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Cheap flight deals from Chicago to Anguilla Starting at AED 2,134

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

  • One way
  • Round-trip
      • ORD08:50
        6h 45m
        1 stop
        AXA17:35
        Wed, Feb 19|Chicago - Anguilla|United Airlines
        AED 2,134AED 3,973
        46% OFF
        46% OFF
        AED 3,973AED 2,134

        Choose United Airlines flights from Chicago to Anguilla. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Wed, Feb 19, arriving at Clayton J. Lloyd International Airport. One-way Prices start from AED 2,134 including taxes and charges.

      • ORD10:45
        28h 50m
        1 stop
        AXA17:35
        Thu, Mar 6|Chicago - Anguilla|United Airlines
        AED 2,423AED 3,973
        39% OFF
        39% OFF
        AED 3,973AED 2,423

        Choose United Airlines flights from Chicago to Anguilla. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Thu, Mar 6, arriving at Clayton J. Lloyd International Airport. One-way Prices start from AED 2,423 including taxes and charges.

      • ORD08:50
        6h 45m
        1 stop
        AXA17:35
        Sat, Feb 22|Chicago - Anguilla|United Airlines
        AED 3,297AED 3,973
        17% OFF
        17% OFF
        AED 3,973AED 3,297

        Choose United Airlines flights from Chicago to Anguilla. The one-way connecting flight with United Airlines departs from O'Hare International Airport on Sat, Feb 22, arriving at Clayton J. Lloyd International Airport. One-way Prices start from AED 3,297 including taxes and charges.

      • CHI01:00 pm
        3h 5m
        Nonstop
        AXA02:00 pm
        Thu, Feb 20|Chicago - Anguilla|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 Anguilla flight time & flight schedules

Flight info.
Departure
Arrival
Weekly Schedule

  1. AA2842

    American Airlines

    05:00

    ORD

    2.1h

    08:07

    CLT

    SMTWTFS
    Search

  2. AA2154

    American Airlines

    08:59

    CLT

    2.2h

    11:13

    MIA

    SMTWTFS

  3. AA3702

    American Airlines

    12:10

    MIA

    3.1h

    15:15

    AXA

    SMTWTFS

  4. AA2984

    American Airlines

    05:00

    ORD

    3.2h

    09:10

    MIA

    SMTWTFS
    Search

  5. AA3419

    American Airlines

    10:05

    MIA

    3.0h

    13:05

    AXA

    SMTWTFS

  6. AA1411

    American Airlines

    07:00

    ORD

    3.2h

    11:10

    MIA

    SMTWTFS
    Search

  7. AA3702

    American Airlines

    12:10

    MIA

    3.1h

    15:15

    AXA

    SMTWTFS

  8. UA2176

    United Airlines

    08:50

    ORD

    4.8h

    15:40

    STT

    --T--FS
    Search

  9. UA6400

    United Airlines

    16:40

    STT

    0.9h

    17:35

    AXA

    SMTWTFS

  10. UA2176

    United Airlines

    08:50

    ORD

    4.8h

    15:40

    STT

    --T--FS
    Search

  11. 9K3951

    Cape Air

    16:40

    STT

    0.9h

    17:35

    AXA

    SMTWTFS

  12. AA3095

    American Airlines

    17:36

    ORD

    1.9h

    20:30

    CLT

    SMTWT-S
    Search

  13. AA3068

    American Airlines

    22:25

    CLT

    2.0h

    00:25

    MIA

    SMTWTFS

  14. AA3419

    American Airlines

    10:05

    MIA

    3.0h

    13:05

    AXA

    SMTWTFS

  15. UA2424

    United Airlines

    18:17

    ORD

    2.1h

    21:26

    RDU

    SMTWTFS
    Search

  16. AA1088

    American Airlines

    06:40

    RDU

    2.4h

    09:01

    MIA

    SMTWTFS

  17. AA3419

    American Airlines

    10:05

    MIA

    3.0h

    13:05

    AXA

    SMTWTFS

  18. AA1359

    American Airlines

    19:03

    ORD

    2.2h

    22:13

    PHL

    SMTWTFS
    Search

  19. AA2738

    American Airlines

    06:05

    PHL

    2.9h

    09:00

    MIA

    SMTWTFS

  20. AA3419

    American Airlines

    10:05

    MIA

    3.0h

    13:05

    AXA

    SMTWTFS

  21. AA2281

    American Airlines

    20:35

    ORD

    2.7h

    23:17

    DFW

    SMTWTFS
    Search

  22. AA3055

    American Airlines

    06:15

    DFW

    2.8h

    10:04

    MIA

    SMTWTFS

  23. AA3419

    American Airlines

    10:05

    MIA

    3.0h

    13:05

    AXA

    SMTWTFS

  24. UA1633

    United Airlines

    21:40

    ORD

    2.1h

    00:45

    EWR

    SMTWTFS
    Search

  25. UA1529

    United Airlines

    11:38

    EWR

    4.1h

    15:43

    STT

    SMTWTFS

  26. UA6400

    United Airlines

    16:40

    STT

    0.9h

    17:35

    AXA

    SMTWTFS
Find more flights and airlines

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

Explore the best time to buy affordable tickets to Anguilla 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 Anguilla (AXA) the cheapest?

    Airlines adjust prices for flights from Chicago to Anguilla 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 Anguilla (AXA) cost?

    According to Trip.com's data, the lowest price is around AED 3,486.

  • How many airports are there in Anguilla (AXA)?

    There are 1 airport(s) near Anguilla (AXA): Clayton J. Lloyd International Airport.

How to find a cheap flight from Chicago to Anguilla

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 Anguilla

Cheapest direct flight priceAED 2,134
Off-season for travelJanuary
Peak season for travelDecember
Flight distance3,513.43 km
Popular airlineAmerican Airlines

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