Chicago Travel Guide: Things to Do, Best Time to Visit & Itinerary

Chicago is a city that commands attention, rising from the shores of Lake Michigan like a steel and glass fortress. Known as the “City of Big Shoulders,” it possesses a grit and determination that is palpable in its bustling streets, yet it balances this industrial history with stunning public art and acres of green space. Whether you are gazing up at the skyscrapers that invented the modern skyline or looking down at the icy blue waters of the lake, the energy here is undeniable.

The locals are as much a part of the attraction as the buildings; unpretentious, friendly, and fiercely proud of their city. From the polished avenues of the Gold Coast to the hipster enclaves of Wicker Park, Chicago offers a patchwork of neighborhoods, each with its own distinct flavor, cuisine, and rhythm. It is a city that invites you to walk its riverbanks, eat until you can’t move, and soak in the history of American architecture.

The City That Changed Architecture

Following the Great Chicago Fire of 1871, which destroyed over three square miles of the city, Chicago didn’t just rebuild; it reinvented. Architects flocked here to experiment with new materials like steel, giving birth to the world’s first skyscrapers. This tragic history paved the way for a skyline that is now considered a living museum of architectural innovation.

Today, you can trace the evolution of design simply by walking down the street. You will see the heavy masonry of the early 20th century standing shoulder-to-shoulder with the sleek, mid-century modernism of Mies van der Rohe and the contemporary spirals of Jeanne Gang’s St. Regis. This juxtaposition of the old and the new is what gives Chicago its unique visual texture and makes a simple walk around the Loop an awe-inspiring activity.

The Icons You’ll Want to See

Willis Tower (Skydeck) - Standing 1,451 feet tall, this building (formerly Sears Tower) offers views spanning four states on clear days. General admission is $35, and it is located 0.8 miles west of the lakefront.

The Field Museum - A massive natural history museum on the lakefront campus, famous for ‘Sue’ the T. Rex and ancient Egyptian tombs. Tickets are roughly $30, located 2 miles south of the Loop.

Shedd Aquarium - An indoor public aquarium housing 32,000 animals, located right on Lake Michigan next to the Field Museum. Admission is approximately $40.

360 Chicago - Located on the 94th floor of the former John Hancock Center, offering ‘The Tilt’ thrill ride. It is located on the Magnificent Mile, with tickets starting at $30.

Planning Your Visit

Chicago is served by two major airports: O’Hare (ORD) and Midway (MDW). O’Hare is massive and international, connected to the city by the Blue Line ‘L’ train ($5 fare), which takes about 45 minutes to reach downtown. Midway is smaller, closer to downtown, and served by the Orange Line ($2.50 fare), taking about 25 minutes. Do not rent a car if you plan to stay in the city; parking is notoriously expensive (often $50+ per night), and the public transit system is excellent.

Getting around is best done via the CTA ‘L’ trains and buses. Purchase a Ventra card at any station for seamless travel. In the warmer months, the Chicago water taxi is a scenic and practical way to move between the Loop, Chinatown, and Goose Island. Pack comfortable walking shoes, as the city is built on a grid that begs to be explored on foot.

Chicago is a destination that rewards the bold and the hungry. While the winters can be harsh, the warmth of the hospitality, and the calories in the deep-dish pizza, more than make up for it. Whether you come for the summer festivals or the winter lights, you will leave with a deep appreciation for this Midwestern giant.