Cheap Flights from Waterloo to Chicago

Roundtrip selected

origin

Enter the city you're flying from, or choose from the options below

Include nearby airports

selected

destination

. Enter your destination, or choose from the options below

Include nearby airports

selected

Travelers and cabin class, 1 Adult, Economy

Compare Waterloo to Chicago flight deals

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 Cheapest month Find the best route Route info FAQs Tips and advice

Flight deals from Waterloo to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Waterloo to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

Chicago.AED 745 per passenger.Departing Sun, Dec 6, returning Mon, Jan 11.Round-trip flight with American Airlines.Outbound direct flight with American Airlines departing from Waterloo on Sun, Dec 6, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departing from Chicago O'Hare International on Mon, Jan 11, arriving in Waterloo.Price includes taxes and charges.From AED 745, select.

Direct flights from Waterloo to Chicago

Alternative Waterloo to Chicago routes

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

Waterloo to Chicago: Flight information

The things to know before you go.

Average flight time	1 hr, 36 mins
Most popular airline	American Airlines
Average flights per week	47

Finding cheap flights from Waterloo to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.

How much are round-trip flights from Waterloo to Chicago?

The best price we found for a round-trip flight from Waterloo to Chicago is AED 745. 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.

How long does it take to fly from Waterloo to Chicago?

1 hour and 36 minutes is the average flight time from Waterloo to Chicago.

Which airlines fly direct from Waterloo to Chicago?

American Airlines, Qatar Airways and SkyWest Airlines fly direct from Waterloo to Chicago.

How many flights are there a week from Waterloo to Chicago?

There are 47 flights per week flying from Waterloo to Chicago, as of October 2026.

When is the cheapest time to fly from Waterloo to Chicago?

The cheapest month to fly from Waterloo to Chicago is usually December.

What's the cheapest airport to fly to in Chicago?

If you're flying from Waterloo Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.5 km away from the center of Chicago. We've found flights to this airport from AED 745.

Which upcoming date is cheapest to fly from Waterloo Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Waterloo Airport to Chicago on Sunday, December 6, 2026.

Can I get a direct flight from Waterloo Airport to Chicago?

Yes – the average flight time is 1 hour and 36 minutes.

How can I get the best flight deal from Waterloo Airport 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.

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?

In October, the average temperature is usually around 14°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.

Which is the cheapest airline to fly with from Waterloo Airport to Chicago?

Currently, American Airlines offers the cheapest flight tickets to Chicago.

How to find cheap flights from Waterloo to Chicago

Looking for cheap flight tickets from Waterloo to Chicago? Skyscanner compares flight prices across more than 1,200 airlines and travel providers.

Regardless of whether you're looking for a one-way ticket to Chicago or a return flight, here are some tips to secure the best flight price and make planning your journey as smooth as possible.

Simply hit search. From Emirates and Etihad to international carriers like Air India and Wizz Air, we compare all major airlines with the most popular online travel agents to find the cheapest plane tickets from Waterloo to Chicago. And with us there are no hidden fees - what you see is what you pay.

Flex your dates to find the cheapest ALO - CHIA flight tickets on Skyscanner. Search for flights but don’t enter the departure date and instead click ‘whole month’. This tool will find the cheapest month and dates to fly to Chicago from Waterloo.

Set up a Price Alert for Waterloo-Chicago flight tickets. You can easily track the fare of flights by creating an alert. Whenever prices go down or up, you'll get an email to help make sure you get the best possible flight deal. Or download our app and get price alerts straight to your phone.

Fly without stops. Only interested in direct flights between Waterloo and Chicago? Make sure to tick 'Non-stop flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.

Hotels in Chicago

Looking for a hotel in Chicago? Whether you’re looking for a local hotel or a global brand, discover the best prices and exclusive rates for hotels in Chicago by comparing the biggest names in travel.

Car hire in Chicago

If you’re looking for car rental in Chicago, we can help you uncover the best car hire deals. We search hundreds of car hire companies allowing you to instantly compare prices and then book.

Book flight tickets from Waterloo to Chicago with extra peace of mind

Back in 2020, most airlines introduced policies to make travel during COVID-19 as easy as possible. The worst of the pandemic is now over, but some of these policies remain in place for you to take advantage of as you step back out into the world.

Find flexible getaways. Some airlines introduced flexible booking policies in 2020 – and many of these are still available. If you book a flexible plane ticket from Waterloo to Chicago, it means your money is still safe if your flights are changed or cancelled due to COVID-19.

Get insured. Choose travel cost protection that covers COVID-19, too. It's available at the checkout as you book your flight from Waterloo to Chicago with us.

Plan the rest of your trip from Waterloo to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.