HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
ALO — CHI
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Waterloo to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$380
(American Airlines)

One-way from

$350
(American Airlines)

Good round-trip deal

$353 or less

Good one-way deal

$240 or less
Provider with most accurate pricing for Waterloo-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Waterloo-Chicago (CHI) flights.
Search Deals
From Waterloo to Chicago (CHI)
Search Deals
One-way flight from Waterloo to Chicago (CHI)
Search Deals
Price to beat on a round-trip flight from Waterloo to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Waterloo to Chicago (CHI).
Search Deals

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 September 29, 2025.

This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 10/253:25 pmALO - ORD
Nonstop1h 30mAmerican Airlines
Sat 11/18:30 pmORD - ALO
Nonstop1h 27mAmerican Airlines
Deal found 9/27$380
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/235:50 amALO - ORD
Nonstop1h 34mAmerican Airlines
Wed 1/141:15 pmORD - ALO
Nonstop1h 05mAmerican Airlines
Deal found 9/27$409
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Sat 10/113:25 pmALO - ORD
Nonstop1h 30mAmerican Airlines
Tue 10/141:44 pmORD - ALO
Nonstop1h 11mAmerican Airlines
Deal found 9/28$423
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/235:50 amALO - ORD
Nonstop1h 34mAmerican Airlines
Sun 1/111:15 pmORD - ALO
Nonstop1h 05mAmerican Airlines
Deal found 9/27$428
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/235:50 amALO - ORD
Nonstop1h 34mAmerican Airlines
Sat 1/101:15 pmORD - ALO
Nonstop1h 05mAmerican Airlines
Deal found 9/27$433
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sun 12/213:12 pmALO - ORD
Nonstop1h 27mAmerican Airlines
Tue 1/138:40 pmORD - ALO
Nonstop1h 21mAmerican Airlines
Deal found 9/27$450
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/223:12 pmALO - ORD
Nonstop1h 27mAmerican Airlines
Mon 1/121:15 pmORD - ALO
Nonstop1h 05mAmerican Airlines
Deal found 9/27$453
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/223:12 pmALO - ORD
Nonstop1h 27mAmerican Airlines
Sat 1/108:40 pmORD - ALO
Nonstop1h 21mAmerican Airlines
Deal found 9/27$455
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Sat 12/273:09 pmALO - ORD
Nonstop1h 27mAmerican Airlines
Tue 1/131:15 pmORD - ALO
Nonstop1h 05mAmerican Airlines
Deal found 9/27$458
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Sun 10/266:00 amALO - ORD
Nonstop1h 26mAmerican Airlines
Sun 11/210:31 pmORD - ALO
Nonstop1h 17mAmerican Airlines
Deal found 9/28$470
This American Airlines deal was found by Cheapflights users on 9/28. 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 9/306:00 amALO - ORD
Nonstop1h 24mAmerican Airlines
Wed 10/13:15 pmORD - ALO
Nonstop1h 14mAmerican Airlines
Deal found 9/28$471
This American Airlines deal was found by Cheapflights users on 9/27. 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 12/265:40 amALO - ORD
Nonstop1h 34mAmerican Airlines
Tue 1/138:40 pmORD - ALO
Nonstop1h 21mAmerican Airlines
Deal found 9/27$472

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 September 29, 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

Tue 12/23

5:50 am-7:24 am

Nonstop1h 34m

Chicago O'Hare Intl

Wed 1/14

1:15 pm-2:20 pm

Nonstop1h 05m

$409

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 12/24

5:40 am-7:14 am

Nonstop1h 34m

Chicago O'Hare Intl

Tue 1/13

8:40 pm-10:01 pm

Nonstop1h 21m

$409

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Thu 12/25

5:40 am-7:14 am

Nonstop1h 34m

Chicago O'Hare Intl

Wed 1/14

1:15 pm-2:20 pm

Nonstop1h 05m

$409

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Sat 10/11

3:25 pm-4:55 pm

Nonstop1h 30m

Chicago O'Hare Intl

Tue 10/14

1:44 pm-2:55 pm

Nonstop1h 11m

$423

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 10/14

6:00 am-7:26 am

Nonstop1h 26m

Chicago O'Hare Intl

Sat 10/18

10:19 pm-11:38 pm

Nonstop1h 19m

$423

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Mon 12/22

5:50 am-7:24 am

Nonstop1h 34m

Chicago O'Hare Intl

Wed 1/14

1:15 pm-2:20 pm

Nonstop1h 05m

$428

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 12/24

5:40 am-7:14 am

Nonstop1h 34m

Chicago O'Hare Intl

Thu 1/15

8:40 pm-10:01 pm

Nonstop1h 21m

$428

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 12/24

5:40 am-7:14 am

Nonstop1h 34m

Chicago O'Hare Intl

Sun 1/11

1:15 pm-2:20 pm

Nonstop1h 05m

$428

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 12/23

5:50 am-7:24 am

Nonstop1h 34m

Chicago O'Hare Intl

Fri 1/16

8:40 pm-10:01 pm

Nonstop1h 21m

$428

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 12/23

5:50 am-7:24 am

Nonstop1h 34m

Chicago O'Hare Intl

Sun 1/11

1:15 pm-2:20 pm

Nonstop1h 05m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/26

Showing 1-10 of 19 results
1
2

Compare providers for flights from Waterloo to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Waterloo to Chicago in September.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Waterloo, Iowa-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Waterloo, Iowa-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Waterloo, Iowa-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Waterloo, Iowa-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Waterloo, Iowa-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 September 29, 2025.

It’s optimal to fly from Waterloo, Iowa to Chicago in the afternoon. By choosing this option you can save up to 15% on the cost of your flight, compared to a flight at noon.

Weekly flight availability from Waterloo, Iowa to Chicago

Explore weekly flight availability from Waterloo to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 29, 2025.

The most flights from ALO to CHI are scheduled on a Monday (3 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (1 on average).

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.

  • How long is the flight from Waterloo, Iowa to Chicago?

    For as low as $409, American Airlines can have you in Chicago from Waterloo, Iowa in 1h 34m. Waterloo, Iowa and Chicago are separated by a distance of 233 mi. All flights are typically nonstop.

  • 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: Qatar Airways (69%), American Airlines (62%), Envoy Air( 62%).

  • 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 $426, our data indicates the cheapest price to be $240. The most popular route (Waterloo - Chicago O'Hare Intl), is priced around $380.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Waterloo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Des Moines to O'Hare Intl flights
Omaha to O'Hare Intl flights
Omaha to Midway flights
Des Moines to Midway flights
Omaha to St. Louis flights
Cedar Rapids to O'Hare Intl flights
Moline to O'Hare Intl flights
Des Moines to St. Louis flights
Cedar Rapids to Midway flights
Sioux City to O'Hare Intl flights
Mason City to O'Hare Intl flights
Dubuque to O'Hare Intl flights
Des Moines to Rockford flights
Burlington to O'Hare Intl flights
Moline to Midway flights
Omaha to Rockford flights
Omaha to Moline flights
Waterloo to O'Hare Intl flights
La Crosse to O'Hare Intl flights
Omaha to Evansville flights
La Crosse to Peoria flights
Omaha to Bloomington flights
La Crosse to Midway flights
Moline to Peoria flights
La Crosse to St. Louis flights
Waterloo to St. Louis flights

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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$324Average$417FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.