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Cheap flight deals from Chicago to Jamestown Starting at AED 1,080

Discover our range of affordable one-way and round-trip flights from Chicago to Jamestown and kick-start your next adventure today!

  • Round-trip
      • ORD05:00
        7h 44m
        1 stop
        JMS12:44
        Thu, Mar 13|Chicago - Jamestown|United Airlines
        JMS13:20
        5h 35m
        1 stop
        ORD18:55
        Wed, Mar 19|Jamestown - Chicago|United Airlines
        AED 1,080AED 1,756
        39% OFF
        39% OFF
        AED 1,756AED 1,080

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Thu, Mar 13-Wed, Mar 19, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,080 including taxes and charges.

      • ORD05:00
        7h 44m
        1 stop
        JMS12:44
        Fri, Mar 14|Chicago - Jamestown|United Airlines
        JMS16:55
        7h 28m
        1 stop
        ORD00:23
        Thu, Mar 20|Jamestown - Chicago|United Airlines
        AED 1,084AED 1,756
        38% OFF
        38% OFF
        AED 1,756AED 1,084

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Mar 14-Thu, Mar 20, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,084 including taxes and charges.

      • ORD05:00
        7h 44m
        1 stop
        JMS12:44
        Fri, Mar 7|Chicago - Jamestown|United Airlines
        JMS16:55
        7h 28m
        1 stop
        ORD00:23
        Mon, Mar 10|Jamestown - Chicago|United Airlines
        AED 1,090AED 1,756
        38% OFF
        38% OFF
        AED 1,756AED 1,090

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Fri, Mar 7-Mon, Mar 10, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,090 including taxes and charges.

      • ORD08:45
        7h 41m
        1 stop
        JMS16:26
        Wed, Feb 19|Chicago - Jamestown|United Airlines
        JMS16:55
        7h 3m
        1 stop
        ORD23:58
        Tue, Feb 25|Jamestown - Chicago|United Airlines
        AED 1,213
        AED 1,213

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Wed, Feb 19-Tue, Feb 25, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,213 including taxes and charges.

      • MDW06:40
        30h 4m
        1 stop
        JMS12:44
        Thu, Mar 13|Chicago - Jamestown|Frontier Airlines
        JMS13:20
        10h 57m
        1 stop
        MDW00:17
        Wed, Mar 19|Jamestown - Chicago|United Airlines
        AED 1,235
        AED 1,235

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Thu, Mar 13-Wed, Mar 19, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,235 including taxes and charges.

      • MDW06:40
        9h 39m
        1 stop
        JMS16:19
        Tue, Mar 11|Chicago - Jamestown|Frontier Airlines
        JMS13:20
        11h 24m
        1 stop
        ORD00:44
        Mon, Mar 17|Jamestown - Chicago|United Airlines
        AED 1,239
        AED 1,239

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Mar 11-Mon, Mar 17, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,239 including taxes and charges.

      • ORD08:45
        7h 34m
        1 stop
        JMS16:19
        Tue, Mar 11|Chicago - Jamestown|United Airlines
        JMS16:55
        7h 28m
        1 stop
        ORD00:23
        Mon, Mar 17|Jamestown - Chicago|United Airlines
        AED 1,316
        AED 1,316

        Choose United Airlines flights from Chicago to Jamestown. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Tue, Mar 11-Mon, Mar 17, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,316 including taxes and charges.

      • MDW07:05
        29h 40m
        1 stop
        JMS12:45
        Tue, Feb 18|Chicago - Jamestown|Frontier Airlines
        JMS13:20
        11h 24m
        1 stop
        ORD00:44
        Mon, Feb 24|Jamestown - Chicago|United Airlines
        AED 1,380
        AED 1,380

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Tue, Feb 18-Mon, Feb 24, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,380 including taxes and charges.

      • MDW06:40
        9h 46m
        1 stop
        JMS16:26
        Thu, Feb 13|Chicago - Jamestown|Frontier Airlines
        JMS13:20
        10h 57m
        1 stop
        MDW00:17
        Sun, Feb 16|Jamestown - Chicago|United Airlines
        AED 1,427
        AED 1,427

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Thu, Feb 13-Sun, Feb 16, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,427 including taxes and charges.

