$50+ Cheap flights to Chicago, IL

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.

Peak Season: Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighborhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals. Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavors accompanied by live music. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers. September can be the most enjoyable and mild month of the year but there’s less going on during this period. Off-peak Season: January to March is when Chicago is least busy, making cheap flights to Chicago and hotel deals more 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.

Chicago is home to two major airports, O’Hare International and Midway International, and welcomes travelers from around the country on many major airlines. How long your flight will take depends upon your departure city with flights from Seattle, WA, and Los Angeles, CA, taking approximately four hours. Air travel from New York, NY, lasts approximately 2.5 hours, and you’ll spend a little less than three hours in the air if you’re flying in from Houston, TX.

Multiple airlines serve the two airports with Delta, Southwest and Volaris being among those that fly to Midway International and JetBlue, United and Spirit included in airlines that fly to O’Hare. International travelers can fly on a multitude of airlines into Chicago, including Lufthansa, Qatar Airways and Emirates.

Because Chicago experiences all four seasons to their fullest, you’ll want to pack according to the time you choose to visit. Late spring and summer are typically warm, calling for shorts and light tops. Bring your walking shoes to walk along the shores of Lake Michigan. Fall offers beautiful color and crisp days that can turn rather chilly as evening descends. Pack clothing that is easily layered so that you can adjust as the temperature does. Winter in the Chicago area can be pretty brutal, with windy days, snow and below-freezing temperatures. Before you zip your suitcase, make sure you’ve brought along extra socks, gloves, a hat and scarf to ward off the worst of the winter weather.

There’s never a shortage of things to do no matter what time of year you choose to visit Chicago. Visitors at Christmastime don’t want to miss a stroll down the Miracle Mile with its high-end shops and upscale dining experiences. Top the evening off with a visit to 360 Chicago at the top of the John Hancock building. The thrilling attraction offers breathtaking views of the city along with Tilt, a one-of-a-kind observation cube that moves you out over the streets from 1,000 feet up. Chicago’s lakefront offers beautiful views of Lake Michigan along with immersive educational experiences that are made for the entire family to enjoy. Begin your day at the Museum of Science and Industry and take a ride down into a replica coal mine or explore a German U-boat. The hands-on museum offers a little bit of something for everyone. Spend the afternoon in the Lincoln Park Zoo, which is free to the public and offers a range of animals to enthrall your youngsters, from reptiles to gorillas. If baseball is your passion, no trip to Chicago is complete without a trip to Wrigley Field for a game in the spring or summer. The park has been hosting fans of the Cubs and their opponents for over 100 years.

Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

Based on reviews from Cheapflights users, Spirit Airlines is rated the highest out of the airlines that fly to Chicago.

Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost $34, while round-trip flights cost around $50.

A round-trip flight to Chicago will typically cost around $1,387, however they can be found for as little as $68.

For those looking to save time traveling to Chicago, Muskegon offers the quickest one-way flight (0 hours 50 minutes).

If being close to Aragon Ballroom is important to you, you’ll want to land at Chicago O'Hare Intl Airport.

Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.

Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 mi away from Chicago O'Hare Intl).