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Cheap flights from Chicago O'Hare Intl Airport to Anguilla from $480

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 4/6. 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 O'Hare Intl Airport to Anguilla

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
5:05 am - 4:40 pm
ORD
-
AXA
10h 35m
2 stops
Multiple Airlines Logo
10:00 am - 12:24 am
AXA
-
ORD
15h 24m
2 stops
$575Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
5:05 am - 4:40 pm
ORD
-
AXA
10h 35m
2 stops
Multiple Airlines Logo
12:00 pm - 11:07 pm
AXA
-
ORD
12h 07m
3 stops
$622Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
1:59 pm - 9:29 pm
AXA
-
ORD
8h 30m
1 stop
$664American Airlines
Sun, May 17 - Thu, May 21
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
2 stops
American Airlines Logo
1:59 pm - 9:29 pm
AXA
-
ORD
8h 30m
1 stop
$669American Airlines
Sun, May 17 - Thu, May 21
American Airlines Logo
5:10 am - 4:15 pm
ORD
-
AXA
10h 05m
2 stops
American Airlines Logo
4:55 pm - 7:10 am
AXA
-
ORD
15h 15m
2 stops
$674American Airlines
Wed, May 27 - Wed, Jun 10
American Airlines Logo
5:00 am - 4:17 pm
ORD
-
AXA
10h 17m
1 stop
American Airlines Logo
1:59 pm - 12:24 am
AXA
-
ORD
11h 25m
1 stop
$694American Airlines
Sun, May 17 - Thu, May 21
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
AXA
15h 29m
2 stops
American Airlines Logo
1:59 pm - 10:33 pm
AXA
-
ORD
9h 34m
1 stop
$699American Airlines
Sun, May 17 - Thu, May 21
American Airlines Logo
6:00 pm - 1:19 pm
ORD
-
AXA
18h 19m
1 stop
American Airlines Logo
4:55 pm - 7:10 am
AXA
-
ORD
15h 15m
2 stops
$704American Airlines
Thu, May 28 - Wed, Jun 10
American Airlines Logo
7:00 pm - 1:15 pm
ORD
-
AXA
17h 15m
1 stop
American Airlines Logo
1:55 pm - 12:25 am
AXA
-
ORD
11h 30m
1 stop
$764American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
8:46 pm - 1:15 pm
ORD
-
AXA
15h 29m
2 stops
American Airlines Logo
4:57 pm - 7:31 am
AXA
-
ORD
15h 34m
2 stops
$769American Airlines
Thu, May 14 - Mon, May 18

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
May 17
ORD7:00 pmChicago O'Hare Intl
17h 15m
1 stop
AXA1:15 pmThe Valley Wallblake Intl
May 21
AXA1:59 pmThe Valley Wallblake Intl
8h 30m
1 stop
ORD9:29 pmChicago O'Hare Intl
$664
American Airlines
May 17
ORD5:00 amChicago O'Hare Intl
10h 17m
2 stops
AXA4:17 pmThe Valley Wallblake Intl
May 21
AXA1:59 pmThe Valley Wallblake Intl
8h 30m
1 stop
ORD9:29 pmChicago O'Hare Intl
$669
American Airlines
May 27
ORD5:10 amChicago O'Hare Intl
10h 05m
2 stops
AXA4:15 pmThe Valley Wallblake Intl
Jun 10
AXA4:55 pmThe Valley Wallblake Intl
15h 15m
2 stops
ORD7:10 amChicago O'Hare Intl
$674

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
Apr 6
ORD8:58 amChicago O'Hare Intl
31h 47m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Apr 11
AXA9:00 amThe Valley Wallblake Intl
24h 08m
3 stops
ORD8:08 amChicago O'Hare Intl
$1,667
JetBlue
Apr 6
ORD8:58 amChicago O'Hare Intl
31h 47m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Apr 11
AXA9:00 amThe Valley Wallblake Intl
24h 08m
3 stops
ORD8:08 amChicago O'Hare Intl
$1,695
JetBlue
Apr 11
ORD8:58 amChicago O'Hare Intl
31h 47m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Apr 18
AXA9:00 amThe Valley Wallblake Intl
25h 00m
3 stops
ORD9:00 amChicago O'Hare Intl
$1,716

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 April 1, 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 4/18

5:05 am-4:40 pm

2 stops10h 35m

The Valley Wallblake Intl

Sat 4/25

10:00 am-12:24 am

2 stops15h 24m

$575

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/18

5:05 am-4:40 pm

2 stops10h 35m

The Valley Wallblake Intl

Sat 4/25

12:00 pm-11:07 pm

3 stops12h 07m

$622

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 5/17

7:00 pm-1:15 pm

1 stop17h 15m

The Valley Wallblake Intl

Thu 5/21

1:59 pm-9:29 pm

1 stop8h 30m

$664
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 5/17

5:00 am-4:17 pm

2 stops10h 17m

The Valley Wallblake Intl

Thu 5/21

1:59 pm-9:29 pm

1 stop8h 30m

$669

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 5/27

5:10 am-4:15 pm

2 stops10h 05m

The Valley Wallblake Intl

Wed 6/10

4:55 pm-7:10 am

2 stops15h 15m

$674

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 5/17

5:00 am-4:17 pm

1 stop10h 17m

The Valley Wallblake Intl

Thu 5/21

1:59 pm-12:24 am

1 stop11h 25m

$694

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 5/17

8:46 pm-1:15 pm

2 stops15h 29m

The Valley Wallblake Intl

Thu 5/21

1:59 pm-10:33 pm

1 stop9h 34m

$699

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 5/28

6:00 pm-1:19 pm

1 stop18h 19m

The Valley Wallblake Intl

Wed 6/10

4:55 pm-7:10 am

2 stops15h 15m

$704

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 5/14

7:00 pm-1:15 pm

1 stop17h 15m

The Valley Wallblake Intl

Mon 5/18

1:55 pm-12:25 am

1 stop11h 30m

$764

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Thu 5/14

8:46 pm-1:15 pm

2 stops15h 29m

The Valley Wallblake Intl

Mon 5/18

4:57 pm-7:31 am

2 stops15h 34m

$769

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 airline that flies from Chicago O'Hare Intl to Anguilla?

American Airlines and United Airlines are the most popular carriers operating from Chicago O'Hare Intl to Anguilla

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

7h 42m

Direct flights

None
The fastest flight from Chicago O'Hare Intl Airport to Anguilla takes 7h 42m
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

  • 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 $597Free CancellationRating
7.1
11,545 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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