A Traveling Insider’s Guide to Chicago
Allow us to help you navigate your Chicago vacation using this guide to the Windy City.
By Paul Oswell | August 13, 2021 (Updated: July 3, 2025)
Paul Oswell
Paul Oswell is a British award-winning journalist and published travel author based in New Orleans, Louisiana. His books include Bucket List North America and The Great American Road Trip, as well as New Orleans' Historic Hotels. He has also been an editor of and contributor to several guidebooks/editions published by Dorling Kindersley (owned by Penguin), including New Orleans, Florida, Orlando, Los Angeles, California, and The United States. His work has appeared in Conde Nast Traveler, Travel & Leisure (both of which he has written multiple online travel guides for) and The Guardian, as well as dozens of international newspaper and magazine titles, and inflight magazines for major airlines.
Chicago is a quintessential American city, a diverse concoction of urban grit and high finance, towering skyscrapers, vibrant immigrant communities, and thriving suburbs.
Defined by its proximity to Lake Michigan, Chicago’s early 20th-century reputation as a home to mob bosses and a Prohibition battleground has endowed the city with a unique edge. But Chicago has shed that persona over the last 100 years, and its expansion and growth have transformed it into a welcoming and multi-faceted destination.
Here’s our guide to enjoying this beautiful town.
Outdoor adventures
Park Place
The city’s 570 parks — yes, you read that right — help add natural beauty between the dense neighborhoods. Lincoln Park alone stretches for some 1,200 acres (485 hectares), and the lawns and festivals of Millennium Park and Grant Park welcome thousands of people every week.
Green Garden
Lake Michigan has shaped Chicago’s evolution and contributed to the city’s motto, urbs in horto — “City In a Garden” — also a reference to its extensive green spaces. Few large American cities enjoy close access to such huge swathes of shoreline, and the miles of lakeside parks and beaches offer acres of recreational space.
Shore Thing
The shores of freshwater Lake Michigan are home to some 24 beaches, with North Avenue Beach being by far the most popular. In the summer months, the volleyball games and DJs make it indistinguishable from its Californian cousins. For a more mellow, family experience, check out 57th Street Beach, or visit Montrose Beach for watersports.
Slice of life
Deep-dish pizza reigns supreme in Chicago, and locals have fierce loyalties as to where the best pizza can be found (check out Lou Malnati's, Giordano’s, Labriola’s, and Gino’s East, to name several of many).
Chicago also has its own barbecue, hot dogs, and sandwich styles. You won’t find better old-school steakhouses than those typified by Gene & Georgetti (established in 1941), but there are cutting-edge restaurants to explore as well. If you have a sweet tooth, brownies were invented here (at Palmer House, a Hilton Hotel, no less!), so plan to stop in for a visit.
Getting to and around Chicago
O’Hare International Airport
O’Hare International Airport is one of the busiest in the world and is a hub for hundreds of domestic and international flights. It is 20 miles (32 kms) or so northwest of downtown Chicago. The Chicago Transit Authority’s (CTA) Blue Line train connects O’Hare to downtown. Taxis and ride-hailing apps are both operational, and driving downtown takes around 40 minutes with minimal traffic, but double that during peak times.
Chicago Midway International Airport
Chicago Midway International Airport is the city’s second airport hub, serving mostly domestic flights. The CTA’s Orange Line train connects Midway to downtown. GO Airport Express offers a shuttle service from both airports, stopping at requested stops downtown.
The “L”
The CTA train network is known as the “L” (short for elevated train) and has eight lines, identifiable by color, that connect many parts of the city. Some lines run 24 hours per day. A regular fare is $2.50, but you can also buy Ventra transit cards for topping up or to use as day passes. A Ventra transit card can also be used for the CTA bus service, which covers the entire city.
Pedal power
Chicago is a great city to bike around, with more than 200 miles of bike lanes. Walking is also encouraged, particularly around downtown and Northside.
Unless you have further travels planned, it’s best to avoid the stress and expense of a car rental. Traveling between neighborhoods is easy by either taxi, public transportation, or ride-hailing services.
Things to do in Chicago
The city is rightly proud of its buildings, and we recommend taking an architectural tour to learn more about them; there are several options, including walking and from the water. The Willis Tower (formerly known as Sears Tower) was the tallest building in the Western Hemisphere for 40 years. The Rookery and The Reliance Building are a couple of the world’s oldest skyscrapers, and 875 North Michigan Avenue (previously called the John Hancock Center) and Marina City are awe-inspiring.
Chicago is home to the largest art museum in the Midwest, the Art Institute of Chicago. Its glorious beaux-arts exterior beckons visitors to explore its huge collection, some 260,000 pieces. The Field Museum offers an endlessly fascinating collection of cultural treasures from around the world, while the family-friendly Museum of Science and Industry was the first museum to have interactive exhibits, some dating back to the 1930s.
Chicago is also a city where musicians of all genres thrive, with more than 200 music venues and clubs alone. The jazz and blues scene is alive and well here, including legendary venues such as the Green Mill and Winter’s Jazz Club. For a change of pace, there’s the Lyric Opera of Chicago and the Chicago Symphony Orchestra.
Popular attractions
Museum Campus
Five of the city’s most popular attractions are contained on Museum Campus, which spans 57 acres (23 hectares) within Grant Park. The campus houses the Adler Planetarium, the Shedd Aquarium, the Field Museum, Soldier Field (home of the Chicago Bears football team) and the Lakeside Center of McCormick Place.
Public art
The city’s public art is among the best in the world, with the most prominent examples being the untitled Picasso sculpture at Daley Plaza, and the “Cloud Gate” (affectionately referred to as “The Bean”) — a huge, abstract shape that is covered in reflective stainless steel. The Chicago Riverwalk, located on the banks of the Chicago River, also offers artful displays, most notably the video art that happens during Art on theMART.
Wildlife
Proximity to nature means that wildlife is also an important part of city life here. The beautiful beaux-arts Shedd Aquarium has been welcoming visitors since 1929, and is home to 32,000 marine animals representing over 2,000 species. Lincoln Park Zoo dates back to 1868 when it opened with a pair of swans. It’s a free facility, with a bird house, a polar bear pool, and the exotic Regenstein African Journey exhibit, with rhinos, hippos, and giraffes.
Theater arts
Among the performing arts heavy hitters are the Goodman Theatre (founded in 1925) and the Chicago Shakespeare Theater, the cultural versatility of which stretches beyond the Bard’s works. Comedy fans will likely want to make a pilgrimage to The Second City to see the institution that birthed comedic legends.
More things to do
The city boasts a rich architectural heritage, museums, art, music, and must-try eateries. If you have some extra days, you’ll find charmingly characterful neighborhoods in Greek Town, Chinatown, Little Italy, and West Town.
Many modern cities have a redeveloped waterfront area that has been transformed into an entertainment, dining, and retail center, and Chicago’s is Navy Pier. Renovated for its 2016 centennial, Navy Pier now boasts fairground rides, interactive water features, the Chicago Children’s Museum, and the Centennial Wheel, a 200-foot-tall Ferris wheel that delivers sensational lake and city views.
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