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$329+ Cheap flights from Waterloo, IA (ALO) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
ALO — CHI
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap 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 January 27, 2026.

This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 4/86:00 am
ALO
-
ORD
Nonstop1h 26m
American Airlines
Wed 4/1512:25 pm
ORD
-
ALO
Nonstop1h 23m
American Airlines
Deal found 1/27$329
This American Airlines deal was found by Cheapflights users on 1/27. 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 2/285:20 am
ALO
-
ORD
Nonstop1h 25m
American Airlines
Sun 3/110:34 pm
ORD
-
ALO
Nonstop1h 19m
American Airlines
Deal found 1/27$366
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/65:20 am
ALO
-
ORD
Nonstop1h 25m
American Airlines
Sat 3/1410:34 pm
ORD
-
ALO
Nonstop1h 19m
American Airlines
Deal found 1/27$383
This American Airlines deal was found by Cheapflights users on 1/24. 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 2/153:15 pm
ALO
-
ORD
Nonstop1h 24m
American Airlines
Sat 2/2810:34 pm
ORD
-
ALO
Nonstop1h 19m
American Airlines
Deal found 1/24$421
This American Airlines deal was found by Cheapflights users on 1/24. 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 3/273:10 pm
ALO
-
ORD
Nonstop1h 24m
American Airlines
Sun 3/291:21 pm
ORD
-
ALO
Nonstop1h 19m
American Airlines
Deal found 1/24$439
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 2/116:00 am
ALO
-
ORD
Nonstop1h 30m
American Airlines
Sun 2/1510:34 pm
ORD
-
ALO
Nonstop1h 19m
American Airlines
Deal found 1/27$440
This American Airlines deal was found by Cheapflights users on 1/26. 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 4/212:20 pm
ALO
-
ORD
Nonstop1h 27m
American Airlines
Fri 4/2412:25 pm
ORD
-
ALO
Nonstop1h 23m
American Airlines
Deal found 1/26$763
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/96:00 am
ALO
-
ORD
Nonstop1h 30m
American Airlines
Fri 2/131:26 pm
ORD
-
ALO
Nonstop1h 19m
American Airlines
Deal found 1/25$807

Find 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(American Airlines)

Good round-trip deal

$439 or less

Good one-way deal

$269 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)
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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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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 January 27, 2026.
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

Wed 4/8

6:00 am-7:26 am

Nonstop1h 26m

Chicago O'Hare Intl

Wed 4/15

10:27 pm-11:50 pm

Nonstop1h 23m

$329

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Sat 2/28

5:20 am-6:45 am

Nonstop1h 25m

Chicago O'Hare Intl

Sun 3/1

10:34 pm-11:53 pm

Nonstop1h 19m

$366

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 3/6

5:20 am-6:45 am

Nonstop1h 25m

Chicago O'Hare Intl

Sat 3/14

10:34 pm-11:53 pm

Nonstop1h 19m

$383

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Sun 2/15

3:15 pm-4:39 pm

Nonstop1h 24m

Chicago O'Hare Intl

Sat 2/28

10:34 pm-11:53 pm

Nonstop1h 19m

$421

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 2/11

6:00 am-7:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Sun 2/15

10:34 pm-11:53 pm

Nonstop1h 19m

$440

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 4/21

2:20 pm-3:47 pm

Nonstop1h 27m

Chicago O'Hare Intl

Fri 4/24

12:25 pm-1:48 pm

Nonstop1h 23m

$763

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Mon 2/9

6:00 am-7:30 am

Nonstop1h 30m

Chicago O'Hare Intl

Fri 2/13

1:26 pm-2:45 pm

Nonstop1h 19m

$807

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Sat 7/25

5:00 am-6:28 am

Nonstop1h 28m

$360

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 2/25

5:20 am-6:45 am

Nonstop1h 25m

$360

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 7/21

5:00 am-6:28 am

Nonstop1h 28m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Showing 1-10 of 14 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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, February is the cheapest month in which you can book a flight from Waterloo, Iowa to Chicago (average of $148). Flying from Waterloo, Iowa to Chicago in March is currently the most expensive (average of $189). 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 January 27, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Waterloo, Iowa to Chicago as you normally would.

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 1 outbound flight 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 $329, American Airlines can have you in Chicago from Waterloo, Iowa in 1h 26m. Waterloo, Iowa and Chicago are separated by a distance of 233 mi. All flights are typically nonstop.

  • 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: American Airlines (65%), Envoy Air (65%), Qatar Airways( 57%).

  • 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 $445, our data indicates the cheapest price to be $250. The most popular route (Waterloo - Chicago O'Hare Intl), is priced around $329.

  • 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, February is the cheapest month in which you can book a flight from Waterloo, Iowa to Chicago (average of $148). Flying from Waterloo, Iowa to Chicago in March is currently the most expensive (average of $189). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Waterloo to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$236Average$457FlexibilityNo cancel feeOn-time71%

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