Cheap flights from Chicago starting at S$115

This week, flights from Chicago are available between S$254–S$406. 

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

Expedia gives you access to all the hottest deals on plane tickets so you can get the most amount of value for the lowest price possible. An excellent strategy for finding the best deal on flights is to be flexible with your dates. For each offer, you can compare prices for similar time frames 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: Delta, American Airlines, United, avianca, Arajet, JetBlue Airways. 

Prices on plane tickets vary considerably throughout the year due to seasonal demand. Historically, the cheapest time to buy flights from Chicago airport(s) is February. 

ARC & Expedia Group historical data suggests that booking flights three weeks before departure and on a weekend, usually on a Sunday, can save you up to 20% on your fare. *

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 the best deals for you and display the best offers available over the next two weeks. 

Booking flights from Chicago with Expedia is the obvious choice to get low prices, save money and see more value for every pound spent. We show you the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from. You can customise your journey to your timeline, route preferences, budget, rewards programmes and more. Not only will you get a stellar deal, but you’ll also get rewards points back and the opportunity for additional discounts when bundling with a hotel or car hire.

Some flights can be changed or cancelled, 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 maximum flexibility. Filter by “Flexible change policies” to see flights with no change fees.