Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Anguilla from $669

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Anguilla departing on 7/1. 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

Discover deals from 900+ travel sites with momondo.

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 - 1:19 pm
ORD
-
AXA
7h 19m
1 stop
American Airlines Logo
4:59 pm - 12:26 am
AXA
-
ORD
8h 27m
1 stop
$669American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
5:10 am - 4:15 pm
ORD
-
AXA
10h 05m
2 stops
American Airlines Logo
4:59 pm - 12:26 am
AXA
-
ORD
8h 27m
1 stop
$674American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
6:00 pm - 1:19 pm
ORD
-
AXA
18h 19m
1 stop
American Airlines Logo
4:55 pm - 9:09 am
AXA
-
ORD
17h 14m
1 stop
$699American Airlines
Fri, Jun 19 - Thu, Jun 25
American Airlines Logo
6:10 am - 4:15 pm
ORD
-
AXA
9h 05m
1 stop
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$704American Airlines
Wed, Jul 1 - Mon, Jul 6
American Airlines Logo
5:10 am - 4:15 pm
ORD
-
AXA
10h 05m
2 stops
American Airlines Logo
4:59 pm - 6:30 am
AXA
-
ORD
14h 31m
2 stops
$709American Airlines
Wed, Jul 1 - Mon, Jul 6
American Airlines Logo
5:59 pm - 1:11 pm
ORD
-
AXA
18h 12m
1 stop
American Airlines Logo
4:59 pm - 9:08 am
AXA
-
ORD
17h 09m
1 stop
$759American Airlines
Mon, Jul 20 - Mon, Jul 27
American Airlines Logo
5:00 am - 4:19 pm
ORD
-
AXA
10h 19m
1 stop
American Airlines Logo
4:59 pm - 6:30 am
AXA
-
ORD
14h 31m
2 stops
$764American Airlines
Sun, Jul 19 - Sat, Jul 25
American Airlines Logo
6:59 am - 4:19 pm
ORD
-
AXA
8h 20m
1 stop
American Airlines Logo
4:59 pm - 12:25 am
AXA
-
ORD
8h 26m
1 stop
$809American Airlines
Sun, Jul 19 - Sat, Jul 25
American Airlines Logo
8:54 pm - 1:11 pm
ORD
-
AXA
15h 17m
2 stops
American Airlines Logo
4:59 pm - 8:52 am
AXA
-
ORD
16h 53m
2 stops
$814American Airlines
Mon, Jul 20 - Mon, Jul 27
American Airlines Logo
5:10 am - 4:19 pm
ORD
-
AXA
10h 09m
2 stops
American Airlines Logo
4:59 pm - 6:30 am
AXA
-
ORD
14h 31m
2 stops
$824American Airlines
Sun, Jul 19 - Sat, Jul 25

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

American Airlines flights from Chicago to Anguilla

Our best American Airlines deals on Chicago to Anguilla flight tickets
American Airlines
Jul 1
ORD5:00 amChicago O'Hare Intl
7h 19m
1 stop
AXA1:19 pmThe Valley Wallblake Intl
Jul 7
AXA4:59 pmThe Valley Wallblake Intl
8h 27m
1 stop
ORD12:26 amChicago O'Hare Intl
$669
American Airlines
Jul 1
ORD5:10 amChicago O'Hare Intl
10h 05m
2 stops
AXA4:15 pmThe Valley Wallblake Intl
Jul 7
AXA4:59 pmThe Valley Wallblake Intl
8h 27m
1 stop
ORD12:26 amChicago O'Hare Intl
$674
American Airlines
Jun 19
ORD6:00 pmChicago O'Hare Intl
18h 19m
1 stop
AXA1:19 pmThe Valley Wallblake Intl
Jun 25
AXA4:55 pmThe Valley Wallblake Intl
17h 14m
1 stop
ORD9:09 amChicago O'Hare Intl
$699

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 April 30, 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
Quickest round-trip

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 7/1

5:00 am-1:19 pm

1 stop7h 19m

The Valley Wallblake Intl

Tue 7/7

4:59 pm-12:26 am

1 stop8h 27m

$669

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 7/1

5:10 am-4:15 pm

2 stops10h 05m

The Valley Wallblake Intl

Tue 7/7

4:59 pm-12:26 am

1 stop8h 27m

$674

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 6/19

6:00 pm-1:19 pm

1 stop18h 19m

The Valley Wallblake Intl

Thu 6/25

4:55 pm-9:09 am

1 stop17h 14m

$699

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 7/1

6:10 am-4:15 pm

1 stop9h 05m

The Valley Wallblake Intl

Mon 7/6

4:59 pm-9:08 am

1 stop17h 09m

$704

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 7/1

5:10 am-4:15 pm

2 stops10h 05m

The Valley Wallblake Intl

Mon 7/6

4:59 pm-6:30 am

2 stops14h 31m

$709

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 7/20

5:59 pm-1:11 pm

1 stop18h 12m

The Valley Wallblake Intl

Mon 7/27

4:59 pm-9:08 am

1 stop17h 09m

$759

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 7/19

5:00 am-4:19 pm

1 stop10h 19m

The Valley Wallblake Intl

Sat 7/25

4:59 pm-6:30 am

2 stops14h 31m

$764

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 7/19

6:59 am-4:19 pm

1 stop8h 20m

The Valley Wallblake Intl

Sat 7/25

4:59 pm-12:25 am

1 stop8h 26m

$809

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Mon 7/20

8:54 pm-1:11 pm

2 stops15h 17m

The Valley Wallblake Intl

Mon 7/27

4:59 pm-8:52 am

2 stops16h 53m

$814

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sun 7/19

5:10 am-4:19 pm

2 stops10h 09m

The Valley Wallblake Intl

Sat 7/25

4:59 pm-6:30 am

2 stops14h 31m

$824

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 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 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

8h 27m

Direct flights

None
The fastest flight from Chicago to Anguilla takes 8h 27m
There are no direct flights from Chicago to Anguilla. There are no popular flight routes from Chicago to Anguilla.
Search flight deals

Frequently asked questions about flying from Chicago to Anguilla

  • 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
11,681 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.

An easier way to manage your Anguilla trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 5/30
Sat 6/6
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Anguilla

Popular cities in Anguilla

Popular flights according to clicks in the last 7 days on momondo
Flights to The Valleyfrom $617