$159+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
ALO — CHI
Dec 7 — Dec 141
Round-trip
1 adult, Economy
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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
Cheapest
Best
Last-minute
One-way
Cheapest flights from Waterloo to ChicagoExplore 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 November 7, 2026.
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 November 7, 2026.
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/176:04 am -
Nonstop1h 35m
Sat 11/2110:15 pm -
Nonstop1h 26m
Deal found 11/3![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 11/76:04 am -
Nonstop1h 35m
Mon 11/91:47 pm -
Nonstop1h 26m
Deal found 11/2![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 11/7. 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 11/295:56 am -
Nonstop1h 43m
Mon 11/301:45 pm -
Nonstop1h 29m
Deal found 11/7![American Airlines logo]()
$413
Best flights from Waterloo to ChicagoDiscover carefully curated flight deals from Waterloo to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 7, 2026.
Discover carefully curated flight deals from Waterloo to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 7, 2026.
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 12/15:56 am -
Nonstop1h 43m
Tue 12/810:45 pm -
Nonstop1h 29m
Deal found 11/2![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/186:04 am -
Nonstop1h 35m
Sun 11/2210:15 pm -
Nonstop1h 26m
Deal found 11/3![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/225:56 am -
Nonstop1h 43m
Sun 11/221:45 pm -
Nonstop1h 29m
Deal found 11/3![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/6. 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 11/215:56 am -
Nonstop1h 43m
Wed 11/251:45 pm -
Nonstop1h 29m
Deal found 11/6![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/205:56 am -
Nonstop1h 43m
Tue 11/2410:15 pm -
Nonstop1h 26m
Deal found 11/5![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/3. 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 2/223:52 pm -
Nonstop1h 36m
Wed 3/311:01 pm -
Nonstop1h 28m
Deal found 11/3![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 11/3. 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 2/275:25 am -
Nonstop1h 34m
Wed 3/311:01 pm -
Nonstop1h 28m
Deal found 11/3![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 11/3. 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 2/255:25 am -
Nonstop1h 34m
Fri 3/511:01 pm -
Nonstop1h 28m
Deal found 11/3![American Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/253:44 pm -
Nonstop1h 42m
Sun 11/291:45 pm -
Nonstop1h 29m
Deal found 11/5![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 11/7. 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 11/295:56 am -
Nonstop1h 43m
Mon 11/301:45 pm -
Nonstop1h 29m
Deal found 11/7![American Airlines logo]()
$413
Last-minute flights from Waterloo to ChicagoDiscover last-minute flight deals from Waterloo to Chicago. Data last updated November 7, 2026 and is based on user searches.
Discover last-minute flight deals from Waterloo to Chicago. Data last updated November 7, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 11/76:04 am -
Nonstop1h 35m
Mon 11/91:47 pm -
Nonstop1h 26m
Deal found 11/2![American Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 11/3. 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 11/176:04 am -
Nonstop1h 35m
Sat 11/2110:15 pm -
Nonstop1h 26m
Deal found 11/3![American Airlines logo]()
$224
This American Airlines deal was found by Cheapflights users on 11/7. 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 11/295:56 am -
Nonstop1h 43m
Mon 11/301:45 pm -
Nonstop1h 29m
Deal found 11/7![American Airlines logo]()
$413
One-way flights from Waterloo to ChicagoSearch for one-way flight options from Waterloo to Chicago. Find affordable one-way fares based on user searches. Data last updated November 7, 2026.
Search for one-way flight options from Waterloo to Chicago. Find affordable one-way fares based on user searches. Data last updated November 7, 2026.
This American Airlines deal was found by Cheapflights users on 11/6. 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 12/43:44 pm -
Nonstop1h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![American Airlines logo]()
$159
This American Airlines deal was found by Cheapflights users on 11/5. 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 11/215:56 am -
Nonstop1h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![American Airlines logo]()
$209
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 November 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $224 (American Airlines) |
One-way from | $159 (American Airlines) |
Good round-trip deal | $473 or less |
Good one-way deal | $294 or less |
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 7,457,451 searches. Data last updated November 7, 2026.
Use the filters below to find and compare flights from Waterloo to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Mon 12/21
7:04 am-8:45 am
Nonstop1h 41m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Fri 12/4
3:44 pm-5:29 pm
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Wed 12/9
3:44 pm-5:29 pm
Nonstop1h 45m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$159
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Sat 11/21
5:56 am-7:39 am
Nonstop1h 43m
Chicago O'Hare Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$209
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Tue 12/1
5:56 am-7:39 am
Nonstop1h 43m
Chicago O'Hare Intl
Tue 12/8
10:45 pm-12:14 am
Nonstop1h 29m
$224
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Wed 11/18
6:04 am-7:39 am
Nonstop1h 35m
Chicago O'Hare Intl
Sun 11/22
10:15 pm-11:41 pm
Nonstop1h 26m
$224
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Sun 11/22
5:56 am-7:39 am
Nonstop1h 43m
Chicago O'Hare Intl
Sun 11/22
1:45 pm-3:14 pm
Nonstop1h 29m
$224
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Sat 11/21
5:56 am-7:39 am
Nonstop1h 43m
Chicago O'Hare Intl
Wed 11/25
1:45 pm-3:14 pm
Nonstop1h 29m
$224
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Fri 11/20
5:56 am-7:39 am
Nonstop1h 43m
Chicago O'Hare Intl
Tue 11/24
10:15 pm-11:41 pm
Nonstop1h 26m
$224
WaterlooChicago
ALO Waterloo - ORD Chicago O'Hare Intl
ALOORD
Waterloo
Mon 2/22
3:52 pm-5:28 pm
Nonstop1h 36m
Chicago O'Hare Intl
Wed 3/3
11:01 pm-12:29 am
Nonstop1h 28m
$264
Showing 1-10 of 14 resultsSorted by cheapest first
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- 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.
ALO-CHI
ALO-ORD
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
ALO-CHI
ALO-ORD
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 November 7, 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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Merrillville
Lansing
Valparaiso
Hammond
Saint Joseph
Porter
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 7, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
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Waterloo and Chicago flights
Browse other Waterloo and Chicago flight options. Last updated on November 7, 2026.
Other flights from Waterloo
Browse through other flights departing from Waterloo. Flights are based on user searches made on Cheapflights and were last updated on November 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated November 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$203 | Average$303 | FlexibilityNo cancel fee | On-time71% |