App
Customer Support
USD
Find Bookings
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Cheap flight deals from Chicago to Watertown Starting at $221

Whether you’re going for a one-way or round-trip to Watertown, we’ve got you covered! Check out these different flight options from Chicago below.

  • One way
  • Round-trip
      • MDW19:10
        18h 50m
        2 stops
        ART15:00
        Sat, Feb 15|Chicago - Watertown|Frontier Airlines
        $221$339
        35% OFF
        35% OFF
        $339$221

        Choose Frontier Airlines flights from Chicago to Watertown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sat, Feb 15, arriving at Watertown International Airport. One-way Prices start from $221 including taxes and charges.

      • ORD09:45
        4h 15m
        1 stop
        ART15:00
        Sat, Feb 15|Chicago - Watertown|American Airlines
        $221$339
        35% OFF
        35% OFF
        $339$221

        Choose American Airlines flights from Chicago to Watertown. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sat, Feb 15, arriving at Watertown International Airport. One-way Prices start from $221 including taxes and charges.

      • ORD16:18
        5h 29m
        1 stop
        ART22:47
        Mon, Feb 24|Chicago - Watertown|American Airlines
        $276$339
        19% OFF
        19% OFF
        $339$276

        Choose American Airlines flights from Chicago to Watertown. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Mon, Feb 24, arriving at Watertown International Airport. One-way Prices start from $276 including taxes and charges.

      • ORD16:25
        5h 19m
        1 stop
        ART22:44
        Sat, Mar 15|Chicago - Watertown|American Airlines
        $285
        $285

        Choose American Airlines flights from Chicago to Watertown. The one-way connecting flight with American Airlines departs from O'Hare International Airport on Sat, Mar 15, arriving at Watertown International Airport. One-way Prices start from $285 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        ART02:00 pm
        Fri, Feb 21|Chicago - Watertown|Frontier Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Chicago to Watertown flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. AA3703

    American Airlines

    07:00

    ORD

    2.5h

    10:27

    BOS

    SMTWTFS
    Search

  2. AA4348

    American Airlines

    11:05

    BOS

    1.5h

    12:35

    PHL

    SMTWTFS

  3. AA5974

    American Airlines

    11:19

    PHL

    1.5h

    12:50

    ART

    SMTWTFS

  4. AA1784

    American Airlines

    07:00

    ORD

    2.1h

    10:06

    CLT

    SMTWTFS
    Search

  5. AA1687

    American Airlines

    11:15

    CLT

    1.7h

    12:55

    PHL

    SMTWTFS

  6. AA5974

    American Airlines

    11:19

    PHL

    1.5h

    12:50

    ART

    SMTWTFS

  7. UA2418

    United Airlines

    07:30

    ORD

    2.1h

    10:38

    PHL

    SMTWTFS
    Search

  8. AA5974

    American Airlines

    11:19

    PHL

    1.5h

    12:50

    ART

    SMTWTFS

  9. AA1064

    American Airlines

    08:05

    ORD

    2.2h

    11:19

    BOS

    SMTWTFS
    Search

  10. AA1408

    American Airlines

    18:00

    BOS

    1.7h

    19:40

    PHL

    SMTWTFS

  11. AA5700

    American Airlines

    21:25

    PHL

    1.5h

    22:55

    ART

    SMTWTFS

  12. AA6073

    American Airlines

    08:20

    ORD

    1.4h

    10:44

    CLE

    SMTWTFS
    Search

  13. AA5997

    American Airlines

    16:10

    CLE

    1.4h

    17:34

    PHL

    SMTWTFS

  14. AA5700

    American Airlines

    21:25

    PHL

    1.5h

    22:55

    ART

    SMTWTFS

  15. AA2098

    American Airlines

    09:45

    ORD

    2.0h

    12:43

    PHL

    SMTWTFS
    Search

  16. AA5974

    American Airlines

    11:19

    PHL

    1.5h

    12:50

    ART

    SMTWTFS

  17. F91596

    Frontier Airlines

    11:10

    ORD

    2.2h

    14:23

    ATL

    S-T-TFS
    Search

  18. F92298

    Frontier Airlines

    17:15

    ATL

    2.3h

    19:31

    PHL

    S-TWTFS

  19. AA5700

    American Airlines

    21:25

    PHL

    1.5h

    22:55

    ART

    SMTWTFS

  20. AA4394

    American Airlines

    11:50

    ORD

    2.5h

    15:22

    BOS

    -----F-
    Search

  21. AA1408

    American Airlines

    18:00

    BOS

    1.7h

    19:40

    PHL

    SMTWTFS

  22. AA5700

    American Airlines

    21:25

    PHL

    1.5h

    22:55

    ART

    SMTWTFS

  23. AA1570

    American Airlines

    16:18

    ORD

    2.0h

    19:17

    PHL

    S--WT-S
    Search

  24. AA5700

    American Airlines

    21:25

    PHL

    1.5h

    22:55

    ART

    SMTWTFS

  25. AA1941

    American Airlines

    17:18

    ORD

    1.9h

    20:14

    PHL

    SMTWTFS
    Search

  26. AA5700

    American Airlines

    21:25

    PHL

    1.5h

    22:55

    ART

    SMTWTFS
Find more flights and airlines

When is the cheapest time to fly from Chicago to Watertown?

These price trend charts carefully monitor and predict how flight prices from Chicago to Watertown will change. Keep a close eye on them to understand when the best time to buy your tickets is.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Watertown (ART) the cheapest?

    Airlines adjust prices for flights from Chicago to Watertown based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Watertown (ART) cost?

    According to Trip.com's data, the lowest price is around $346.

  • How many airports are there in Watertown (ART)?

    There are 1 airport(s) near Watertown (ART): Watertown International Airport.

How to find a cheap flight from Chicago to Watertown

Understanding the common pitfalls when booking your flight tickets can help you save massively when it comes time to fly. We’ve listed our six essential steps to keep in mind when you’re booking flight tickets to help you find the best price.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Chicago to Watertown

Cheapest direct flight price$221
Off-season for travelJanuary
Peak season for travelDecember
Flight distance973.77 km
Popular airlineAmerican Airlines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.