Cheap flights to Chicago

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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

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

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 P41,301.
The cheapest month to fly to Chicago is usually December.
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 Philippines and Chicago. Most routes have one or more stops.
The best price we found for a return flight to Chicago is P41,301. 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 P41,301.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago is Friday, 5 December 2025.
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 June is around 19°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, Korean Air offers the cheapest flight tickets to Chicago.

Flying to Chicago

The things to know before you go.
Cheapest flight foundP41,301
Cheapest month to flyDecember

Discover Chicago

How to find cheap flights to Chicago

  • P41,301 is currently the cheapest price we've found for a return flight to Chicago. For a one-way ticket, the lowest fare is P24,465.

  • Book at the perfect time with Price Alerts. You'll receive an email or a notification on the app if Chicago ticket prices change.

  • To get cheap tickets to Chicago, book six months before you travel. That's the general recommendation for scoring the best bargains.

  • Broaden your search for cheap Chicago flights by selecting the 'Add nearby airports' box. You'll see fares for surrounding airports which could offer bigger savings.

  • If you aren't in a rush to get to the city, think about taking a scenic route. You might find cheaper Chicago plane tickets by booking a flight with one or more stops.

Best time to go to Chicago

  • The cheapest month to jump on a flight to Chicago is usually May.

  • To find the month with the cheapest Chicago flights, use the 'Whole month' tool. If you have flexible travel dates, keep an eye out for the green prices on the calendar — they show you the lowest fares that are available.

  • If you'd like to experience the city at its liveliest, lock in your flights to Chicago for August. Being on holiday during high seasons generally means there's more to see and do than at other times of the year.

  • The quietest time of the year to go is January. Book your Chicago plane tickets then and enjoy sightseeing at a slower pace.

  • With averages between 15ºC (59ºF) and 29ºC (84ºF), July is when Chicago is at its warmest. Organise your visit around your weather preferences to get the most out of your trip.

  • January has the lowest temperatures, ranging from about -12ºC (10ºF) to 3ºC (37ºF).

Travelling to Chicago: what you need to know

Getting to central Chicago from O'Hare International Airport (ORD)

Chicago highlights

  • Put these popular attractions at the top of your to-do list after stepping off your flight to Chicago:

    • Millennium Park

    • Art Institute of Chicago

    • LandShark Beer Garden at Navy Pier

Complete your trip with a Chicago car hire

Choose one of our car rentals in Chicago and take in the sights at your own pace. Easily compare rates in one place to find the ideal ride after you've reserved your hotel and cheap flight to Chicago.

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