$351+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — AXA
Aug 5 — Aug 121
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.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 July 31, 2025.
Round-trip from | $598 (American Airlines) |
|---|---|
One-way from | $351 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $866 |
Find flight deals from Illinois to Anguilla
Cheapest flights from Illinois to AnguillaExplore 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 July 31, 2025.
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 July 31, 2025.
This American Airlines deal was found by Cheapflights users on 7/31. 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 10/115:00 amORD - AXA
1 stop7h 18mAmerican Airlines
Wed 10/152:05 pmAXA - ORD
1 stop9h 26mAmerican Airlines
Deal found 7/31![American Airlines logo]()
$598
This United deal was found by Cheapflights users on 7/30. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:37 pmORD - AXA
2 stops22h 31mMultiple Airlines
Fri 1/29:30 amAXA - ORD
2 stops13h 46mMultiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$2,705
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 July 31, 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 10/11
5:00 am-1:18 pm
1 stop7h 18m
The Valley Wallblake Intl
Wed 10/15
2:05 pm-10:31 pm
1 stop9h 26m
$598
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Fri 12/26
2:37 pm-3:08 pm
2 stops22h 31m
The Valley Wallblake Intl
Fri 1/2
9:30 am-9:16 pm
2 stops13h 46m
$2,705
ChicagoThe Valley
ORD - AXA
ORDAXA
Chicago O'Hare Intl
Tue 9/2
8:12 pm-3:40 pm
2 stops18h 28m
$351
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.
Reviews of airlines servicing Anguilla
Get insights into the airlines that provide service to Anguilla. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Anguilla. Reviews last updated July 31, 2025.
See what other customers who have flown with American Airlines from Illinois to Anguilla have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.5
Entertainment
6.9
Boarding
7.5
Overall
7.2
Crew
8.0
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentLeonardo,May 2025
JFK - BGI
Food
6.5
Entertainment
6.9
Boarding
7.5
Overall
7.2
Crew
8.0
Comfort
7.2
Reviews
1 / 20
10.0
ExcellentLeonardo,May 2025
JFK - BGI
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.
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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.
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 July 31, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$614 | Average$907 | FlexibilityNo cancel fee | On-time71% |