Cheap flights to Chicago, IL

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.

How long is the flight to Chicago?

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.

Chicago Travel Guide

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.

Getting to and around the city of Chicago

Flights to Chicago land at O’Hare International Airport (ORD) located in the city’s northwest corner, about 17 miles away from the CBD or Chicago Loop. Trains and buses provide efficient transportation to city center and suburbs. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available from the airport.

Tips for your stay in Chicago

• Chicago is a big and busy city, and you’ll want to stay aware of your surroundings to keep yourself and your family and friends safe. Keep purses and valuables close to your person, or better yet, leave them in an in-room safe before you head out for the day.
• Security at Chicago’s attraction is generally a given, and your bags and belongings will be searched, making this another good reason to travel lightly as you tour the city’s treasures.
• Traffic throughout the Chicago area is heavy, with rush hour lasting basically throughout the day. Consider budgeting a taxi into your visit or use the subway to get around town.
• There’s a lot to see when you visit Chicago, and you’ll want to plan your days accordingly. Consider investing in a Go Chicago pass, which lets you add the attractions to one convenient card that saves you money on admissions.

Finding Flights from Chicago

Chicago O’Hare International airport is among the country’s busiest airports and, along with Midway International airport, sees millions of passengers off each year. Both airports are served by many of the world’s largest airlines, including American, United, Delta, KLM, Lufthansa and Emirates, offering flights across the country and around the world. Searching Cheapflights for your next flight out of Chicago puts you in touch with great fares.

Keeping with the airports’ busy daily schedules, arriving early for your flight is a must. Leave time to make it through the baggage claim and security and arrive at your gate before the boarding call. International travelers should be aware that security can take longer and plan with that in mind.

CTA trains serve both O’Hare and Midway and are the most cost-effective way to get to the airport if you haven’t rented a car. The Blue Line gets you from downtown Chicago to O’Hare, while the Orange Line will get you from downtown to Midway. Make sure to leave enough time for delays.

If you’re looking to learn more about Chicago’s airports before you book your flight, check out our Chicago Airport Guides for more detailed information on airlines, terminals and other important must-know travel information.