Cheap flights from Chicago to anywhere

This month, the top selected destinations from Chicago are Atlanta, Boston, Athens. Throughout the year, Atlanta, Boston, Mumbai are some of the top choices made by users flying from Chicago.

We've found Milwaukee, South Bend, and Bloomington as options for shorter direct flights within 108 km of Chicago. These locations can be great options for travelers looking to go somewhere and back quickly.

Greensboro, Hong Kong, and Taipei City are the furthest destinations available from Chicago.

From Chicago you can expect to find greater availability for the following destinations: New York (1,877 flights per day), Detroit (922 flights per day) and Los Angeles (647 flights per day).

View the cheapest flight destinations from Chicago:
Fly from Chicago to Singapore from S$ 1,221 round trip

When flying from Chicago check dates and pricing for the following: Delta, United Airlines. As they depart for the following popular destinations: Singapore.

Those who are seeking the cheapest fare on flights departing from Chicago would be wise to consider leaving during Thursday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Saturday afternoons when fares are usually the most expensive.

The price you pay for your flight from Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 2 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

When you search for this flight from Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the best flight for you.

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

Users can book flights with no change fees policies with our dedicated filters. Book flights from Chicago flexibly with Cheapflights today.

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.