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$350+ Cheap flights from Waterloo, IA (ALO) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
ALO — CHI
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Waterloo to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Waterloo (ALO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 14, 2025.

Round-trip from

$359
(American Airlines)

One-way from

$350
(American Airlines)

Good round-trip deal

$314 or less

Good one-way deal

$315 or less
From Waterloo to Chicago (CHI)
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One-way flight from Waterloo to Chicago (CHI)
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Price to beat on a round-trip flight from Waterloo to Chicago (CHI).
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Price to beat on a one-way flight from Waterloo to Chicago (CHI).
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Find flight deals from Waterloo to Chicago

Cheapest flights from Waterloo to Chicago
Explore the most affordable flight options available from Waterloo to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/103:21 pmALO - ORD
Nonstop1h 30mAmerican Airlines
Sat 10/181:40 pmORD - ALO
Nonstop1h 11mAmerican Airlines
Deal found 8/12$359
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amALO - ORD
Nonstop1h 26mAmerican Airlines
Sun 11/21:41 pmORD - ALO
Nonstop1h 17mAmerican Airlines
Deal found 8/13$381
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:00 amALO - ORD
Nonstop1h 22mAmerican Airlines
Tue 8/266:09 pmORD - ALO
Nonstop1h 21mAmerican Airlines
Deal found 8/11$423
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/83:38 pmALO - ORD
Nonstop1h 29mAmerican Airlines
Mon 9/151:52 pmORD - ALO
Nonstop1h 16mAmerican Airlines
Deal found 8/12$470
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:00 amALO - ORD
Nonstop1h 22mAmerican Airlines
Mon 8/251:32 pmORD - ALO
Nonstop1h 12mAmerican Airlines
Deal found 8/12$473
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/283:14 pmALO - ORD
Nonstop1h 23mAmerican Airlines
Mon 9/11:32 pmORD - ALO
Nonstop1h 12mAmerican Airlines
Deal found 8/13$499
This American Airlines deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amALO - ORD
Nonstop1h 22mAmerican Airlines
Thu 8/1410:19 pmORD - ALO
Nonstop1h 18mAmerican Airlines
Deal found 8/12$745

Cheapflights Fare Finder

 
Customize your flight search to find flights from Waterloo to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Waterloo to Chicago that are best for you.

Fly from

Waterloo

Fly to

Chicago

Route

Depart

Return

Price

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 10/10

3:21 pm-4:51 pm

Nonstop1h 30m

Chicago O'Hare Intl

Sat 10/18

1:40 pm-2:51 pm

Nonstop1h 11m

$359

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Sat 11/22

3:28 pm-4:58 pm

Nonstop1h 30m

Chicago O'Hare Intl

Sun 11/23

1:41 pm-2:58 pm

Nonstop1h 17m

$359

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 10/31

6:00 am-7:26 am

Nonstop1h 26m

Chicago O'Hare Intl

Sun 11/2

1:41 pm-2:58 pm

Nonstop1h 17m

$381

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Mon 9/8

3:38 pm-5:07 pm

Nonstop1h 29m

Chicago O'Hare Intl

Mon 9/15

1:52 pm-3:08 pm

Nonstop1h 16m

$470

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 8/29

3:14 pm-4:37 pm

Nonstop1h 23m

Chicago O'Hare Intl

Tue 9/2

6:09 pm-7:30 pm

Nonstop1h 21m

$473

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Thu 8/28

6:00 am-7:22 am

Nonstop1h 22m

Chicago O'Hare Intl

Wed 9/10

8:45 pm-10:05 pm

Nonstop1h 20m

$473

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Thu 8/28

3:14 pm-4:37 pm

Nonstop1h 23m

Chicago O'Hare Intl

Mon 9/1

1:32 pm-2:44 pm

Nonstop1h 12m

$499

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Mon 9/1

6:00 am-7:22 am

Nonstop1h 22m

Chicago O'Hare Intl

Tue 9/2

6:09 pm-7:30 pm

Nonstop1h 21m

$745

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 10/14

3:21 pm-4:51 pm

Nonstop1h 30m

$350

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 9/9

6:00 am-7:24 am

Nonstop1h 24m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 15 results
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Best time to book a flight from Waterloo to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Waterloo with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Waterloo to Chicago

What is the cheapest month to book a flight from Waterloo, Iowa to Chicago?

Currently, August is the cheapest month in which you can book a flight from Waterloo, Iowa to Chicago (average of $245). Flying from Waterloo, Iowa to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ALO to CHI?

Find hourly flight availability from Waterloo to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

It’s optimal to fly from Waterloo, Iowa to Chicago in the afternoon. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight at noon.

Related info for your journey

Find useful and relevant information for your journey from Waterloo to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Waterloo to Chicago?

    Most people fly from Waterloo (ALO) if they book a flight from Waterloo to Chicago. On average, Waterloo has 2 outbound flights to Chicago per day from 1 airline. Waterloo is conveniently located just 5.3 mi from Waterloo’s city center.

  • What is the cheapest airline to fly from Waterloo, Iowa to Chicago round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $324.

  • What are the most reliable airlines from Waterloo, Iowa to Chicago?

    Before booking your flight to Chicago from Waterloo, Iowa, check out the most reliable airlines to get you to your destination on time: Envoy Air (67%), American Airlines (67%), Piedmont Airlines( 67%).

  • What are the cheapest flights from Waterloo, Iowa to Chicago?

    Looking for the cheapest flight from Waterloo, Iowa to Chicago? While on average our users pay $391, our data indicates the cheapest price to be $219. The most popular route (Waterloo - Chicago O'Hare Intl), is priced around $359.

  • Can I find deals for flights from Waterloo to Chicago that include hotel bookings?

    Yes. In addition to deals on Waterloo to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Waterloo to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Waterloo to Chicago.

  • Can I find deals for business class flights from Waterloo to Chicago?

    Yes. Cheapflights offers flight deals from Waterloo to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Waterloo, Iowa to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Waterloo, Iowa to Chicago (average of $245). Flying from Waterloo, Iowa to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Waterloo to Chicago

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Top airline flying from Waterloo to Chicago

Discover the top airline that operate flights from Waterloo to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$324Average$374FlexibilityNo cancel feeOn-time71%

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