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Cheap Flights from Chicago

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Top Airlines Offering the Cheapest Flights from Chicago

With numerous carriers operating out of Chicago, the competition is fierce – and that’s good news for those hunting for deals. Here are some of the top airlines offering budget-friendly flights from Chicago:

Find Major Airports in Chicago

Chicago is home to some of the nation’s busiest airports. Offering domestic and international flights, these airports connect the Windy City to the world: 

As one of the busiest airports globally, O’Hare International Airport offers unparalleled access to destinations worldwide. With four passenger terminals and a vast array of airlines, it’s the biggest airport in Chicago.

Midway International Airport is a favorite among travelers because it offers numerous domestic flights and a select number of international routes. It’s an excellent alternative to O’Hare as they service more cheap flights from Chicago.

A hidden gem just outside Chicago, Chicago Rockford International Airport provides domestic flights and limited international service. This airport is great for savvy travelers looking to avoid large crowds.

Just over the state line in Indiana, Gary/Chicago International Airport  serves as a reliever airport for O’Hare and Midway. It’s an option for those who prioritize ease and simplicity in their travel experience.

Discover Your Next Adventure from Chicago

In the last six months, OneAir has unlocked the lowest deals for our members departing from Chicago, connecting them to exciting destinations worldwide. Explore the most affordable flight options to each of these incredible places.

Flights from Chicago Snapshot

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Total number of deals from Chicago in the last month


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The Cheapest Time to Fly from Chicago

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Most Expensive Months to Fly

Jul and Dec

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Cheapest months to fly


Frequently Asked Questions

The cheapest months to fly from Chicago are October to November, while July and December are the priciest. However, these are just averages. Prices can vary significantly based on factors such as the airline and how far in advance you book.

The cheapest flights from Chicago to Europe can vary based on several factors, including which airport you’ll fly to. Regular roundtrip fares from Chicago to Europe can often climb from $1,200 to $1,500 during peak season, but you can score deals under $700 during off-peak season.

Sign up for a OneAir membership to help you find the best prices and compare flights between different airlines. Remember, flexibility with your travel dates can also lead to bigger savings.

When flying out of Chicago, you have two major options: O’Hare International Airport (ORD) and Midway International Airport (MDW). If you prioritize a wide array of flight options and don’t mind a larger, busier airport, O’Hare could be the best fit. Alternatively, if you value convenience and efficiency, Midway might be your airport of choice.

In terms of airlines, United Airlines and American Airlines are the two carriers with the most flights out of Chicago, particularly from O’Hare. Both airlines offer domestic and international flights from Chicago.

With approximately 858 daily direct flights to other US cities, you won’t have difficulty finding nonstop flights from Chicago. Fly from O’Hare and hop on cheap flights to popular local destinations like New York City, Dallas, Los Angeles, Las Vegas, Phoenix, Charlotte, or Washington D.C.

Travelers have the convenience of accessing direct flights to a multitude of direct flights from Chicago to Europe. Renowned airlines like KLM, United, LOT Polish Airlines, SAS, Aer Lingus, Lufthansa, Turkish Airlines, Norwegian Air, American Airlines, British Airways, Air France, Icelandair, Austrian Airlines, and SWISS operate these nonstop routes.

Flights from Chicago to London take approximately 10 hours and 15 minutes with one stop. Prices are lower in April, the cheapest being $530 for roundtrip economy tickets with Iceland Air.

Flights from Chicago to Rome take approximately 15 hours with one stop. Prices are lower in February, the cheapest being $896 for roundtrip economy tickets with Turkish Airlines.

San Juan, Puerto Rico is the cheapest international destination from Chicago, with roundtrip tickets for as low as $207 via Frontier. Planning your trip for early February is recommended to secure the best deals, as this timeframe tends to offer the most budget-friendly fares.

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