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Anguilla

$282+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Mon 12/2912:30 pmAXA - ORD
2 stops29h 12mMultiple Airlines
Deal found 12/16$770
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/208:35 pmORD - AXA
1 stop15h 38mAmerican Airlines
Thu 12/252:53 pmAXA - ORD
1 stop11h 00mAmerican Airlines
Deal found 12/15$824
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Wed 12/3112:30 pmAXA - ORD
2 stops28h 32mMultiple Airlines
Deal found 12/16$826
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Sat 12/2712:30 pmAXA - ORD
2 stops14h 00mMultiple Airlines
Deal found 12/16$860
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/245:00 amORD - AXA
1 stop7h 13mAmerican Airlines
Mon 12/295:30 pmAXA - ORD
1 stop9h 13mAmerican Airlines
Deal found 12/17$943
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:00 amORD - AXA
2 stops10h 10mMultiple Airlines
Mon 12/2912:30 pmAXA - ORD
1 stop12h 55mMultiple Airlines
Deal found 12/16$967
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:26 pmORD - AXA
2 stops23h 44mMultiple Airlines
Mon 12/293:30 pmAXA - ORD
1 stop9h 55mMultiple Airlines
Deal found 12/16$979
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Sun 12/2810:30 amAXA - ORD
2 stops14h 55mMultiple Airlines
Deal found 12/16$993
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:40 amORD - AXA
1 stop31h 10mMultiple Airlines
Thu 1/112:30 pmAXA - ORD
2 stops11h 54mMultiple Airlines
Deal found 12/16$1,013

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 December 18, 2025.

Round-trip from

$529
(American Airlines)

One-way from

$282
(Kiwi.com)
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 December 18, 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

Sat 2/21

7:13 pm-2:19 pm

1 stop17h 06m

The Valley Wallblake Intl

Thu 2/26

5:24 pm-9:02 am

1 stop17h 38m

$529

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 3/6

5:45 am-4:44 pm

1 stop8h 59m

The Valley Wallblake Intl

Mon 3/16

4:18 pm-9:05 am

1 stop17h 47m

$545

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 3/7

7:13 pm-3:38 pm

1 stop18h 25m

The Valley Wallblake Intl

Sat 3/14

4:35 pm-9:05 am

1 stop17h 30m

$567

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 2/18

7:00 am-4:44 pm

1 stop7h 44m

The Valley Wallblake Intl

Sun 2/22

5:24 pm-9:02 am

1 stop17h 38m

$584

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 3/12

6:00 am-3:38 pm

1 stop8h 38m

The Valley Wallblake Intl

Thu 3/19

4:18 pm-12:35 am

1 stop9h 17m

$598

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 2/17

5:00 am-2:19 pm

1 stop7h 19m

The Valley Wallblake Intl

Sat 2/21

5:24 pm-12:33 am

1 stop9h 09m

$689

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 1/17

5:32 pm-1:30 pm

2 stops41h 58m

$282

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 1/27

5:00 am-2:23 pm

1 stop7h 23m

$335

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 1/17

7:30 pm-2:23 pm

1 stop16h 53m

$360

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 1/16

7:30 pm-12:34 pm

1 stop15h 04m

$385

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 11 results
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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 17h 06m. 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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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$597Average$754FlexibilityNo cancel feeOn-time71%

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