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Chicago Flights & Travel Guide

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Why fly to Chicago?

Deep dish pizza and a night of blues welcomes you into Chicago. The city of course is a whole lot more than that but nothing is more welcoming than delicious food and music for the soul. Chicago is the state of Illinois' largest city and a major US economic hub.

The city located on the shores of Lake Michigan is one of the first homes of skyscrapers in North America. The Great Chicago Fire led to massive construction and the visionaries in the city didn't just rebuilt they reinvented to create an ultra-modern city.

Buildings like the Willis Tower and the Chicago Board of Trade are some of the tallest in the world. Chicago is also home to fantastic museums and galleries like the Art Institute of Chicago and the Museum of Contemporary Art. But the art in the city isn't confined to the walls of buildings, the city has a great public art scene.

Pieces like Calder's Flamingo and Cloud Gate dot the city and give Chicago a bit of a European feel in the heart of the US. A statue of Abraham Lincoln is particularly poignant and deserves a visit. The city is also home to numerous parks with Lincoln Park the largest, the green in the city is absolutely refreshing among the skyscrapers and the sheer quantities of parkland mean a dip into green is usually just a few feet away, something unusual in most urban areas.

Chicago is known for its distinct food flavors. Michelin doesn't need to star what comes out of Chicago kitchens as the satisfied and satiated patrons of Chicago cuisine tell the story themselves.

One, try deep dish pizza in Chicago - it will blow your mind. The pizza is oozing with melty cheese and lycopene-healthy tomato sauce. Add to it what you will, but it is the buttery, fluff-melt base that will have you dreaming of this long after you leave. After the pizza a proper Italian roast beef sandwich is in order. The tender slices are locked into a pillowy bun and topped with oh-so-sweet or oh-so-hot-hot peppers and then dunked into a delicious au jus. Take a moment.

Ok, next is a Chicago hot dog, and you don't have to go to Dodgers Stadium to get one. Take a beefy frankfurter, load it with tangy mustard and top it with tomato, onions, relish, hot peppers. Sublimely done.

Additionally, you can venture into the city's fine restaurants, many of which are located near the water and enjoy a night of fine food followed by dancing near the harbourfront. Nightlife is eclectic and can arrange from a night of classy jazz to gyrating hip hop.

Chicago has it all, it has managed to couple economic superiority with a green thumbprint and sprinkle that with awesome art and food. All of that creates a city worth visiting simply for the appreciation of what is super in the world.

Chicago Weather

Chicago doesn't mess around when it comes to its weather conditions. When it's hot, it's sizzling and when it's cold even your nose hair freeze. During the summer, the temperatures are between the high 20s and the low 30s and that is also when the city experiences most of its rainfall. The winters are cold and temperatures drop below 0, at time to -10. Snowfall is sporadic through the winter period.

When to fly to Chicago

Peak season

Summer is a busy time of year for everything in Chicago. The weather is hot so tourists flood the city to take in the sights. Summer is also festival season, which means folks are flying in to attend or perform. Either way, flight prices are high in the summer months.

Off season

Visitors to the city decline when the cold weather hits. January through until March is the best time to score flight deals for a trip to Chicago. October and November are also not quite as busy as the summer and the weather is better than the January to March period, so this would be an ideal time to book.

Getting into Chicago

Your gateway into the city opens up at O'Hare International Airport. There are several ways to get into the city once you land. Your options include public bus or the L-train. There are also private shuttle companies operating from the airport that travel certain routes throughout the city. Additionally taxi service is also available.

Getting around Chicago

Chicago is a very easy city to travel. The interconnected public transportation system is made up of buses, subway as well as the

elevated train. The Metra rail system will connects the downtown to the suburbs. You can also rent a bike or grab a taxi if you are feeling active or lazy respectively.

Insider Guide

  • Head to Navy Pier for a fantastic afternoon and perhaps evening too. The boardwalk in the city is a popular area for families, cyclists and bladers. Additional the pier has some great little shops that carry everything Chicago-esque as well as wonderful restaurants ranging from authentically Italian to a good old-fashioned tavern.
  • The pier is also home to the the Shakespeare Theater, and if you can snag tickets you are really in for some great theatre.
  • Spend a day at the lake. Chicago's lakefront is a popular recreation area and in the summer it turns into a hub of activity with free concerts offered through the warm month as well as various festivals taking place.
  • Even if you're not a baseball fan, you must visit Wrigley Field. It is only second to Fenway Park in Boston in historic value.
  • Compare flights to Chicago from Australia on

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O'Hare International Airport More information at

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Cheap Flights to Chicago (CHI)

Historical prices for Chicago flights.

Departure Airline Prices
Bozeman Frontier $322
Laredo Continental $273
San Diego Alaska Airlines $215
Kansas City American Airlines $119
Toronto Air Canada $214
Madison American Airlines $212
Phoenix American Airlines $222
Raleigh Durham American Airlines $160
Newark American Airlines $178
Cedar Rapids American Airlines $251
Burbank American Airlines $223
Hartford Springfield American Airlines $207
Baltimore American Airlines $177
Philadelphia American Airlines $211
San Francisco Alaska Airlines $246
Fresno American Airlines $285
Eau Claire Continental $228
Frankfurt Air India $553
Denver American Airlines $164
Orange County (Santa Ana) American Airlines $236
Krakow Air Canada $597
Madrid American Airlines $589
Jackson Hole American Airlines $261
Minneapolis St. Paul American Airlines $114
Riga Air Baltic $567

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