Cheap air tickets to Chicago

Compare Chicago flights across hundreds of providers

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals to Chicago

Looking for a cheap last-minute deal or the best return flight to Chicago? Find the biggest savings on one-way and return tickets right here.

Find the cheapest time to fly to Chicago

Flexible on travel dates? Find the cheapest month – or even day – to fly to Chicago.

Airports in Chicago

Looking for the best route? There are 4 airports in and around Chicago.

Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
Currently, there are no airlines that fly direct to Chicago. But we found flights with one or more stops from $1,349.
The cheapest month to fly to Chicago is usually October.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
No airlines currently offer direct flights between Singapore and United States. Most routes have one or more stops.
The best price we found for a return flight to Chicago is $1,349. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
The cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $1,349.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago is Tuesday, 15 October 2024.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
The average temperature in Chicago in April is around 8°C. The warmest month in Chicago is typically July, which averages 26°C. The coolest month is January, with temperatures averaging -8°C. The rainiest month is August, and it usually rains the least in January.
Currently, EVA Air offers the cheapest flight tickets to Chicago.

Flying to Chicago

The things to know before you go.
Cheapest flight found$1,349
Cheapest month to flyOctober
Average flights per week0

Discover Chicago

How to find cheap flights to Chicago

Looking for cheap air tickets to Chicago? Whether you are aiming to find one-way or return flights, here are a few tips on how to secure the flight fare and make your journey as smooth as possible.

  • Simply hit 'search'. We've compared plane tickets from all major online travel agents and airlines flying to Chicago to find the cheapest flights. And with us there are no hidden fees - what you see is what you pay.

  • Be flexible with your dates to find the best air ticket price for your Chicago flight. If your travel dates are flexible, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from your chosen departure location.

  • Set up a Price Alert. You can easily track the price of your cheap flights to Chicago by creating an alert. Whenever fares go down or up, you'll get a push notification or e-mail to help you get the best flight offer.

  • Look for non-stop flights. Only interested in direct flights to Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct Chicago flights available, these will appear in the results.

  • Include nearby airports in your search. Widen your search for Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save on your next trip.

  • Find the cheapest Business class flights to Chicago. Check the difference in price of your plane ticket to Chicago when travelling in Economy, Premium economy, Business or First class. Note that not all cabin classes are available for every destination or airline.

  • Search for cheap flights when out and about. To get the best flight booking experience on the go, download our app and search for flight tickets to Chicago wherever you are.

Book air tickets to Chicago with peace of mind

  • Find flexible flights to Chicago. Your airline might be offering flexible plane tickets to Chicago, which means you won't lose out if your flight has to be changed or cancelled.

  • Add travel cost protection. Avoid travel pitfalls and choose travel cost protection - it's available at the checkout as you book your flight to Chicago with us.

  • Reduce your carbon footprint by selecting a greener Chicago flight option. To check whether there are any lower emissions flights available on your route, simply check the “only show flights with lower CO₂ emissions” box which will be available once you have moved on from this page.

Combine your flight to Chicago with hotels and car hire

Once you've secured your plane ticket to Chicago, we will help you discover the best prices and exclusive rates for hotels in Chicago or nearby. We also allow you to compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.

Compare Chicago tickets with other destinations using the everywhere search

Not entirely set on flying to Chicago yet? You can easily browse other destinations by searching flights to 'Everywhere' - this will allow you to find the cheapest place to travel from your departure point.


More travel options

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.