Cheap Flights To Chicago
Destination Profile
Chicago mingles the gritty and the majestic. From The Loop's Art Deco skyscrapers all the way to the jalapeno-sizzling taquerias of Pilsen and the roaring baseball terraces of Wrigleyville, it's a metropolis that lurches from the grand to the lived-in with ease and enjoyment. Yes, you can see priceless paintings in the Art Institute of Chicago and be stunned by the views from the top of Willis Tower. But you can also spend days searching for grilled saganaki in Greektown or deep-pan pizzas in Little Italy. Cheap flights to Chicago typically come into either Chicago O'Hare or Midway Airport. They come from all over the United States, not to mention stacks of long-haul destinations across the Americas, Europe, Asia, and Africa.
Top sights In Chicago
Millennium Park
Open-air pavilions and cutting-edge sculptures sit in the buzzing entertainment area of Millennium Park.
Willis Tower
Once the tallest tower on the globe, the Willis Tower now hosts lookout points with some of the greatest views of Chicago.
Lake Michigan
Take a boat ride out to Lake Michigan to whiz past Grant Park and the see the skyline of the Windy City in all its glory.
Questions & Answers
What is the cheapest month to fly to Chicago?
At the moment, November/2025 is the cheapest time of year to take a flight to Chicago.
What airlines fly direct to Chicago?
Delta, United, Alaska Airlines, Southwest and American Airlines have direct flights to Chicago.
What is the cheapest airline to fly to Chicago?
Frontier is the cheapest airline that flies to Chicago.
What is the best airline to fly to Chicago?
Delta is the best airline to fly to Chicago and it flies non-stop. JetBlue is the best budget airline.