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Cheap flights from Chicago O'Hare Intl Airport to Anguilla from $380

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 O'Hare Intl Airport to Anguilla departing on 7/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:59 pm - 1:11 pm
ORD
-
AXA
18h 12m
1 stop
American Airlines Logo
1:51 pm - 12:26 am
AXA
-
ORD
11h 35m
1 stop
$664American Airlines
Sat, Jul 18 - Wed, Jul 22
American Airlines Logo
5:59 pm - 1:11 pm
ORD
-
AXA
18h 12m
1 stop
American Airlines Logo
1:51 pm - 12:01 am
AXA
-
ORD
11h 10m
2 stops
$669American Airlines
Sat, Jul 18 - Wed, Jul 22
American Airlines Logo
5:00 am - 4:19 pm
ORD
-
AXA
10h 19m
1 stop
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$694American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
5:00 am - 1:11 pm
ORD
-
AXA
7h 11m
1 stop
American Airlines Logo
4:59 pm - 8:52 am
AXA
-
ORD
16h 53m
2 stops
$699American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
5:07 am - 4:19 pm
ORD
-
AXA
10h 12m
2 stops
American Airlines Logo
4:59 pm - 7:04 am
AXA
-
ORD
15h 05m
2 stops
$729American Airlines
Tue, Jul 7 - Wed, Jul 22
American Airlines Logo
7:07 pm - 2:18 pm
ORD
-
AXA
17h 11m
1 stop
American Airlines Logo
5:05 pm - 12:21 am
AXA
-
ORD
9h 16m
1 stop
$734American Airlines
Sat, Nov 14 - Sat, Nov 21
American Airlines Logo
8:45 pm - 2:18 pm
ORD
-
AXA
15h 33m
2 stops
American Airlines Logo
5:05 pm - 9:25 am
AXA
-
ORD
18h 20m
1 stop
$739American Airlines
Sat, Nov 14 - Sat, Nov 21
American Airlines Logo
5:59 pm - 4:19 pm
ORD
-
AXA
21h 20m
1 stop
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$741American Airlines
Sat, Jul 11 - Wed, Jul 15
American Airlines Logo
5:59 pm - 4:19 pm
ORD
-
AXA
21h 20m
1 stop
American Airlines Logo
4:59 pm - 7:38 am
AXA
-
ORD
15h 39m
2 stops
$745American Airlines
Sat, Jul 11 - Wed, Jul 15
American Airlines Logo
5:59 pm - 1:11 pm
ORD
-
AXA
18h 12m
1 stop
American Airlines Logo
12:40 pm - 10:59 pm
AXA
-
ORD
11h 19m
1 stop
$759American Airlines
Sat, Jul 25 - Sat, Aug 1

American Airlines flights from Chicago O'Hare Intl Airport to Anguilla

Our best American Airlines deals on Chicago O'Hare Intl Airport to Anguilla flight tickets
American Airlines
Jul 18
ORD5:59 pmChicago O'Hare Intl
18h 12m
1 stop
AXA1:11 pmThe Valley Wallblake Intl
Jul 22
AXA1:51 pmThe Valley Wallblake Intl
11h 35m
1 stop
ORD12:26 amChicago O'Hare Intl
$664
American Airlines
Jul 18
ORD5:59 pmChicago O'Hare Intl
18h 12m
1 stop
AXA1:11 pmThe Valley Wallblake Intl
Jul 22
AXA1:51 pmThe Valley Wallblake Intl
11h 10m
2 stops
ORD12:01 amChicago O'Hare Intl
$669
American Airlines
Jul 7
ORD5:00 amChicago O'Hare Intl
10h 19m
1 stop
AXA4:19 pmThe Valley Wallblake Intl
Jul 22
AXA4:59 pmThe Valley Wallblake Intl
17h 09m
1 stop
ORD9:08 amChicago O'Hare Intl
$694

