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Anguilla

$345+ Cheap flights from Illinois to Anguilla

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/95:00 am
ORD
-
AXA
1 stop9h 26m
American Airlines
Tue 2/175:10 pm
AXA
-
ORD
1 stop9h 27m
American Airlines
Deal found 1/26$536
This American Airlines deal was found by Cheapflights users on 1/26. 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.
Sun 2/225:00 am
ORD
-
AXA
1 stop7h 30m
American Airlines
Wed 2/255:10 pm
AXA
-
ORD
1 stop17h 43m
American Airlines
Deal found 1/26$578
This American Airlines deal was found by Cheapflights users on 1/28. 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 2/286:59 pm
ORD
-
AXA
1 stop19h 29m
American Airlines
Wed 3/45:10 pm
AXA
-
ORD
1 stop17h 43m
American Airlines
Deal found 1/28$590
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 2/235:00 am
ORD
-
AXA
1 stop9h 28m
American Airlines
Mon 3/25:10 pm
AXA
-
ORD
1 stop9h 27m
American Airlines
Deal found 1/27$603
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/116:58 pm
ORD
-
AXA
1 stop17h 17m
American Airlines
Sat 4/184:57 pm
AXA
-
ORD
1 stop8h 30m
American Airlines
Deal found 1/27$619
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 4/55:00 am
ORD
-
AXA
2 stops9h 29m
American Airlines
Sun 4/124:57 pm
AXA
-
ORD
1 stop8h 30m
American Airlines
Deal found 1/27$629

Find flight deals from Illinois to Anguilla

Keep the following information in mind while searching for Illinois to Anguilla flight deals. Data was last updated January 29, 2026.

Round-trip from

$536
(American Airlines)

One-way from

$345
(American Airlines)
From Illinois to Anguilla
Search Deals
One-way flight from Illinois to Anguilla
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 January 29, 2026.
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

Mon 2/9

5:00 am-4:26 pm

1 stop9h 26m

The Valley Wallblake Intl

Tue 2/17

5:10 pm-12:37 am

1 stop9h 27m

$536

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/23

6:01 am-4:28 pm

1 stop8h 27m

The Valley Wallblake Intl

Fri 2/27

5:10 pm-12:37 am

1 stop9h 27m

$578

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 2/22

10:15 pm-2:30 pm

2 stops14h 15m

The Valley Wallblake Intl

Wed 2/25

5:10 pm-7:25 am

2 stops16h 15m

$583

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 2/28

6:59 pm-4:28 pm

1 stop19h 29m

The Valley Wallblake Intl

Wed 3/4

5:10 pm-8:53 am

1 stop17h 43m

$590

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/23

5:00 am-4:28 pm

1 stop9h 28m

The Valley Wallblake Intl

Mon 3/2

5:10 pm-12:37 am

1 stop9h 27m

$603

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 3/11

5:00 am-3:29 pm

1 stop9h 29m

The Valley Wallblake Intl

Wed 3/18

4:09 pm-12:38 am

1 stop9h 29m

$624

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/11

8:44 pm-1:15 pm

2 stops15h 31m

The Valley Wallblake Intl

Sat 4/18

4:57 pm-7:33 am

2 stops15h 36m

$624

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 4/6

6:00 am-3:29 pm

1 stop8h 29m

$345

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 3/29

6:59 pm-3:29 pm

1 stop19h 30m

$471

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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 9h 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Illinois to Anguilla

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$597Average$731FlexibilityNo cancel feeOn-time71%

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