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$341+ Cheap flights from Watertown, NY (ART) 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
ART — CHI
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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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 (ART) 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 18, 2025.

Round-trip from

$341
(American Airlines)
From Watertown to Chicago (CHI)
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Cheapest flights from Watertown to Chicago
Explore the most affordable flight options available from Watertown to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/15. 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 7/16:00 amART - ORD
2 stops8h 45mAmerican Airlines
Sat 7/55:05 pmORD - ART
1 stop4h 51mAmerican Airlines
Deal found 6/15$341

Cheapflights Fare Finder

Customize your flight search to find flights from Watertown 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 18, 2025.
Use the filters below to find and compare flights from Watertown to Chicago that are best for you.

Fly from

Watertown

Fly to

Chicago

Route

Depart

Return

Price

WatertownChicago

ART - ORD

ARTORD

Watertown

Tue 7/1

6:00 am-1:45 pm

2 stops8h 45m

Chicago O'Hare Intl

Sat 7/5

5:05 pm-10:56 pm

1 stop4h 51m

$341

WatertownChicago

ART - ORD

ARTORD

Watertown

Thu 7/3

3:38 pm-8:09 pm

1 stop5h 31m

$460

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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, New York to Chicago?

Currently, August is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $245). Flying from Watertown, New York 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.

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 18, 2025.
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2024

LAX - ORD

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.5

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Oct 2024

LAX - ORD

The seats are just SO UNCOMFORTABLE it completely ruins the experience, especially on a redeye. I was so exhausted but couldn’t sleep a wink because it was just so incredibly uncomfortable. I don’t know who designs airplane seats, but they’re curved forward, forcing your body into a slouching position. Please. Please please get new seats. Also ones that actually extent to the bulkhead so that when you try to lean against the wall, you don’t just fall through the gap

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?

    Most people fly from Watertown (ART) if they book a flight from Watertown to Chicago. On average, Watertown has 0 outbound flights to Chicago per day from 0 airlines. Watertown is conveniently located just 5.6 mi from Watertown’s city center.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $341.

  • 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, New York to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Watertown, New York to Chicago (average of $245). Flying from Watertown, New York 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 Watertown?

Book flights to Watertown if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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