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Anguilla

$598+ Cheap flights from Illinois to Anguilla

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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Illinois to Anguilla

Cheapest flights from Illinois to Anguilla
Explore the most affordable flight options available from Illinois to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/105:00 amORD - AXA
1 stop7h 23mAmerican Airlines
Sun 12/145:20 pmAXA - ORD
1 stop19h 47mAmerican Airlines
Deal found 11/1$685
This Mytrip deal was found by Cheapflights users on 11/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:00 amORD - AXA
2 stops10h 10mMultiple Airlines
Sun 12/149:00 amAXA - ORD
3 stops40h 59mMultiple Airlines
Deal found 11/1$1,246
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/257:17 pmORD - AXA
1 stop17h 14mAmerican Airlines
Sat 11/292:56 pmAXA - ORD
1 stop10h 03mAmerican Airlines
Deal found 11/2$1,730
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 11/224:40 pmORD - AXA
1 stop22h 21mAmerican Airlines
Sat 11/292:56 pmAXA - ORD
1 stop11h 41mAmerican Airlines
Deal found 11/2$2,022

Cheap flight deals from Illinois to Anguilla

Keep the following information in mind while searching for Illinois to Anguilla flight deals. Data was last updated November 3, 2025.

Round-trip from

$598
(American Airlines)

Popular in

August

Cheapest in

June

Average price

$1,133
From Illinois to Anguilla
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($312 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($98 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois to Anguilla 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 November 3, 2025.
Use the filters below to find and compare flights from Illinois to Anguilla that are best for you.

Fly from

Illinois

Fly to

Anguilla

Route

Depart

Return

Price

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 1/27

7:00 am-4:26 pm

1 stop7h 26m

The Valley Wallblake Intl

Mon 2/2

5:06 pm-12:30 am

1 stop9h 24m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/4

7:00 am-4:26 pm

1 stop7h 26m

The Valley Wallblake Intl

Sun 2/8

5:06 pm-9:05 am

1 stop17h 59m

$603

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/11

3:55 pm-4:46 pm

1 stop22h 51m

The Valley Wallblake Intl

Wed 2/18

5:26 pm-12:36 am

1 stop9h 10m

$613

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/25

5:45 am-4:46 pm

1 stop9h 01m

The Valley Wallblake Intl

Sun 3/1

5:26 pm-9:02 am

1 stop17h 36m

$633

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/11

7:00 am-4:26 pm

1 stop7h 26m

The Valley Wallblake Intl

Sun 2/15

5:26 pm-12:36 am

1 stop9h 10m

$663

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 12/10

5:00 am-2:23 pm

1 stop7h 23m

The Valley Wallblake Intl

Sun 12/14

5:20 pm-11:07 am

1 stop19h 47m

$685

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Best time to book a flight from Illinois to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from Illinois 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 Illinois to Anguilla
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Illinois to Anguilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Illinois to Anguilla?

    American Airlines can get you from Illinois to Anguilla in just under 7h 26m. Your travel time can differ by up to . Illinois and Anguilla are separated by a distance of 2197 mi.

  • Can I find deals for flights from Illinois to Anguilla that include hotel bookings?

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

  • How can I find direct flights from Illinois to Anguilla?

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

  • Can I find deals for business class flights from Illinois to Anguilla?

    Yes. Cheapflights offers flight deals from Illinois to Anguilla by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Illinois to Anguilla

Discover the top airline that operate flights from Illinois to Anguilla. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$602Average$786FlexibilityNo cancel feeOn-time71%

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