Search and Compare Chicago Flights

Direct flights to Chicago fly into Chicago O’Hare International Airport, about 17 miles northwest of the Chicago Loop and Chicago Midway Airport, on the southwest side of the Loop.

Chicago’s northern location means that it experiences four distinct seasons: a hot summer, cold winter, and mild spring and autumn. Summer brings with it bright sunshine and thousands of tourists; spring and autumn are pleasantly warm and, if you plan your trip to Chicago outside of the school holidays, you should be able to take advantage of festivals, warm temperatures, and fewer tourists. Spring and autumn have the benefit of being slightly cheaper than the summer, but if you want really cheap flights to Chicago, consider braving the freezing temperatures in winter, where you will find Chicago crisp and sparkling in its festive finery. Chicago is notoriously cold in the winter, but with the right outerwear, you can experience the stunning city under a cleansing blanket of snow.

Sport is such an integral part of Chicago’s culture that most inhabitants possess rigid opinions about their teams! Chicago is home to prominent teams from four of America’s major sports: American football, basketball, hockey and baseball. Most people from Chicago will be fanatical about at least one sport; if you can’t go to a live game, soak up the atmosphere in a bar while avid fans cheer on their team. For a whistle-stop tour of Chicago’s illustrious sporting history, we suggest a trip to the Sports Museum

Eateries, shopping and fantastic architecture; a day downtown will leave you exhilarated, and maybe a little exhausted. Aside from shopping along Magnificent Mile, downtown Chicago is home to incredible architecture which pays tribute to modern and classic forms from across the globe. In 1922, to celebrate 75 years of publications, the Tribune’s co-publishers announced a competition. The brief was to design “the most beautiful building in the world”. And so, the building of the Tribune Tower commenced. It was completed in 1925: a spectacular, 141-metre-tall gothic skyscraper, built upon bricks from some of the most famous buildings in the world. There is no doubt that beauty is subjective, but a building which pays homage to centuries of classic architecture and incorporates bricks from 120 critical locations, such as Angkor Wat, the Great Wall of China, the Pyramids and the Parthenon, is pretty hard to beat. Formerly the Sears Tower, the Willis Tower may have lost top spot as the world’s tallest building, but it is still incredible to behold. If you are feeling brave, you can travel to the viewing gallery on the 103rd floor, where you can take in the incredible view of Chicago, spread out more than a kilometre below. If you prefer to keep your feet slightly closer to the ground, head to the Navy Pier, where there are plenty of family-friendly rides and museums, as well as fabulous views. If you plan your trip to Chicago in the winter, you will witness the unbelievable site of Lake Michigan frozen solid. If you visit during the warmer months, consider taking a bike ride along the Lake Shore Trail.

If downtown hasn’t sated your appetite for architecture, take a trip to Oak Park. Discover the lives and times of Frank Lloyd Wright or Ernest Hemingway on organised tours; visit Wright’s first studio, or wander around Ernest Hemingway’s childhood home. The Art Institute of Chicago is the largest art museum in Midwest America, and one of the best in America. As you enter via magnificent stone steps, flanked by lions, you will discover a dazzling array of more than 260,000 pieces from around the world.

Chicago is all about red meat, comfort food, and plenty of carbs. Like many large, vibrant cities, clusters of restaurants from different cultures are springing up, meaning that whether you fancy Chinese, Italian, Vietnamese or good old American, it isn’t too hard to find what you want. It is not possible to go far in Chicago without stumbling across an Italian Restaurant. And, as Chicago is home to the original deep pan pizza, it would be rude not to sample a little Italian fare, Chicago style. Finding a restaurant that makes authentic dishes, just like Mama used to make can be a challenge, so head to Taylor Street, dubbed the Heart of Italy, where you will find a host of traditional Italian restaurants. Spend an afternoon at Fulton Market, where you can treat yourself to a famous Mr. G sandwich (go later in the afternoon to avoid queuing); sample exquisite cured meats, or a slice of delectable deep-pan pizza. Or head to Spanish Square where you can enjoy tapas and Spanish wines the likes of which you are unlikely to discover anywhere else outside of Spain. If you are a lover of beer, spend some time sampling the many home-grown brands that Chicago has got to offer. There are a range of beer tours that take you through the city’s exciting history of brewing; the best bit is, you get to sample some along the way. Chicago is a city that celebrates its past by creating a vibrant future. Everything feels solid, dependable and possesses a quiet, dignified confidence that makes visitors to Chicago feel instantly at home. If you want to find your little piece of the Windy City, let Travangelo help you to find cheap flights to Chicago.