$350 Cheap Flights from Waterloo (ALO) to Chicago (ORD)

View $350 flight on Wed, Apr 30, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Waterloo to Chicago (ALO-ORD)

Prices were available within the past 7 days and start at $350 for one-way flights and $337 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 2 - Sat, Aug 9
ALO
Waterloo
ORD
Chicago
$337 Roundtrip, found 2 hours ago
$337
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Aug 2 from Waterloo to Chicago, returning Sat, Aug 9, priced at $337 found 2 hours ago
American Airlines
Sat, Jul 12 - Sun, Jul 13
ALO
Waterloo
ORD
Chicago
$354 Roundtrip, found 19 hours ago
$354
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Jul 12 from Waterloo to Chicago, returning Sun, Jul 13, priced at $354 found 19 hours ago
American Airlines
Thu, Jul 17 - Mon, Jul 21
ALO
Waterloo
ORD
Chicago
$371 Roundtrip, found 1 hour ago
$371
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Jul 17 from Waterloo to Chicago, returning Mon, Jul 21, priced at $371 found 1 hour ago
American Airlines
Sat, Oct 4 - Sun, Oct 19
ALO
Waterloo
ORD
Chicago
$394 Roundtrip, found 3 days ago
$394
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Oct 4 from Waterloo to Chicago, returning Sun, Oct 19, priced at $394 found 3 days ago
American Airlines
Sat, Aug 2 - Sat, Aug 9
ALO
Waterloo
ORD
Chicago
$397 Roundtrip, found 2 hours ago
$397
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Sat, Aug 2 from Waterloo to Chicago, returning Sat, Aug 9, priced at $397 found 2 hours ago
American Airlines
Fri, Sep 19 - Sun, Oct 19
ALO
Waterloo
ORD
Chicago
$411 Roundtrip, found 4 days ago
$411
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Sep 19 from Waterloo to Chicago, returning Sun, Oct 19, priced at $411 found 4 days ago
American Airlines
Sat, Jul 12 - Sun, Jul 13
ALO
Waterloo
ORD
Chicago
$414 Roundtrip, found 19 hours ago
$414
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Jul 12 from Waterloo to Chicago, returning Sun, Jul 13, priced at $414 found 19 hours ago
American Airlines
Tue, Apr 29 - Tue, May 27
ALO
Waterloo
ORD
Chicago
$422 Roundtrip, found 2 days ago
$422
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Apr 29 from Waterloo to Chicago, returning Tue, May 27, priced at $422 found 2 days ago
American Airlines
Wed, May 7 - Wed, May 14
ALO
Waterloo
ORD
Chicago
$423 Roundtrip, found 4 days ago
$423
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, May 7 from Waterloo to Chicago, returning Wed, May 14, priced at $423 found 4 days ago
American Airlines
Thu, Jul 17 - Mon, Jul 21
ALO
Waterloo
ORD
Chicago
$431 Roundtrip, found 1 hour ago
$431
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Jul 17 from Waterloo to Chicago, returning Mon, Jul 21, priced at $431 found 1 hour ago
American Airlines
Sun, Sep 7 - Wed, Sep 17
ALO
Waterloo
ORD
Chicago
$434 Roundtrip, found 2 days ago
$434
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sun, Sep 7 from Waterloo to Chicago, returning Wed, Sep 17, priced at $434 found 2 days ago
American Airlines
Tue, Apr 29 - Mon, May 26
ALO
Waterloo
ORD
Chicago
$439 Roundtrip, found 2 days ago
$439
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Apr 29 from Waterloo to Chicago, returning Mon, May 26, priced at $439 found 2 days ago
Flights from Waterloo (ALO) to Chicago (ORD)
Origin airport
Waterloo Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines
Roundtrip price
$337
Distance
233 mi

Waterloo to Chicago Flights

The cheapest times to fly from Waterloo to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Waterloo to Chicago are during the month of August. You can find some of the cheapest flights from Waterloo to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Waterloo to Chicago

Sunday is one of the best days to book for cheap flights from Waterloo to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Waterloo to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Waterloo to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $350 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Waterloo to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Waterloo to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD) cost?
You can score cheap return tickets from Waterloo Regional Airport (ALO) to O’Hare Intl. Airport (ORD) starting at $337. Reserve your seat and start your adventure. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a American Airlines flight leaving ALO on May 8 2025 and touching down at ORD. The price was last updated on April 27 2025 and has not changed since.
What is the cheapest month to fly from ALO to ORD?
The cheapest flights from ALO to ORD are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
Catch a nonstop flight with American Airlines and journey straight from Waterloo Regional Airport (ALO) to O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from ALO to ORD?
Currently, the cheapest carrier offering one-way flights from ALO to ORD is American Airlines. You can jet off on this route from $350. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ALO on May 7 2025. Prices were last updated on April 27 2025 and have not changed since.
How many flights per day from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
On average, there’s only 1 nonstop flight leaving from Waterloo Regional Airport (ALO) to O’Hare Intl. Airport (ORD) each day. If this isn’t convenient for you, think about flights with a layover. Just filter your search on Expedia to include one or two stops to find the next best option.
What are the most popular departure times for flights from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
The 10 AM departures from ALO to ORD are the most sought after. Greater demand means you’ll likely pay more for these departures. If you’re hoping to save money, book during off-peak hours.
What day of the week has the most flights from ALO to ORD?
If you jet off on a Friday, you’ll get the largest range of choices for flights from Waterloo Regional Airport (ALO) to O’Hare Intl. Airport (ORD).
What is the earliest flight from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
Waterloo Regional Airport (ALO)’s earliest flight to O’Hare Intl. Airport (ORD) departs at approximately 10:15AM UTC-6. With a travel duration of 1h 22m, you’ll arrive at around 11:37AM UTC-6.
How long does it take to fly from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
The average flight duration from ALO to ORD is 1 hour and 23 minutes, covering a total distance of 230 mi.
What airline has the least delays from ALO to ORD?
American Airlines has the strongest track record for on-time direct flights from Waterloo Regional Airport (ALO) to O’Hare Intl. Airport (ORD), with an on-time score of 84%. Use the Expedia App to see your flight status before you go and get notified of any changes.
What is the best time to fly from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
To avoid potential delays on the Waterloo Regional Airport (ALO) to O’Hare Intl. Airport (ORD) route, travel before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
What airports do you fly into for Chicago from Waterloo Regional Airport (ALO)?
O’Hare Intl. Airport (ORD) is the only airport in Chicago with direct flights from Waterloo Regional Airport (ALO). Check out the options and discover affordable fares on Expedia.
Is it cheaper to buy a plane ticket from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD) last-minute?
Booking your plane ticket from ALO to ORD right before your trip is generally more expensive. However, if there’s some wiggle room with your departure times and dates, you could snag a cheap last-minute fare.
Is it cheaper to book an ALO to ORD flight and hotel package?
Securing an ALO to ORD flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your trip in one place. Select from our extensive range of hotels and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)?
Typically, you’re able to cancel or reschedule your ALO to ORD flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline’s fees and policies on flight changes, or if you’d like more information, go to our Customer Service portal.

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*Available to One Key members.