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Scheduled flights to Chicago

Here are all the scheduled flights to Chicago, providing a variety of convenient travel options.

Wed, 13 Aug 2025 (Today)

Thu, 14 Aug 2025

Fri, 15 Aug 2025

Airline	Departure Time	Arrival Time	Origin Airport	Destination Airport
Southwest Airlines	06:10	12:05	Los Angeles (LAX)	Chicago (MDW)	Book Flight
Southwest Airlines	09:00	10:25	New York (LGA)	Chicago (MDW)	Book Flight
Southwest Airlines	11:25	12:50	New York (LGA)	Chicago (MDW)	Book Flight
Southwest Airlines	13:10	19:05	Los Angeles (LAX)	Chicago (MDW)	Book Flight
Southwest Airlines	14:10	15:35	New York (LGA)	Chicago (MDW)	Book Flight
Southwest Airlines	15:35	17:05	New York (LGA)	Chicago (MDW)	Book Flight
Southwest Airlines	16:40	22:40	Los Angeles (LAX)	Chicago (MDW)	Book Flight
Southwest Airlines	17:50	19:20	New York (LGA)	Chicago (MDW)	Book Flight
Southwest Airlines	21:35	22:55	New York (LGA)	Chicago (MDW)	Book Flight
Southwest Airlines	23:15	05:10 (+1 day)	Los Angeles (LAX)	Chicago (MDW)	Book Flight

Airlines flying to Chicago

These airlines airlines offer direct service to Chicago.

Whether you're travelling from within Australia or from a destination abroad, these airlines offer direct service to Chicago. Select your preferred airline to learn more about what they can offer, including baggage information, seat classes, availability of lounges and frequent flyer programs.

Southwest Airlines

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Delta Airlines

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Frequently asked questions about flights

How do I book flight tickets to Chicago via Traveloka?

You can easily book your flight to Chicago with the search tool at the top of this page. Start by selecting your departure city and Chicago and choosing your travel dates. You'll then be presented with all the available flight options to Chicago, with the chance to filter by direct flights only, airline including baggage, departure times and even preferred stopover cities for connecting flights.

When is the best time to book a flight to Chicago?

If you're flying to Chicago from outside the country, then it's best to book three to six months in advance. For domestic flights, the earlier, the better, but six to eight weeks in advance on popular routes should do the trick. It's a good idea to keep an eye out for regular flight sales, like the EOFY, Black Friday and Boxing Day sales as this is when some of the best fares are available.

How can I get $50 off my flight to Chicago?

Until 31 July, you can save $50 off flights by using the code WINTERSALE50.