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Cheap flights from Chicago to Anguilla from $375

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Anguilla departing on 3/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 pm - 1:14 pm
ORD
-
AXA
18h 14m
1 stop
American Airlines Logo
4:55 pm - 9:10 am
AXA
-
ORD
17h 15m
1 stop
$699American Airlines
Mon, Jun 15 - Mon, Jun 22
American Airlines Logo
8:57 pm - 1:14 pm
ORD
-
AXA
15h 17m
2 stops
American Airlines Logo
4:55 pm - 9:10 am
AXA
-
ORD
17h 15m
1 stop
$704American Airlines
Mon, Jun 15 - Mon, Jun 22
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
AXA
15h 29m
2 stops
American Airlines Logo
4:57 pm - 7:39 am
AXA
-
ORD
15h 42m
2 stops
$734American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
1 stop
American Airlines Logo
4:57 pm - 12:25 am
AXA
-
ORD
8h 28m
1 stop
$744American Airlines
Sat, May 9 - Fri, May 15
American Airlines Logo
5:20 pm - 4:17 pm
ORD
-
AXA
21h 57m
1 stop
American Airlines Logo
4:57 pm - 12:25 am
AXA
-
ORD
8h 28m
1 stop
$747American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
4:05 pm - 1:14 pm
ORD
-
AXA
20h 09m
1 stop
American Airlines Logo
4:55 pm - 9:10 am
AXA
-
ORD
17h 15m
1 stop
$751American Airlines
Thu, Jun 25 - Mon, Jun 29
American Airlines Logo
2:24 pm - 1:14 pm
ORD
-
AXA
21h 50m
1 stop
American Airlines Logo
4:55 pm - 7:32 am
AXA
-
ORD
15h 37m
2 stops
$755American Airlines
Thu, Jun 25 - Mon, Jun 29
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
4:57 pm - 12:25 am
AXA
-
ORD
8h 28m
1 stop
$759American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
4:57 pm - 8:30 am
AXA
-
ORD
16h 33m
2 stops
$764American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
8:40 pm - 4:17 pm
ORD
-
AXA
18h 37m
2 stops
American Airlines Logo
4:57 pm - 12:18 pm
AXA
-
ORD
20h 21m
2 stops
$768American Airlines
Sat, May 9 - Fri, May 15

American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets
American Airlines
Jun 15
ORD6:00 pmChicago O'Hare Intl
18h 14m
1 stop
AXA1:14 pmThe Valley Wallblake Intl
Jun 22
AXA4:55 pmThe Valley Wallblake Intl
17h 15m
1 stop
ORD9:10 amChicago O'Hare Intl
$699
American Airlines
Jun 15
ORD8:57 pmChicago O'Hare Intl
15h 17m
2 stops
AXA1:14 pmThe Valley Wallblake Intl
Jun 22
AXA4:55 pmThe Valley Wallblake Intl
17h 15m
1 stop
ORD9:10 amChicago O'Hare Intl
$704
American Airlines
Apr 30
ORD8:46 pmChicago O'Hare Intl
15h 29m
2 stops
AXA1:15 pmThe Valley Wallblake Intl
May 7
AXA4:57 pmThe Valley Wallblake Intl
15h 42m
2 stops
ORD7:39 amChicago O'Hare Intl
$734

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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, momondo users made 832,500 searches. Data last updated March 17, 2026.
Use the filters below to find and compare flights from Chicago to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 6/15

6:00 pm-1:14 pm

1 stop18h 14m

The Valley Wallblake Intl

Mon 6/22

4:55 pm-9:10 am

1 stop17h 15m

$699

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 6/15

8:57 pm-1:14 pm

2 stops15h 17m

The Valley Wallblake Intl

Mon 6/22

4:55 pm-9:10 am

1 stop17h 15m

$704

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 4/30

8:46 pm-1:15 pm

2 stops15h 29m

The Valley Wallblake Intl

Thu 5/7

4:57 pm-7:39 am

2 stops15h 42m

$734
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 5/9

5:00 am-4:17 pm

1 stop10h 17m

The Valley Wallblake Intl

Fri 5/15

4:57 pm-12:25 am

1 stop8h 28m

$744

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 4/30

5:20 pm-4:17 pm

1 stop21h 57m

The Valley Wallblake Intl

Thu 5/7

4:57 pm-12:25 am

1 stop8h 28m

$747

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 6/25

4:05 pm-1:14 pm

1 stop20h 09m

The Valley Wallblake Intl

Mon 6/29

4:55 pm-9:10 am

1 stop17h 15m

$751

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 6/25

2:24 pm-1:14 pm

1 stop21h 50m

The Valley Wallblake Intl

Mon 6/29

4:55 pm-7:32 am

2 stops15h 37m

$755

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/11

7:00 pm-1:15 pm

1 stop17h 15m

The Valley Wallblake Intl

Sat 4/18

4:57 pm-12:25 am

1 stop8h 28m

$759

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/11

7:00 pm-1:15 pm

1 stop17h 15m

The Valley Wallblake Intl

Sat 4/18

4:57 pm-8:30 am

2 stops16h 33m

$764

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 5/9

8:40 pm-4:17 pm

2 stops18h 37m

The Valley Wallblake Intl

Fri 5/15

4:57 pm-12:18 pm

2 stops20h 21m

$768

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Anguilla from

How to get the cheapest flight ticket from Chicago to Anguilla

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago to Anguilla?

American Airlines is the most popular carrier operating from Chicago to Anguilla

Cheap Chicago to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Anguilla

Fastest flight time

11h 45m

Direct flights

None
The fastest flight from Chicago to Anguilla takes 11h 45m
There are no direct flights from Chicago to Anguilla. There are no popular flight routes from Chicago to Anguilla.
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  • When did momondo last update prices for flights from Chicago to Anguilla?

    Prices for flights from Chicago to Anguilla are updated daily.

  • How many operators does momondo search for flights from Chicago to Anguilla?

  • How old do you have to be to fly from Chicago to Anguilla?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Anguilla.

  • What documentation or ID do you need to fly to Anguilla?

    The travel and health documents required for your trip to Anguilla can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Anguilla. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago to Anguilla

Compare and see reviews for airlines that fly from Chicago to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $529Free CancellationRating
7.1
11,468 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Anguilla?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Anguilla. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Anguilla with flexible booking policies on momondo?

Yes. All flights to Anguilla from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Anguilla?

momondo provides multiple filters to help you find the best flight to Anguilla from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Anguilla right now. Can momondo alert me if prices change?

Price alerts on flights to Anguilla from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $540