Game-changing architecture, cutting-edge museums, world-class shopping, thriving culinary culture, major league sports and a buzzing music movement make Chicago one of the most-loved cities in the U.S.A. The city’s vibrant cultural scene, with its renowned arts, music, and entertainment offerings, draws visitors from around the world.
19th-century French stage actress Sarah Bernhardt dubbed Chicago as “the pulse of America” and the label still fits and the label still resonates today.
Chicago rapidly evolved from a small riverside trading post to a booming multicultural megacity, Chicago has managed to achieve a fine balance of tradition and creativity that has stood the test of time. As one of America's quintessential cities, Chicago’s history and cultural significance are woven into its fabric, making it a must-visit destination. The ‘Second City’ of the U.S. is a remarkable success story of man-made feats that included building a canal and sewer system, raising city streets, and even reversing a river. Ironically, it was a massive fire in 1871 that destroyed most of the city centre and gave birth to one of America’s most gasp-worthy skylines. With over 2.7 million people, the third largest city in America and the largest city in the Midwest is a preferred starting point for two of the country’s most soul-stirring road trips, the Great Lakes and a preferred starting point for the iconic Route 66 road trip and journeys around the Great Lakes region. It is widely believed that Chicago earned its nickname ‘the Windy City’ in the late 19th century. The editor of a major New York newspaper accused politicians in Chicago of spouting hot air - wind - while trying to attract the World’s Fair to the city. New York and Chicago were the two rivals to host the event … and in the end, Chicago won! The nickname stuck.
Let us first get our fill of “That Toddlin’ Town”.
Poised enviably on the banks of Lake Michigan, Chicago is the unequivocal cradle of modern architecture, with an urban skyline sculpted by the father of the skyscraper Louis Sullivan and Prairie School founder Frank Lloyd Wright. The soaring glass structure of the Willis Tower to the observation deck of 875 North Michigan Avenue (formerly the John Hancock Center) and the steely ribbons of Pritzker Pavilion to the skylit curvaceous lobby of the Rookery, dramatic artistry leaps out of architecture everywhere. Sparking curiosity even before even before you start digging deep to discover details like Art Deco elements and Tiffany design accents on the streets. Chicago is known for its stunning architecture, world-class museums, and a diverse culinary scene, making it a top choice for travelers seeking unique attractions.
Kickstart your exploration of the eminently walkable city with the Loop and the Gold Coast. Scour the 1.25 mile-long pedestrian stretch of the Chicago Riverwalk for waterfront eateries and eye-popping museums. From a refreshing boat cruise to a stint of active kayaking or even fishing, there are enough options for the outdoor enthusiasts. Bookmark the gargantuan video projection art installation, Art on the MART. Unwinding at the iconic 319-acre Millennium Park comes as a built-in. With time on your side, take more comfort from the fact that over 40 kilometres of lakefront, nearly 600 parks, beaches and bike trails await beyond the grid of busy streets. The Spring and autumn are generally considered pleasant times to visit Chicago are from April to May and September to October, when the weather is pleasant and a variety of festivals and events fill the city, making it an ideal time to plan your trip.
A lively big-city vibe meets warm Midwestern soul against a colourful kaleidoscope of 77 diverse neighbourhoods. One of the most charming areas to explore is Old Town Triangle in the Lincoln Park neighbourhood, which is dotted with buildings pre-dating the Great Chicago Fire of 1871. Stroll in the Hyde Park neighbourhood to find the University of Chicago campus, the Frederick C. Robie House, Hyde Park Art Center, and the 57th St Beach. Dip into the colourful canvas of street murals at the Hispanic neighbourhood of Pilsen. Study the row houses and restored company buildings at one of the earliest planned industrial communities in the U.S. built for employees of the Pullman Palace Car Company. First-time visitors should plan to explore Chicago’s diverse neighborhoods and attractions, each offering unique cultural, culinary, and sightseeing experiences.
Chicago after sundown is a city of glitter and verve. Aptly tagged by ‘The Guardian’ as “often regarded as one of America’s leading theatre cities”, the city has over 250 theatre companies. Award-winning stages, casual storefront shows and the latest Broadway hits, there’s a seat for everyone. The city’s live music is legendary, with countless jazz and blues clubs and rock bands, but there are plentiful choices for fans of comedy clubs and speakeasies too. Chicago’s music festivals, such as the Chicago Blues Festival in June and Lollapalooza in August, are major events that showcase the city’s rich musical heritage and are highlights of its cultural scene.
