Cheap Flights to Chicago

Compare Chicago flights across hundreds of providers

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

Book the best Chicago fare with no extra fees

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.

Airports in Chicago

Compare routes to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier.

Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

Which airlines offer direct flights to Chicago?

Currently, there are no airlines that fly direct to Chicago. But we found flights with one or more stops from £688.

When is the cheapest time to fly to Chicago?

The cheapest month to fly to Chicago is usually May.

How can I find the best flight deal to Chicago?

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.

How much are return flights to Chicago?

The best price we found for a return flight to Chicago is £688. 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.

Which is the cheapest airport in Chicago?

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 £688.

Which upcoming date is cheapest to fly to Chicago on?

After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago is Saturday, 10 May 2025.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

The average temperature in Chicago in March is around 3°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.

Which is the cheapest airline to fly to Chicago with?

Currently, Aurigny offers the cheapest flight tickets to Chicago.

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How to find cheap flights to Chicago

Looking for cheap tickets to Chicago? Here are a few tips on how to score the best price 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.
Flex your dates to secure 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 time to fly to Chicago.
Set up a Price Alert. You can easily track the fare of your flights to Chicago by creating an alert. Whenever prices go down or up, you'll get a push notification or e-mail to help you get the best flight deal.
Compare flight deals to Chicago from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
Look for direct 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.
Find the cheapest Business class flights to Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare.
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 next time you travel.

Combine your flight to Chicago with hotels and car hire

Once you've secured your cheap flight ticket to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.

Compare Chicago plane tickets with other destinations using the everywhere search

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