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$338+ 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 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
ALO — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$338
(American Airlines)

Good round-trip deal

$338 or less

Good one-way deal

$229 or less
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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/263:06 pmALO - ORD
Nonstop1h 22mAmerican Airlines
Sat 8/21:26 pmORD - ALO
Nonstop1h 10mAmerican Airlines
Deal found 6/11$338

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 June 12, 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

Sat 7/26

3:06 pm-4:28 pm

Nonstop1h 22m

Chicago O'Hare Intl

Sat 8/2

1:26 pm-2:36 pm

Nonstop1h 10m

$338

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Wed 7/30

6:00 am-7:18 am

Nonstop1h 18m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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 June 12, 2025.

It’s optimal to fly from Waterloo, Iowa to Chicago in the afternoon. By choosing this option you can save up to 9% 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 June 12, 2025.

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

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated June 12, 2025.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.5

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Andrew,May 2025

LAX - MIA

2 hour delay. Discovered an engine problem late, we boarded the plane and they asked us to come off. To add insult to injury nothing was given to passengers to make amends. No free drink. No extra food or snacks. No free WiFi. Gimme a break

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 3 outbound flights to Chicago per day from 1 airline. Waterloo is conveniently located just 5.3 mi from Waterloo’s city center.

  • 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 (83%), American Airlines (59%), Piedmont Airlines( 59%).

  • 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 $398, our data indicates the cheapest price to be $129. 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 Waterloo?

Book flights to Waterloo if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$324Average$374FlexibilityNo cancel feeOn-time71%

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