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Chicago O'Hare is one of the world's busiest airports and a major hub for both United and American Airlines. Midway serves as Southwest's largest hub, offering competitive domestic fares.
January through March (excluding spring break) offers the best deals from Chicago.
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How do I find the cheapest flights from Chicago?
The easiest way to find cheap flights from Chicago is to subscribe to Friday Flight Deals. We monitor prices across all major airlines and send you the best deals every Friday. You can also compare prices across O'Hare (ORD), Midway (MDW) as fares can vary significantly between airports.
When is the best time to book flights from Chicago?
January through March (excluding spring break) offers the best deals from Chicago. We recommend booking 6-8 weeks in advance for domestic flights and 2-3 months ahead for international travel. Being flexible with your dates can save you hundreds on airfare from Chicago.
Which airports serve Chicago?
Chicago is served by O'Hare (ORD), Midway (MDW). Comparing prices across all airports can help you find better deals, as budget carriers and different airlines often have varying prices at each airport.
Are the flight deals from Chicago legitimate?
Yes! All deals we share are manually verified before publishing. We only feature genuine savings from Chicago airports on reputable airlines. Deals are typically available for a limited time, so we recommend booking quickly when you see a fare you like.
How often do you post new deals from Chicago?
We curate and publish flight deals every Friday. Subscribe to our newsletter to get Chicagoflight deals delivered directly to your inbox. We focus on quality over quantity, only sharing deals that represent genuine savings.
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