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$337+ 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
ALO — CHI
Mar 9 — Mar 161
Sun 3/9
Sun 3/16
1 adult, Economy
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1. Tell us where you want to go
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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 March 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(American Airlines)

One-way from

$350
(American Airlines)

Good round-trip deal

$339 or less

Good one-way deal

$357 or less
Provider with most accurate pricing for Waterloo-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Waterloo-Chicago (CHI) flights.
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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 March 4, 2025.

This American Airlines deal was found by Cheapflights users on 3/2. 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 6/42:57 pmALO - ORD
Nonstop1h 22mAmerican Airlines
Sat 6/2810:10 pmORD - ALO
Nonstop1h 19mAmerican Airlines
Deal found 3/2$337

Find flights from Waterloo to Chicago within your budget

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 March 4, 2025.

Fly from

Waterloo

Fly to

Chicago

Route

Depart

Return

Price

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Fri 4/4

2:54 pm-4:19 pm

Nonstop1h 25m

Chicago O'Hare Intl

Tue 4/8

8:40 pm-10:02 pm

Nonstop1h 22m

$354

WaterlooChicago

ALO - ORD

ALOORD

Waterloo

Tue 4/1

9:53 am-11:10 am

Nonstop1h 17m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/3

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 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.

Travel insights for flights from Waterloo to Chicago

Get recent, data-driven insights about flights from Waterloo to Chicago including ideal travel times, pricing trends, and more.

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 $326). 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 March 4, 2025.

It’s optimal to fly from Waterloo, Iowa to Chicago in the morning. By choosing this option you can save up to 9% on the cost of your flight, compared to a flight at noon.

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 March 4, 2025.
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Overall

7.2

Comfort

7.3

Food

6.5

Entertainment

7.0

Boarding

7.5

Reviews

1 / 20

10.0
Excellent

Anonymous,Jan 2025

PIT - DFW

Due to gate changes,we nearly missed our flight. The gate agent reassigned our seats and would NOT give us our assigned seats,but she did honor that same request to the man who arrived after us. Her rudeness and difficulty was not appropriate.

American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Overall

7.2

Comfort

7.3

Food

6.5

Entertainment

7.0

Boarding

7.5

Reviews

1 / 20

10.0
Excellent

Anonymous,Jan 2025

PIT - DFW

Due to gate changes,we nearly missed our flight. The gate agent reassigned our seats and would NOT give us our assigned seats,but she did honor that same request to the man who arrived after us. Her rudeness and difficulty was not appropriate.

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 0 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 $354.

  • 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 (86%), Air Wisconsin (86%), Qatar Airways( 76%).

  • 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 $397, our data indicates the cheapest price to be $209. The most popular route (Waterloo - Chicago O'Hare Intl), is priced around $337.

  • 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 $326). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 March 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$324Average$383FlexibilityNo cancel feeOn-time71%
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