Heads up, deal hunters! If you're itching for a trip to or from the Windy City, now's the time to pounce. The Flight Deal has spotted some seriously low fares – we're talking as low as $185 for a roundtrip! To snag these prices, you'll need to use Matrix Airfare Search by ITA Software. Don't let the name intimidate you; it's a powerful tool that lets you find the cheapest flights. Just punch in your origin and destination (Chicago, or to Chicago), and let it work its magic. Why should you care? Well, besides saving a ton of money on your flight, a cheap base fare frees up your travel budget for amazing food, shows, or even a nicer hotel. Keep in mind that these fares are for regular economy, so you might have to pay extra for things like checked bags or seat selection. Still, at these prices, it's a steal!