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Cheap flights from Watertown (ATY) to Chicago (CHI)

ATY — CHI
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
1 adult, Economy
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1. Tell us where you want to go

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Cheap flight deals from Watertown to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Watertown (ATY) 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 October 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

August

Cheapest in

January

Average price

$169
Provider with most accurate pricing for Watertown-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Watertown-Chicago (CHI) flights.
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 18% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Compare providers for flights from Watertown 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 Watertown to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust 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 Watertown-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Watertown-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Watertown-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Watertown-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 Watertown-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 Watertown to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Watertown 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 Watertown to Chicago

What is the cheapest month to book a flight from Watertown to Chicago?

Currently, March is the cheapest month in which you can book a flight from Watertown to Chicago (average of $187). Flying from Watertown to Chicago in June is currently the most expensive (average of $224). 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.

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 October 8, 2025.
Peruse reviews from past customers who have flown with Denver Air Connection from Watertown to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Denver Air Connection
9.1
Wonderful

Crew

9.5

Overall

9.1

Entertainment

8.2

Food

8.5

Boarding

9.1

Comfort

9.1
Denver Air Connection
9.1
Wonderful
Denver Air Connection
9.1
Wonderful

Crew

9.5

Overall

9.1

Entertainment

8.2

Food

8.5

Boarding

9.1

Comfort

9.1

Related info for your journey

Find useful and relevant information for your journey from Watertown 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 Watertown to Chicago?

    If you book a flight to Chicago from Watertown, you will be flying from Watertown, which is the city’s only airport. Watertown (ATY) is located 2.2 mi from the center of Watertown. There are 0 flights from Watertown to Chicago per day from 1 airline.

  • What is the cheapest airline to fly from Watertown to Chicago round-trip?

    According to our current data, Denver Air Connection ($172), offers the cheapest pricing from Watertown to Chicago. This flight start at 27% lower than the current average price 3 months from now.

  • Can I find deals for flights from Watertown to Chicago that include hotel bookings?

    Yes. In addition to deals on Watertown to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Watertown to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Watertown to Chicago.

  • Can I find deals for business class flights from Watertown to Chicago?

    Yes. Cheapflights offers flight deals from Watertown 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 Watertown to Chicago?

    Currently, March is the cheapest month in which you can book a flight from Watertown to Chicago (average of $187). Flying from Watertown to Chicago in June is currently the most expensive (average of $224). 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
Porter
Benton Harbor
Chesterton

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Top airline flying from Watertown to Chicago

Discover the top airline that operate flights from Watertown 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 October 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
Denver Air ConnectionCheapest$172Average$194FlexibilityNo cancel feeOn-timeN/A

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