyline. It's also the place to learn the history of US space exploration. You can view the tiny Gemini 12 capsule, which took two astronauts to space and back, in the "Mission Moon" exhibition, and catch a movie at the museum's Grainger Sky Theater.

The Garfield Park and Lincoln Park conservatories are very romantic places. A favourite place for locals, the Garfield Park Conservatory is one of the largest of its kind in the country, filled with plants, flowers and trees, and a haven from the hustle and bustle of the city. It's also a great place to take a break from the cold during the winter months. Lincoln Park Conservatory, in particular, allows access on foot directly to the Lincoln Park Zoo, which is exquisite and small.

Attend a major sporting event

Chicago is many things, including a city where sport is taken seriously. Just a few of its key teams include the Chicago Bears in American football, the Chicago White Sox and Chicago Cubs in baseball, and the Chicago Bulls in basketball. While obtaining tickets for American football and basketball can be tricky, there are usually more options when it comes to baseball. The finest ballpark in the city is Wrigley Field, home to the Chicago Cubs, which was built in 1914 and is the second-oldest Major League Baseball park in the US, second only to Fenway Park in Boston. This famous sporting arena has seen some legendary moments in baseball history, including the 1917 no-hitter pitching duel between the Cubs' Jim Vaughn and the Reds' Fred Toney, and Babe Ruth's "called shot" during game three of the 1932 World Series. Ballpark tours are conducted in season if you are curious, but it's much more fun to visit on game day instead and catch a game with the locals.

Go shopping

The USA, and Chicago in particular, offer Australian shoppers a lineup of great stores and great products to bring home. Top of the list, especially if you don't have much time, is the Magnificent Mile, or Mag Mile, located on Michigan Avenue between the Michigan Avenue Bridge and Oak Street. It offers a lineup of department stores, shopping malls such as The Shops at North Bridge, and big-brand, high-end boutiques. The famous Oak Street is a great place to combine shopping and cocktails, as well as offering a more tranquil shopping experience. Dubbed the Magic Mile, it's located close to Michigan Avenue at the Gold Coast, and is the place to browse among a wide range of designer boutiques, from Giorgio Armani to Prada. The shops of Lincoln Park are also worth checking out, particularly if you are into up-and-coming designers, and for fashionistas, Bucktown and Wicker Park have most of the big names of the fashion arena, as well as being a cool, artsy neighbourhood. And finally, just an hour away from the city is Gurnee Mills, a shopping mall with a wide mix of stores.

Unique to Chicago

If you visit Chicago in the winter months, put ice skating on The Ribbon on your list of things to do. Located in Maggie Daley Park in the heart of downtown Chicago, and with the city's skyline as a backdrop, The Ribbon is an outdoor ice track which meanders through a rolling landscape to provide an ice skating experience like no other. Skates are available to rent, and the Ribbon is usually open until late March. The Chicago Polar Plunge is another, if only as a spectator! Held at the beginning of March at North Avenue Beach in Lincoln Park, it's a special event in support of the Special Olympics, where thousands of people brave freezing temperatures to charge into Lake Michigan's icy waters. Chicago is also a wonderful place to see a Broadway-like show, with world-class venues including the Steppenwolf Theatre and the Goodman Theatre.

Take a tour

Chicago's history is a big part of what makes it so unique, and taking a tour is a great way to learn about the city's past, from the famous buildings to notorious gangsters. At the time of writing, Chicago's Landmarks was a half-day narrated coach tour taking in many of the city's most important landmark buildings and sights, including a scenic drive along the lake through Grant Park, down Chicago's Magnificent Mile, and exploring the South Side, including President Obama's former home. If you prefer to go at your own pace, the Hop-On Hop-Off Bus or Trolley Tour is an easy and convenient way to see the highlights of the city. If you are visiting during the warmer months, a Segway tour is another option, operated with small groups of just eight people and one guide. Another interesting option is the Chicago Mob and Crime Tour, which visits sites associated with some of the city's most notorious gangsters of the 20th century, including Al Capone. And for much of the year, the Chicago Architecture River Cruise sails past the city's fine buildings.

