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Cheap flights from Chicago to Anguilla from $345

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 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
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
5:00 am - 4:26 pm
ORD
-
AXA
9h 26m
1 stop
American Airlines Logo
5:10 pm - 12:37 am
AXA
-
ORD
9h 27m
1 stop
$536American Airlines
Mon, Feb 9 - Tue, Feb 17
American Airlines Logo
9:09 pm - 2:23 pm
ORD
-
AXA
15h 14m
2 stops
American Airlines Logo
5:10 pm - 7:24 am
AXA
-
ORD
16h 14m
2 stops
$576American Airlines
Mon, Feb 9 - Tue, Feb 17
American Airlines Logo
6:59 pm - 2:30 pm
ORD
-
AXA
17h 31m
1 stop
American Airlines Logo
5:10 pm - 12:37 am
AXA
-
ORD
9h 27m
1 stop
$578American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
5:00 am - 2:30 pm
ORD
-
AXA
7h 30m
1 stop
American Airlines Logo
5:10 pm - 7:25 am
AXA
-
ORD
16h 15m
2 stops
$583American Airlines
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
5:00 am - 4:28 pm
ORD
-
AXA
9h 28m
1 stop
American Airlines Logo
5:10 pm - 12:37 am
AXA
-
ORD
9h 27m
1 stop
$603American Airlines
Mon, Feb 23 - Mon, Mar 2
American Airlines Logo
10:15 pm - 2:30 pm
ORD
-
AXA
14h 15m
2 stops
American Airlines Logo
5:10 pm - 9:55 am
AXA
-
ORD
18h 45m
1 stop
$608American Airlines
Mon, Feb 23 - Mon, Mar 2
American Airlines Logo
6:58 pm - 1:15 pm
ORD
-
AXA
17h 17m
1 stop
American Airlines Logo
4:57 pm - 12:27 am
AXA
-
ORD
8h 30m
1 stop
$619American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
8:44 pm - 1:15 pm
ORD
-
AXA
15h 31m
2 stops
American Airlines Logo
4:57 pm - 7:33 am
AXA
-
ORD
15h 36m
2 stops
$624American Airlines
Sat, Apr 11 - Sat, Apr 18
American Airlines Logo
3:55 pm - 2:23 pm
ORD
-
AXA
20h 28m
2 stops
American Airlines Logo
5:10 pm - 12:37 am
AXA
-
ORD
9h 27m
1 stop
$626American Airlines
Mon, Feb 9 - Tue, Feb 17
American Airlines Logo
5:00 am - 3:29 pm
ORD
-
AXA
9h 29m
2 stops
American Airlines Logo
4:57 pm - 12:27 am
AXA
-
ORD
8h 30m
1 stop
$629American Airlines
Sun, Apr 5 - Sun, Apr 12

United Airlines flights from Chicago to Anguilla

Our best United Airlines deals on Chicago to Anguilla flight tickets
United Airlines
Feb 8
ORD6:17 pmChicago O'Hare Intl
21h 28m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Feb 12
AXA9:00 amThe Valley Wallblake Intl
11h 45m
1 stop
ORD6:45 pmChicago O'Hare Intl
$1,858
United Airlines
Feb 8
ORD6:17 pmChicago O'Hare Intl
21h 28m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Feb 12
AXA9:00 amThe Valley Wallblake Intl
16h 43m
2 stops
ORD11:43 pmChicago O'Hare Intl
$2,582
United Airlines
Feb 8
ORD6:17 pmChicago O'Hare Intl
21h 28m
2 stops
AXA5:45 pmThe Valley Wallblake Intl
Feb 12
AXA9:00 amThe Valley Wallblake Intl
11h 41m
2 stops
ORD6:41 pmChicago O'Hare Intl
$4,585

American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets
American Airlines
Feb 9
ORD5:00 amChicago O'Hare Intl
9h 26m
1 stop
AXA4:26 pmThe Valley Wallblake Intl
Feb 17
AXA5:10 pmThe Valley Wallblake Intl
9h 27m
1 stop
ORD12:37 amChicago O'Hare Intl
$536
American Airlines
Feb 9
ORD9:09 pmChicago O'Hare Intl
15h 14m
2 stops
AXA2:23 pmThe Valley Wallblake Intl
Feb 17
AXA5:10 pmThe Valley Wallblake Intl
16h 14m
2 stops
ORD7:24 amChicago O'Hare Intl
$576
American Airlines
Feb 22
ORD6:59 pmChicago O'Hare Intl
17h 31m
1 stop
AXA2:30 pmThe Valley Wallblake Intl
Feb 25
AXA5:10 pmThe Valley Wallblake Intl
9h 27m
1 stop
ORD12:37 amChicago O'Hare Intl
$578

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 January 28, 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

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/9

5:00 am-4:26 pm

1 stop9h 26m

The Valley Wallblake Intl

Tue 2/17

5:10 pm-12:37 am

1 stop9h 27m

$536

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/9

9:09 pm-2:23 pm

2 stops15h 14m

The Valley Wallblake Intl

Tue 2/17

5:10 pm-7:24 am

2 stops16h 14m

$576

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 2/22

6:59 pm-2:30 pm

1 stop17h 31m

The Valley Wallblake Intl

Wed 2/25

5:10 pm-12:37 am

1 stop9h 27m

$578

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 2/22

5:00 am-2:30 pm

1 stop7h 30m

The Valley Wallblake Intl

Wed 2/25

5:10 pm-7:25 am

2 stops16h 15m

$583

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/23

5:00 am-4:28 pm

1 stop9h 28m

The Valley Wallblake Intl

Mon 3/2

5:10 pm-12:37 am

1 stop9h 27m

$603

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/23

10:15 pm-2:30 pm

2 stops14h 15m

The Valley Wallblake Intl

Mon 3/2

5:10 pm-9:55 am

1 stop18h 45m

$608

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/11

6:58 pm-1:15 pm

1 stop17h 17m

The Valley Wallblake Intl

Sat 4/18

4:57 pm-12:27 am

1 stop8h 30m

$619

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 4/11

8:44 pm-1:15 pm

2 stops15h 31m

The Valley Wallblake Intl

Sat 4/18

4:57 pm-7:33 am

2 stops15h 36m

$624

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 2/9

3:55 pm-2:23 pm

2 stops20h 28m

The Valley Wallblake Intl

Tue 2/17

5:10 pm-12:37 am

1 stop9h 27m

$626

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 4/5

5:00 am-3:29 pm

2 stops9h 29m

The Valley Wallblake Intl

Sun 4/12

4:57 pm-12:27 am

1 stop8h 30m

$629

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 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

7h 15m

Direct flights

None
The fastest flight from Chicago to Anguilla takes 7h 15m
There are no direct flights from Chicago to Anguilla. There are no popular flight routes from Chicago to Anguilla.
Search flight deals

  • 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 $597Free CancellationRating
7.2
11,201 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 flights according to clicks in the last 7 days on momondo
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