Professional baseball, basketball, football, hockey, and soccer teams make the city a sports buff’s dream destination. Chicago Bears, Cubs or White Sox, Bulls and Blackhawks, this is where all the high-pitched action is. Befriend the deep dish pizza – the best being Lou Malnati’s - and the Chicago dog, and you’ll feel completely at home.
Shopping
Indulge in shopping at The Magnificent Mile, the premier commercial strip that stretches between Lake Shore Drive and the Chicago River. Shopaholics can spend hours in anchor department stores like Bloomingdale’s, Nordstrom, Neiman Marcus, Saks Fifth Avenue and Macy’s or splurge at luxury boutiques like Burberry, Tiffany & Co. Bulgari, Cartier, David Yurman and Giorgio Armani. The eclectic collection of buildings here will thrill architecture fans. one of the few surviving structures from the Great Chicago Fire, Wrigley Building (former headquarters of the famous chewing gum company) and Tribune Tower (home of Chicago Tribune daily newspaper) are only some historic gems here.
If couture shopping is your poison, head to the tree-lined Oak Street in the historic and affluent Gold Coast. Notch up the day of exclusive glamour and cosy informality with a classic Chicago steakhouse experience.
Chicago’s State Street is filled with modern shopping centres, historic department stores and speciality stores. Millennium Park, the Riverwalk, Theatre District, and more classic Chicago sights are just a stone’s throw away.
Your search for vintage treasures, artisan goods and quirky shops ends at Lincoln Park, Wicker Park and Bucktown. To truly immerse yourself in Chicago’s local culture, shop in these neighborhoods to discover unique experiences and hidden gems that reflect the city’s authentic character.
Museums & the arts
Seek out the most monumental public sculpture, Cloud Gate (The Bean), in downtown Millennium Park. Designed by Indian-born British artist Anish Kapoor, its sleek, reflective surface is a favourite photo-stop for every first-time visitor.
Chicago is home to world-class museums, many of which are located on the scenic museum campus—a must-visit destination that brings together the Field Museum, Shedd Aquarium, and Adler Planetarium for a comprehensive cultural experience.
The Field Museum is a treasure trove of exhibits on everything from ancient cultures to scientific discoveries, from Egyptian tombs to the most mammoth creature on earth. There is something to interest every museum enthusiast.
The Art Institute is a mecca for every art lover, renowned for its Impressionist collection and considered one of the world's top museums. Study impressionist works by Monet, Renoir, and Van Gogh. Ogle at masterpieces by Chagall, Dalí, Matisse, Picasso, and Pollock. Add a trip to The Museum of Contemporary Art for 2500 artworks across genres like surrealism, minimalism and conceptual photography.
The Chicago Cultural Center in the downtown Loop neighbourhood is a definitive institution. Go to see the world’s largest Tiffany stained-glass dome, mother of pearl mosaics and a Carrara marble lobby. Catch a free acoustic experience or pick up an artisanal product.
Step into the world of more than 32,000 aquatic animals at the Shedd Aquarium. Don’t miss the beluga whales and Pacific white-sided dolphins housed in the Abbott Oceanarium.
Sports
Chicago Cubs is one of the city’s two Major League Baseball franchises. Sports buffs can book tickets to the game at the second oldest baseball park in America, Wrigley Field. Consider a private tour of the ivy-covered 1920s stadium with your own personal tour guide. A pre-game drink at the sports bars lining Clark, Addison, and Sheffield avenues in Wrigleyville is on the cards.
Soldier Field, a historic and iconic sports arena, is the home stadium for the Chicago Bears football team and hosts major sporting events and concerts, making it a must-see for fans of American football and sports history.
United Center is home to the Chicago Bulls of the National Basketball Association and the Chicago Blackhawks of the National Hockey League. Pose with the statues of legends like Bobby Hull, Stan Mikita and former Bulls star Michael Jordan. Celebrate your love for sports and bond with fellow fans at the Billy Goat Tavern, Goose Island Taproom or bars of Randolph Street.
Golfing fantasies come to life at one of the in the wider Chicago area. Take your pick from historic Jackson Park Golf Course, award-winning Harborside International Golf Center, or lakefront Sydney R. Marovitz Golf Course. Nearby, Lemont is home to golf courses such as Cog Hill Golf and Country Club, which have hosted professional tournaments.
