Flights to Chicago

Perched on the shores of Lake Michigan, where the lake winds have helped coin the term Windy City, Chicago affords visitors and residents truly spectacular views. Its vantage point has even landed it some memorable roles over the years. Anyone who has seen Ferris Bueller's Day Off has witnessed a love letter to Chicago with cameos of The Art Institute of Chicago, Wrigley Field, the Willis Tower and more.

It's no secret that Chicago, the third-most-populous city in the country, is also one of the most diverse cities in America. But what's especially interesting is that many neighborhoods are true reflections of the immigrants who established them. Vietnamese, Thai, Laotian, Mexican, Puerto Rican, Irish, Polish, Korean and other cultures add their own nuances to the city's unique cultural flavor.

Chicago has also morphed into the literary landscape for books like The Jungle, The House on Mango Street and The Lazarus Project. Not to mention its prime real estate on Broadway as the subject of one of the best-known musicals of all time. No matter your taste in food, culture, sports or fun, Chicagoland has something to offer everyone.

When flying into Chicago, you have two destination choices. The city has two international airports within its limits: Chicago O’Hare and Chicago Midway. The former is considered the primary and the latter the city’s secondary.

In the past, O’Hare has ranked as the busiest airport in the world by numbers of takeoffs and passengers. It has no shortage of restaurants and cafes, bars and grab-and-go options. It also has retail shopping, duty-free items and even spa services.

At Midway you’ll find the same variety of sit-down and fast-food options. A number of its retail stores have a Chicago focus so you can also pick up last-minute souvenirs on your way out of town. And if you’d rather unwind, there’s even a free yoga room reserved for yoga practice and meditation.

  • Both O’Hare and Midway airports are located within the city of Chicago. Midway sits on the southwest side of Chicago, eight miles from the Loop (downtown Chicago’s central business district). O’Hare is located on the far northwest side of the city, about 17 miles from the Loop.
  • It’s easy to get into the city from both airports with service from Chicago Transit Authority’s L Trains. At O’Hare, the Blue Line station is on the lower level of Terminal 2. At Midway, find the Orange Line station just east of the terminal building at the Midway Transportation Center.
  • O’Hare has access to Metra, Chicago’s commuter rail system. Just board the airport shuttle bus for a ride to the O’Hare Transfer Station.
  • You’ll also find taxi, limo service and rental cars at both locations.


One of the most celebrated parts of Chicago's culture is the jazz. Sink into one of the local haunts like Andy's Jazz Club or Kingston Mines to take in the blasting sounds of trumpets roaring or the salty quakes of the saxophone. If you want to hear it all in one place, visit the city during The Chicago Jazz Festival, which takes place over Labor Day weekend. If you're an alternative music lover, you're probably already planning a trip to the Pitchfork Music Festival in July or Lollapalooza in August.


Chicago's a museum city. Visit the Shedd Aquarium to experience one of the most well-tended oceanic museums in the country. An Oceanarium and multiple Wild Reef exhibits are on hand for an underwater experience that's as educational as it is entertaining.

Tackle as many of the Art Institute of Chicago's four buildings as you can, then prepare for your jaw to drop ¾ and stay dropped ¾ at The Museum of Science and Industry. Highlights include a simulated coal mine tour and giant Fairy Castle complete with tiny chandeliers made out of real diamonds.


It won't take you long to see that Chicago is a foodie town. Aside from mastering deep-dish pizza at places like Pizzeria UNO or Lou Malnati's, there isn’t a cuisine in Chicago that's not represented…and represented well. Its Chinatown is legit. The Indian food on Devon Avenue and the Persian food on Kedzie Avenue are worshipped. There's a Little Italy, a Greektown, a Polish Village and the list goes on and on.

And a good brew is never far out of hand, either. Behind San Francisco, Chicago has the second highest rate of bars per capita.


Chicago has long been a city associated with architectural experimentation and innovation. From the soaring Willis Tower with its 103rd floor glass-bottomed balcony to the 1920s-era Wrigley Building skyscraper and the iconic Chicago Theatre with its six-foot triumphal arch, the city is studded with architectural gems. No matter your favored mode of transportation, be it by boat, bike, trolley, segway or foot, there’s an architectural tour to suit you. 

Chicago's hotel scene is hot. In fact, the city ranks second only to New York City in its number of guest rooms, so you should have no trouble finding lodging that fits your mood, interests or budget.

Want to stay where British royalty, U.S. presidents and king of cool James Dean have all laid their heads? Then the famed Drake Hotel is your place. Located on the lake side of Michigan Avenue, the hotel’s north-facing rooms feature lake views, which are definitely worth springing for. Though the common areas of the 1920s-era hotel are gilded and chandelier-strewn, the guest rooms are more laidback. And don’t forget afternoon tea is held daily in the Palm Court.

If you’re going for a more boutique vibe, the Guesthouse Hotel north of downtown in the Uptown neighborhood is a splurgy choice. The 25 former condominiums have been converted into stylish suites complete with full kitchens, private balconies and even washer-dryers.

And for a stay that promises to channel the city’s urban-hip side, try the W Chicago City Center. Located in the Loop just blocks from the Willis Tower, Millennium Park and Magnificent Mile shopping, the hotel features sleek contemporary guest rooms and suites.

Before planning a trip to Chicago, you’ll want to consider what kind of weather you’re up for. The city sees hot and humid summers and infamously cold and snowy winters with little sun. In July, the average daily temperature is around 76°F, but it’s not uncommon for the mercury to rise to 90°F or higher. In the winter, the normal January high (yes, high) is just below freezing. Spring and autumn are generally pleasant times to visit, with mild temperatures and low humidity.

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