      • MDW06:40
        9h 46m
        1 stop
        JMS16:26
        Sat, Feb 15|Chicago - Jamestown|Frontier Airlines
        JMS13:20
        10h 57m
        1 stop
        MDW00:17
        Fri, Feb 21|Jamestown - Chicago|United Airlines
        AED 1,448
        AED 1,448

        Choose Frontier Airlines flights from Chicago to Jamestown. The one-way connecting flight with Frontier Airlines departs from Midway International Airport on Sat, Feb 15-Fri, Feb 21, arriving at Jamestown Regional Airport. One-way Prices start from AED 1,448 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        JMS02:00 pm
        Thu, Feb 20|Chicago - Jamestown|United 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 Jamestown flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. F93173

    Frontier Airlines

    06:00

    ORD

    3.0h

    07:57

    DEN

    SMTWTFS
    Search

  2. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  3. AA3209

    American Airlines

    06:46

    ORD

    2.5h

    09:19

    DFW

    SMTWTFS
    Search

  4. AA2359

    American Airlines

    10:20

    DFW

    2.4h

    11:45

    DEN

    SMTWTFS

  5. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  6. AA1647

    American Airlines

    06:55

    ORD

    2.7h

    08:36

    DEN

    SMTWT-S
    Search

  7. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  8. F92209

    Frontier Airlines

    07:15

    MDW

    2.8h

    09:05

    DEN

    SMTWTFS
    Search

  9. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  10. UA1599

    United Airlines

    08:45

    ORD

    2.8h

    10:35

    DEN

    SMTWTFS
    Search

  11. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  12. AA1479

    American Airlines

    11:45

    ORD

    2.8h

    13:31

    DEN

    S--WT-S
    Search

  13. UA5102

    United Airlines

    08:15

    DEN

    3.6h

    12:52

    JMS

    S-TWTFS

  14. UA5593

    United Airlines

    17:50

    ORD

    1.4h

    20:15

    DTW

    SMTWTFS
    Search

  15. UA1177

    United Airlines

    08:36

    DTW

    3.5h

    10:05

    DEN

    SMTWTFS

  16. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  17. UA2666

    United Airlines

    20:02

    ORD

    14.6h

    09:37

    DEN

    SMT--FS
    Search

  18. UA5102

    United Airlines

    08:15

    DEN

    3.6h

    12:52

    JMS

    S-TWTFS

  19. UA3650

    United Airlines

    21:17

    ORD

    1.2h

    23:30

    IND

    SMTWTFS
    Search

  20. UA1607

    United Airlines

    08:00

    IND

    3.0h

    08:59

    DEN

    SMTWTFS

  21. UA5053

    United Airlines

    13:35

    DEN

    1.9h

    16:29

    JMS

    SMTWTFS

  22. AA1387

    American Airlines

    21:20

    ORD

    2.8h

    23:08

    DEN

    SMTWTFS
    Search

  23. UA5102

    United Airlines

    08:15

    DEN

    3.6h

    12:52

    JMS

    S-TWTFS
Find more flights and airlines

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

Explore the best time to buy affordable tickets to Jamestown with our price trend chart, which predicts how flight prices will change in the coming weeks from previous data.

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 Jamestown (JMS) the cheapest?

    Airlines adjust prices for flights from Chicago to Jamestown 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 Jamestown (JMS) cost?

    According to Trip.com's data, the lowest price is around AED 1,616.

  • How many airports are there in Jamestown (JMS)?

    There are 1 airport(s) near Jamestown (JMS): Jamestown Regional Airport.

How to find a cheap flight from Chicago to Jamestown

If you don’t know some of the key things to look out for when buying flight tickets, prices can often end up sky high or, worse, sold out! We’ve carefully compiled our six most important steps to help ensure you’re getting the best deals when planning your next journey.
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 Jamestown

Off-season for travelJanuary
Peak season for travelDecember
Flight distance1,040.16 km
Popular airlineAmerican Airlines

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