With our cheap tickets to Chicago, your next weekend getaway is closer than ever. Whether you’re heading to the Windy City for a summer festival, a snowy winter getaway or just to get back to school for the semester, we’ve got cheap flights to Chicago for you. Prices on this page are updated daily, so bookmark this page or sign up for emails to keep an eye on these great deals.
Dreaming of a trip to the Windy City? Even if you only have a weekend, Chicago is one of the best cities in the US for a weekend trip (and if you have more time, there’s still plenty to do!). From selfies with the bean at Millennium Park to enjoying the views of the city from Willis Tower or Skydeck Chicago. Visit one of Chicago’s world-famous museums, take a food tour of the city (deep-dish pizza anyone?) or just hang out in one of the city’s many public parks and beaches and enjoy some summer sun.
For more info on the best time to visit Chicago, cheapest times to book your tickets and more, just keep scrolling. Ready to book? Search now to see our cheapest deals from your hometown or check out our latest promo codes for more savings.
Chicago has two major passenger airports: Chicago O’Hare International Airport and Chicago Midway Airport. Chicago O’Hare is slightly further from downtown Chicago, but is much larger and provides more flights; while Midway offers primarily domestic flights and is less crowded.
Chicago O'Hare: Chicago O’Hare is one of the busiest airports in the US and offers a huge number of both domestic and international flights to Chicago. Once you arrive, the Blue Line “L” train will take you from O’Hare to downtown Chicago in about 45 minutes. Tickets are about $5 and you can catch the train from Terminals 1, 2 and 3 at the O’Hare airport.
Chicago Midway: Chicago Midway is much smaller but still offers plenty of domestic flights. Since it’s less crowded and a bit closer to the city, it’s a popular choice for students and business travelers flying domestically. Once you’ve arrived, you can take the Orange Line “L” train to downtown Chicago in about 25 minutes. Taxis/Ubers are also an option and will take about 25 minutes to get downtown as well.
Chicago is well-connected to many other American cities. It’s a major hub for both American Airlines and United Airlines, as well as the budget airlines Frontier and Spirit, although of course, many other airlines fly to Chicago as well. You can fly nonstop to Chicago from most major cities in the US, and you’ll also find plenty of connecting flights from smaller cities as well.
Keep scrolling to find info on flights to Chicago from New York, Los Angeles, Boston and more.
Average flight duration
2.5 hours
Number of daily flights
about 150 nonstop flights daily.
Average flight duration
2 hours, 45 minutes
Number of daily flights
about 70 nonstop flights daily.
Average flight duration
4 hours
Number of daily flights
about 120 nonstop flights daily.
Average flight duration
2 hours
Number of daily flights
about 37 nonstop flights daily.
The best time to visit Chicago is typically late spring (April-May) or fall (September-early November). During these times, the weather is pretty mild and there are fewer crowds generally. Late spring and early summer also typically bring many festivals and events to Chicago, making it a great time to visit the city.
While winters in Chicago can be quite magical, the average temperature between December and February is 26°F, so be sure to bundle up if you’re traveling here in the winter!
Prices based on bookings made 31-60 days prior to departure.
Chicago is an incredible city, whether you’re staying for a weekend or moving here for university. It’s beautiful and clean, with museums, art, parks, beaches, thousands of amazing restaurants and a diverse population.
Chicago is home to several universities, both in central Chicago and further outside the city. The University of Chicago, University of Illinois in Chicago and Northwestern University are top-ranked schools in Chicago. All three of these campuses are located near downtown Chicago. Chicago is a great place for students—great universities, ample museums, art and culture and good public transportation.
Chicago is a fun place to be—especially in good weather! Chicagoans love to enjoy the warmer weather once it comes around, so you’ll find Chicago full of outdoor events, block parties, rooftop bars, concerts in parks and more during the summer months. Embrace the beaches and all the things to do downtown. Chicago is dense and diverse: make sure you give yourself plenty of time to explore! The people are friendly, the food—from the street food to high-end restaurants—is delicious, and the city is full of quirky traditions and fun events. Grab a bike or hop on the subway and get exploring!
Chicago is actually much more budget-friendly than most people realize, whether you’re just visiting or coming for university or work. Compared to other big cities in the US (like New York, LA or San Francisco), Chicago is a much cheaper place to live. Even if you’re just visiting, you’ll find the city very walkable and easy to bike around, so you won’t have to rent a car. There’s plenty of budget food options, from street food to budget-friendly restaurants or a good old-fashioned deep dish pizza. And there’s plenty of free things to do in Chicago as well, from museums to zoos to taking a selfie with the giant bean.