Stay somewhere fabulous

For most visitors, a hotel in the city centre is recommended, so you'll have access to the best sightseeing, shopping, dining and architecture. The city centre encompasses the famous Magnificent Mile and areas of the waterfront, which are particularly popular in summer. And for first-timers there's plenty of choice, from brand-new hotels to classics which have undergone dramatic renovations. Among the luxury hotels is The Langham, which has a lovely riverfront location as well as being close to the Magnificent Mile, Millennium Park and Navy Pier. The Hyatt Chicago Magnificent Mile (now Hyatt Centric Chicago Magnificent Mile) has also had a recent renovation, while the Radisson Blu Aqua Hotel has beautiful views over Lake Michigan and Millennium Park. For something a bit more stylish and unusual, the Acme Hotel Company (now ACME Hotel Chicago, Outset Collection by Hilton) is a hipster hotel located in Chicago's River North neighbourhood, which at the time had a focus on tech, including keyless room entry via an app, Amazon Echos in every guest room and ESP guitars in every suite.

Also one to consider at the time was Virgin Hotels; located in a stately old bank building, it had a cherry-red colour scheme, while being clubby and retreat-like at the same time. Virgin sold the hotel in 2025, and the building is being converted to Sports Illustrated Resorts Chicago.

And the contemporary-chic Viceroy is a designer's delight, with a retro Chicago façade and mid-century furnishings; a highlight at the time was quotes from Marcel Proust reproduced on the lobby wall.

Chicago's cuisine

Chicago used to have a bit of a reputation as a meat-and-potatoes kind of town, but that's no longer true. Restaurants in the Windy City today have a level of sophistication that rivals any food scene in the USA; although you can still get great steaks and hot dogs, as well as deep-dish pizza, the city has Michelin-starred dining experiences and some amazing cocktail bars. There are hundreds to choose from, and all types of cuisine on offer, but just a few to put on your list include Gibsons Bar & Steakhouse, located on North Rush Street. A Chicago icon since it opened its doors in 1989, it's famous for prime Angus beef, fresh fish and classic cocktails. There's also the curiously named Girl and the Goat, located on West Randolph Street, a decade-old hot spot where chef Stephanie Izard serves up innovative small plates from a dramatic open kitchen. Located in Chicago's historic Fulton Market District, Aba is a Mediterranean restaurant with a lovely rooftop patio, offering a lighter style of cooking with influences from around the Mediterranean, including Israel, Lebanon, Turkey and Greece. Meanwhile Galit is a Middle Eastern venue in Lincoln Park, with a menu focusing on a seasonal approach to dishes of the Middle East and Israel's immigrant cuisines. And finally, Chicago may be famous for its pizza, but a visit to Coda di Volpe, located in the Lakeview area, is essential, especially for fans of classic southern Italian cuisine including pasta, pizza, steak and seafood.

A pick of Chicago's best watering holes

Along with restaurants, hotels, sights… well, pretty much everything, Chicago has more than its fair share of amazing places to have a cold beer or a cocktail. A top pick is the rooftop bar at the Peninsula Hotel, Z Bar, which is arguably one of the best in the city. Located on the sixth floor, the bar opened in 2018 with a different perspective of the Mag Mile, fancy cocktail carts, and decadent drinks with ingredients like 24-karat edible gold flakes. Meanwhile Vol. 39, at the Kimpton Gray Hotel, is inspired by 1940s lounges, with book-lined walls and tufted-leather sofas. Also at the hotel is Boleo, located on the roof, with a Peruvian vibe and old-fashioneds as a focus. Ada Street is a go-to spot in Chicago for a romantic night out, located just north-west of Goose Island. Here the cocktails are inventive, with a rotating menu. Celeste is a River North venue reminiscent of an English garden, boasting a retractable roof which makes for year-round seasonal cocktails. And finally, Cindy's offers cocktails along with some of Chicago's most spectacular views across Millennium Park, the Art Institute and Lake Michigan.

If Chicago's architecture, neighbourhoods and food have you planning a longer stay, Pack Ya Bags puts together guided tours and ground itineraries in Chicago and across the USA for Australian and New Zealand visitors. Get in touch at info@packyabags.com

Editor's note. This article brings together UTM's original Exploring the Windy City: The Best of Chicago feature, first published in two parts, into a single piece. Consolidated and fact-checked on 22 September 2026.