$29 Cheap flights from Chicago, IL

This week, flights from Chicago are available between $58 – $296.

Expedia makes it easy to compare cheap flights from Chicago to many destinations. Check out excellent deals on domestic and international flights from Chicago. Once you select an offer, use our filters and sort by “Price (Lowest)” to see some of the cheapest and suitable options.

On Expedia, you have some of best airline ticket deals at your fingertips. Whether it’s a beach escape with your partner, a family vacation with your kids, or business trip with colleagues, these low airline ticket prices mean more savings for you. An excellent strategy for finding some of the best deals on flights from Chicago is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our “Show flexible dates” feature. Depending on your destination, direct flights from Chicago may be more expensive. Airlines with strict bag policies or fees can also impact your costs.

At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Chicago with: Frontier Airlines, Southwest Airlines, American Airlines, Sun Country Airlines, Volaris.

One of the cheapest times to fly from Chicago airport(s) is February, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand.

Expedia is the place to find last-minute flights from Chicago, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source some of the best deals for you and display some of the best offers available over the next 2 weeks.

Booking flights from Chicago with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you some of the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from, so you can find some of the cheapest flights from Chicago. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more.

Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our customer service portal. We recommend choosing flights with no change fees for the most flexibility. Filter by “Flexible change policies” to see flights with no change fees.