Southwest® flights to Chicago (O'Hare) starting at $49

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Flights to Chicago O’Hare (ORD) Airport 

Chicago O’Hare International Airport (ORD) is a major global aviation hub serving Chicagoland and the Midwest with regional, national, and international flights. Although ORD airport shares Chicago’s airspace with Chicago Midway International Airport, ORD is by far the bigger of the two—and yes, it's the airport you remember from Home Alone.

What to Know Before Flying to Chicago O’Hare

Entering the Chicago O'Hare arrivals area can be overwhelming at first—so, if you've got the time, stop in at one of the top-tier Chicago restaurants represented here. Chicago O’Hare is located on the city’s northwest side, as opposed to Chicago’s other airport, Midway, which is nestled in the city’s south side neighborhoods.

While O'Hare is slightly farther from downtown Chicago than Midway, the CTA Blue Line provides transit service straight from O’Hare 24 hours a day. It's often the fastest way to get from O'Hare to downtown Chicago. Prefer to drive? Chicago O’Hare parking and rental car services are both available onsite.

How to Find Cheap Flights to Chicago O’Hare

The number one hot tip for cheap flights to ORD: If you’ve got flexible travel plans, check the Southwest Low Fare Calendar to compare dates and find the hottest deals. Other ideas you might consider:

• Booking at off-peak times like early mornings or late at night
• Flying on days when demand tends to be lower (typically Tuesday or Wednesday)
• Booking as far in advance as possible to secure a more affordable flight

What is the Best Time to Visit Chicago?

Chicago in summer is the peak tourism season, and even locals tend to stick around for the gorgeous weather. Be ready for bigger crowds and more demand for flights if you're traveling in the summer. Chicago winter typically brings lower demand, but Cloud Gate—the famous metal sculpture commonly known as the Bean—looks just as beautiful under the snow as it does in the sunshine.

Best Food & Drink in Chicago

• Try a classic Italian beef sandwich, a thin-crust tavern-cut pizza, or a Chicago-style hot dog loaded with veggies – but never ketchup!
• Visit indoor exhibits at the Art Institute of Chicago
• Explore neighborhoods like Andersonville, Hyde Park, and Uptown for authentic global cuisines inspired by generations of immigrant communities.
• Don’t miss Chicago’s vibrant Restaurant Row, where top chefs and local favorites serve flavors from around the world.