JetBlue flights from Chicago O'Hare Intl Airport to Anguilla

Our best JetBlue deals on Chicago O'Hare Intl Airport to Anguilla flight tickets
JetBlue
Jul 30
ORD8:10 pmChicago O'Hare Intl
20h 25m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Aug 4
AXA9:46 amThe Valley Wallblake Intl
34h 44m
3 stops
ORD7:30 pmChicago O'Hare Intl
$1,454
JetBlue
Jul 31
ORD8:10 pmChicago O'Hare Intl
20h 25m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Aug 4
AXA9:46 amThe Valley Wallblake Intl
25h 20m
3 stops
ORD10:06 amChicago O'Hare Intl
$1,518
JetBlue
Jul 31
ORD10:56 amChicago O'Hare Intl
29h 39m
2 stops
AXA5:35 pmThe Valley Wallblake Intl
Aug 4
AXA9:46 amThe Valley Wallblake Intl
34h 44m
3 stops
ORD7:30 pmChicago O'Hare Intl
$1,744

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 May 28, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport 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

Sat 7/18

5:59 pm-1:11 pm

1 stop18h 12m

The Valley Wallblake Intl

Wed 7/22

1:51 pm-12:26 am

1 stop11h 35m

$664

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/18

5:59 pm-1:11 pm

1 stop18h 12m

The Valley Wallblake Intl

Wed 7/22

1:51 pm-12:01 am

2 stops11h 10m

$669

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:00 am-4:19 pm

1 stop10h 19m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-9:08 am

1 stop17h 09m

$694
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:00 am-1:11 pm

1 stop7h 11m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-8:52 am

2 stops16h 53m

$699

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 7/7

5:07 am-4:19 pm

2 stops10h 12m

The Valley Wallblake Intl

Wed 7/22

4:59 pm-7:04 am

2 stops15h 05m

$729

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 11/14

7:07 pm-2:18 pm

1 stop17h 11m

The Valley Wallblake Intl

Sat 11/21

5:05 pm-12:21 am

1 stop9h 16m

$734

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 11/14

8:45 pm-2:18 pm

2 stops15h 33m

The Valley Wallblake Intl

Sat 11/21

5:05 pm-9:25 am

1 stop18h 20m

$739

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/11

5:59 pm-4:19 pm

1 stop21h 20m

The Valley Wallblake Intl

Wed 7/15

4:59 pm-9:08 am

1 stop17h 09m

$741

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/11

5:59 pm-4:19 pm

1 stop21h 20m

The Valley Wallblake Intl

Wed 7/15

4:59 pm-7:38 am

2 stops15h 39m

$745

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 7/25

5:59 pm-1:11 pm

1 stop18h 12m

The Valley Wallblake Intl

Sat 8/1

12:40 pm-10:59 pm

1 stop11h 19m

$759

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Anguilla from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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 month to fly to Anguilla?

If you aren’t able to travel to Anguilla during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $0.

Cheap Chicago O'Hare Intl Airport to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Anguilla

Fastest flight time

10h 15m

Direct flights

None
The fastest flight from Chicago O'Hare Intl Airport to Anguilla takes 10h 15m
There are no direct flights from Chicago O'Hare Intl Airport to Anguilla. There are no popular flight routes from Chicago O'Hare Intl Airport to Anguilla.
Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Anguilla

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Anguilla?

    Prices for flights from Chicago O'Hare Intl Airport to Anguilla were last updated today.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Anguilla?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Anguilla.

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

    The necessary travel and health documents for your Anguilla trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Chicago O'Hare Intl Airport to Anguilla

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Anguilla with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $529Free CancellationRating
7.1
11,639 reviews
Search American Airlines flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Anguilla from Chicago.

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

All flight searches from Chicago to Anguilla on momondo can be filtered to show those which offer flexible booking policies.

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

momondo helps you find the best flight between Chicago and Anguilla by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Of course. momondo tracks the price of Chicago to Anguilla flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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