Best Time to Fly to Chicago
Chicago’s seasons are intense – it’s hot in the summer and cold in the winter – but savvy travelers can always find cheap airline tickets to Chicago.
Summer is between June and August and it is the peak of the festival season in the Chicago area with major events taking place in the parks and neighborhoods every weekend, in spite of the heat and humidity from the Lake. September can be the most enjoyable and mild month of the year but there's less going on during this period.
January to March is when Chicago is least busy and deals on cheap hotels and flights are usually attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.
Why you should take a flight to Chicago
Chicago is a skyscraper metropolis. The Windy City is a feat of modern architecture and home to what was once the world’s tallest building, Sears Tower, Chicago may not be a traditional tourist destination but you will find that the Second City is well worth a visit. As the hub of the Midwest, Chicago is not to be overlooked. Its picturesque skyline is reflected in the waters of Lake Michigan. World-class museums of art and science, fine public art, huge parks and sandy beaches and a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups) make it an unbeatable destination for a holiday. First stop should be the lakefront, from Lakeview to Oak Street Beach, the entire area is bustling for things for you to do and to see. Whatever your passion, Chicago will match it.
One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don't expose skin to the wind; in summer, be sure to drink plenty of water.
Getting around Chicago
There are plenty of ways to get around Chicago: hop on the ‘L’ (short for elevated train), the city’s subway system, or one of the buses that runs all over the city. For information about fares and routes, check out the website for the Chicago Transit Authority. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Biking is a popular way to get around and with all of Chicago’s lakefront property, it can be a great way to enjoy the city.
Flight deals to Chicago
USA departure airports for flights to Chicago
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- New York (NYC)
- Houston (IAH)
- Dallas (DFW)
- Atlanta (ATL)
- Los Angeles (LAX)
- Phoenix (PHX)
- Minneapolis (MSP)
- Boston (BOS)
- Las Vegas (LAS)
- Denver (DEN)
- Washington (WAS)
- Philadelphia (PHL)
- Miami (MIA)
- San Francisco (SFO)
- San Diego (SAN)
- Seattle (SEA)
- Kansas City (MCI)
- Orlando (MCO)
- Tampa (TPA)
- Austin (AUS)
- Charlotte (CLT)
- San Antonio (SAT)
- New Orleans (MSY)
- Cleveland (CLE)
- Fort Lauderdale (FLL)
- Detroit (DTT)
- Memphis (MEM)
- St Louis (STL)
- Pittsburgh (PIT)
- Newark (EWR)
This is useful information about Chicago
More useful information about Chicago
- Compare last minute flights and travels deals from New York to Chicago.
- Visit the tallest building in the US – the Willis Tower – and walk around the Skydeck for breathtaking views.
- Buy a direct flight to Chicago and see sights like The Magnificent Mile, Millennium Park, and the Navy Pier.
- Experience the charm of deep dish pizza and cart-side sausages, and then dine at Chicago’s gourmet restaurants.
- In the summer, make sure to stroll through Grant Park, where free concerts and food festivals grace the urban outdoors.
- Chicago flights can either arrive at Chicago O'Hare or Midway airports.
- The first ever Ferris wheel was debuted at Chicago's 1893 World Columbian Exposition.
- Cultural tourist hot spots include the Art Institute of Chicago, Goodman Theatre, and the Civic Opera House.
- Chicago has a unique Lake Michigan view. Take a one way flight to enjoy it for an extended period of time.
- Shoppers head straight to State Street in the center of the Loop for both bargains and designer digs