City Guide to Chicago

Chicago – The Windy City

20. Aug 2021
by Punita Malhotra

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.

19th-century French stage actress Sarah Bernhardt dubbed Chicago as "the pulse of America" and the label still fits like a well-worn glove.

Rapidly evolved from a small riverside trading post to a booming multicultural mega city, Chicago has managed to achieve a fine balance of tradition and creativity that has stood the test of time. The second city of U.S.A is a remarkable success story of manmade 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 gape-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 the Route 66. Myth has it that Chicago earned its nickname the Windy City in 1890. 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 teetering glass box of the Willis Tower to the observation deck of the deceptively simplistic John Hancock Tower and the steely ribbons of Pritzker Pavilion to the skylit curvaceous lobby of the Rookery, dramatic artistry leaps out of architecture everywhere. Pumping up your exploratory instincts even before you start digging deep to discover details like Art Deco elements and Tiffany design accents on the streets.

The Willis Tower (formerly knows as the Sears Tower)

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 outdoorsy. Bookmark the gargantuan video projection art installation, Art on theMART. 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 39 kilometres of lakefront, 552 parks, beaches and bike trails await beyond the grid of busy streets.

The Chicago River

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 Pullman, the first industrial planned community in the U.S.A, built for employees of the Pullman Palace Car Company.

The University of Chicago - one of the best in the USA

Chicago after sundown is a city of glitter and verve. Aptly tagged by 'The Guardian' as "the theatre capital of America", the city has over 250 theatre companies. Award-winning stages, casual storefront shows and the latest Broadway hits, there's a seat for every king seat. 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 Theatre

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 Malnati’s - and the Chicago dog, and you’ll feel completely at home.

The Bears


Burn a hole in your wallet 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. Historic Water Tower, the oldest standing structure on Michigan Avenue, 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.

A floral Magnificent Mile

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.

The affluent Oak Street

Chicago's State Street is stuffed with modern malls, historic department stores and speciality stores. Millennium Park, the Riverwalk, Theatre District, and more classic Chicago sights are just a stone's throw away.

Street life, Chicago

Your search for vintage treasures, artisan goods and quirky shops ends at Lincoln Park, Wicker Park and Bucktown.

Crown Point

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.

The Bean

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 nerd.

The Field Museum

The Art Institute is a mecca for every art lover. 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 Art Institute of Chicago

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.

The Chicago Cultural Center

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.

Shedd Aquarium


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.

Wrigley Field

United Centre 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 Mitka 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.

The Chicago Bulls

Golfing fantasies come to life at one of the 200 golf courses in the city. 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.

Sydney R. Marovitz golf course

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.

Alinea - three Michelin star masterchef - Grant Achatz

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.


Acadia whips up New American dishes inspired by coastal Maine. Opt for the 10-course tasting menu to pamper your palate with unique creations like A5 Miyazaki with charred pineapple Yuzu Kosho and uni mayonnaise and strawberry mousse with duck yolk crema.


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.

Moody Tongue 

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.

Chicago as the sun sets

Must-buy souvenir

Chicago has been voted the Best Sports City three times and is home to 5 professional teams. Fans of sports and particularly, baseball cannot resist buying a Bulls or Bears jersey or a baseball cap.

Bulls legend Zach LaVine

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 Home. 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.

Frank Lloyd Wright  - Oak Park

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. 

Green Mill cocktail lounge


Chicago boasts a plethora of amazing hotel properties. 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 guide to The Best Luxury Hotels in Chicago

Peninsula, Chicago

Getting there

The city has two international airports - Chicago O'Hare International and Chicago Midway International – that serve nearly 300 destinations. O’Hare is a hub for American Airlines and United …while Midway is a focus for Southwest. Both are filled with lounges, shopping and dining facilities.


Getting around 

Chicago has a well-connected public transit system of trains and buses. The train system, nicknamed the "El", runs above ground across much of the city and is a convenient way to commute from O'Hare and Midway airports to downtown Chicago. Metered taxis as well as Uber, Lyft cabs are readily available.

Overground on the L train service searches hundreds of travel sites at once to help you find the best premium travel offers for both flights to and from the city and accommodation in Chicago.

More from
City Guide to Cape Town
Cape Town And Her Iconic Table Mountain

Table Mountain looms above the city and Capetonians speak of its protective powers. Edged by impressive cliffs and flanked by Devil’s Peak... Finest Selection
The Best Dive Sites in Maldives

The Maldives is renowned for its stunning beaches, azure – calm seas, wonderful – temperate climate, stunning hotels, and incredible flora...

Special Offers
Business Class from Europe to Cancún and Punta Cana from €999 / £1,115

TAP Air Portugal is offering special Business Class fares to Caribbean destinations Cancún, Mexico and Punta Cana, Dominican Republic from...