Cheap Flights To Chicago - From $391 Return
from $391
Flights to Chicago from $391 Return
29 August, 2026
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, the most affordable time of year to fly to Chicago is January/2027. You will pay the most in August/2026.
What airlines fly direct to Chicago?
United, Southwest, American Airlines and Spirit Airlines fly non-stop to Chicago.
What is the cheapest airline to fly to Chicago?
The cheapest airline to fly to Chicago is Delta.
What is the best airline to fly to Chicago?
Qatar Airways is the best airline to fly to Chicago. United is the best if you would like non-stop flights. JetBlue is the best budget airline.