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664 € Cheap Flights from The Valley to Chicago

Compare The Valley to Chicago flight deals

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

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Flight deals from The Valley to Chicago

Looking for a cheap last-minute deal or the best return flight from The Valley Airport to Chicago? If you want to travel next month, return fares start from 664 €. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from The Valley to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like The Valley to Chicago flights are currently cheapest in May.
Apr
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May
from 664 €
Jun
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Jul
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Aug
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Sep
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Oct
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Nov
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Dec
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Jan
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Feb
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Mar
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Alternative The Valley to Chicago routes

Looking for the cheapest, fastest or easiest route from The Valley to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
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Chicago O'Hare International

25km from central Chicago
Cheapest
from 664 €
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Chicago Dupage County

51km from central Chicago
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Chicago Rockford

126km from central Chicago
Search flights

Finding cheap flights from The Valley to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from The Valley to Chicago is 664 €. 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.
Currently, there are no airlines that fly direct from The Valley to Chicago. But we found flights with one or more stops from 664 €.
As of April 2026, there are no flights flying from The Valley to Chicago.
The cheapest month to fly from The Valley to Chicago is usually May.
If you're flying from The Valley Airport, 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 664 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from The Valley Airport to Chicago on Wednesday, 20 May 2026.
No airlines currently offer direct flights between The Valley Airport and Chicago. Most routes have one or more stops.
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.
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.
In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Anguilla Air Services offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from The Valley

Looking for cheap tickets from The Valley to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

  • Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from The Valley to Chicago. And with us there are no hidden fees - what you see is what you pay.
  • Compare flight deals to Chicago from The Valley from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
  • Flex your dates to find the best The Valley-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from The Valley.
  • Set up a Price Alert. You can easily track the fare of your cheap The Valley-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Fly without stops. Only interested in direct flights between The Valley and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
  • Find the cheapest Business class flights from The Valley and 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. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for The Valley to 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 from The Valley with hotels and car hire

    Once you've secured your cheap flight ticket from The Valley 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.


Plan the rest of your trip from The Valley to Chicago

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