Restaurants and bars
Alinea Restaurant is known for modernist cuisine created with the world’s best luxury ingredients. The innovative signature dish is an edible, helium-filled, floating balloon designed by former executive chef Mike Bagale. The three star Michelin restaurant promises exclusivity with a glassed-in kitchen table for four to six diners and a bespoke menu with over 22 courses.
Experiment with creative New American cuisine at the 80-seat industrial styled S.K.Y. Relish contemporary cuisine and eclectic beverages in a 2-star Michelin establishment that celebrates the arts culture of Pilsen. The seared Scottish salmon with cauliflower caponata and white shrimp ceviche comes highly recommended.
The 14-course menu at Oriole is indulgent and satisfying with contemporary, global flavours. Settle into casual chic of exposed brick walls and massive wooden beams in the 2-star Michelin restaurant. Specials include Raw oysters with some pork consommé to capellini with a yeasty butter sauce topped with truffle shaved table-side.
Moody Tongue, awarded 2 Michelin stars, stands out with a seasonal, creative menu and house-crafted brews. The poached Maine lobster in spiced tomato water, accompanied by a sour watermelon saison, is one of the must-try dishes. So is the Seared Hudson Valley foie gras with burnt peach dashi and pistachio streusel.
Chicago’s food scene is as diverse as its neighborhoods, offering everything from classic American fare to international cuisines that reflect the city’s rich immigrant history. Don’t miss iconic local dishes like deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs. The Italian beef sandwich, a beloved local favorite, features seasoned roast beef soaked in meat drippings and topped with spicy giardiniera or sweet Italian peppers—try one at Portillo’s for an authentic experience. The Chicago-style hot dog is an all-beef frankfurter served on a poppy seed bun, loaded with yellow mustard, neon green relish, chopped onions, tomato wedges, a pickle spear, sport peppers, and a dash of celery salt—but never ketchup. From fine dining to classic street food, Chicago’s culinary landscape is a true reflection of its vibrant, multicultural heritage.
Exclusive experience
Notch up the sightseeing with a helicopter ride over The Chi-Town. Glide across the scenic waterfront, spot the most significant landmarks of the skyscraper-studded cityscape. Expect a state-of-the-art aircraft and experienced pilots who will share lore and legends of the city. Exhilaration guaranteed.
Must-buy souvenir
Chicago has been voted the Best Sports City three times and is home to multiple professional sports teams. Fans of sports and particularly, baseball cannot resist buying a Bulls or Bears jersey or a baseball cap.
Side trip
Venture out to Oak Park, Illinois, home of visionary architect Frank Lloyd Wright, who pioneered the Prairie style of architecture in the early twentieth century. The residential suburb of Chicago is famous for the most extensive collection of Wright-designed structures. Expect to see two UNESCO World Heritage Sites, Unity Temple and Robie House. The Wright Plus Housewalk, run by the Frank Lloyd Wright Trust, offers tours of the privately-owned Frank Lloyd Wright-designed homes in the area.
Nightlife / Hidden gem
Reserve an evening for one of the oldest nightclubs in the city and a favourite haunt of Al Capone himself. Since 1907, the Green Mill has pulled guests with its vintage charm, low-lighting, red booths, whiskey barrel tables. Swing through the night with live music, nightly jazz performances, and late-night jam sessions by local artists.
Hotels
Chicago boasts a plethora of amazing hotel properties known for their wonderful guest experiences, exceptional quality of service, and overall satisfaction. From the magnificent Peninsula, Chicago to the excellent boutique Talbott (part of Hyatt), the city offers something for everyone. The Gold Coast and the Magnificent Mile – where there are seventy hotels – are the most popular locations to stay.
Read our First-Class.com guide to The Best Luxury Hotels in Chicago.
Getting there
The city has two international airports – O'Hare International Airport and Chicago Midway International – that serve nearly 300 destinations. O'Hare International Airport is a hub for American Airlines and United, and offers a convenient connection to downtown Chicago via the CTA Blue Line of the L train system, making it easy for travelers to reach the city center. Midway is a focus for Southwest. Both are filled with lounges, shopping and dining facilities.
Getting around
Public transportation is essential for navigating Chicago efficiently, with the city offering an extensive public transit system and being highly walkable, especially in downtown areas. Chicago's public transportation system, operated by the Chicago Transit Authority (CTA), includes the 'L' train and an extensive bus network, making it easy to reach various neighborhoods. The 'L' train serves almost 150 stations and connects diverse areas, while buses extend the network to locations not covered by the train. Metered taxis, as well as Uber and Lyft rideshare services, are also readily available, providing convenient alternatives for getting around the city.
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