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Cheap flights from Chicago (CHI) to Anguilla from $415

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — AXA
May 16 — May 231
From?
To?
Thu 5/16
Thu 5/23
1 adult, Economy
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What is the cheapest month to fly from Chicago to Anguilla?

November is one of the best times of the year to fly to Anguilla from Chicago. Prices for November average $923 per person but you can even find prices for as low as $524. The most expensive prices can be found in the month of March. Opting for a November flight can save you 52% on your journey compared to booking in March

When is the cheapest time to fly from Chicago to Anguilla (CHI - AI)?

When flying from Chicago to Anguilla, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap American Airlines flights from Chicago to Anguilla

Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Anguilla. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Tue 5/287:00 amORD - AXA
1 stop7h 05mAmerican Airlines
Tue 6/43:45 pmAXA - ORD
1 stop18h 15mAmerican Airlines
Deal found 5/10$415
Tue 5/285:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Tue 6/42:00 pmAXA - ORD
1 stop8h 28mAmerican Airlines
Deal found 5/10$418
Tue 5/285:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Tue 6/43:45 pmAXA - ORD
2 stops16h 38mAmerican Airlines
Deal found 5/10$468
Tue 6/45:00 amORD - AXA
1 stop9h 05mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
1 stop8h 48mAmerican Airlines
Deal found 5/9$517
Tue 6/45:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
2 stops19h 04mAmerican Airlines
Deal found 5/9$519
Tue 6/45:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
1 stop8h 48mAmerican Airlines
Deal found 5/9$520
Sat 10/125:00 amORD - AXA
1 stop7h 22mAmerican Airlines
Sat 10/192:50 pmAXA - ORD
1 stop8h 15mAmerican Airlines
Deal found 5/10$699
Sat 10/125:00 amORD - AXA
1 stop7h 22mAmerican Airlines
Sat 10/192:50 pmAXA - ORD
2 stops17h 50mAmerican Airlines
Deal found 5/10$704
Fri 5/177:00 amORD - AXA
1 stop7h 05mAmerican Airlines
Fri 5/243:45 pmAXA - ORD
1 stop18h 22mAmerican Airlines
Deal found 5/10$730

Cheap Chicago to Anguilla flights in May & June 2024

Find cheap flight options from Chicago to Anguilla specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,684,066 searches. Prices were last updated on May 11, 2024.
Tue 5/287:00 amORD - AXA
1 stop7h 05mAmerican Airlines
Tue 6/43:45 pmAXA - ORD
1 stop18h 15mAmerican Airlines
Deal found 5/10$415
Tue 5/285:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Tue 6/42:00 pmAXA - ORD
1 stop8h 28mAmerican Airlines
Deal found 5/10$418
Tue 5/285:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Tue 6/43:45 pmAXA - ORD
2 stops16h 38mAmerican Airlines
Deal found 5/10$468
Tue 6/45:00 amORD - AXA
1 stop9h 05mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
1 stop8h 48mAmerican Airlines
Deal found 5/9$517
Tue 6/45:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
2 stops19h 04mAmerican Airlines
Deal found 5/9$519
Tue 6/45:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
1 stop8h 48mAmerican Airlines
Deal found 5/9$520
Fri 5/1711:10 amORD - AXA
1 stop23h 20mMultiple Airlines
Fri 5/241:45 pmAXA - ORD
2 stops34h 44mMultiple Airlines
Deal found 5/10$656
Fri 5/177:00 amORD - AXA
1 stop7h 05mAmerican Airlines
Fri 5/243:45 pmAXA - ORD
1 stop18h 22mAmerican Airlines
Deal found 5/10$730
Fri 5/175:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Fri 5/243:45 pmAXA - ORD
2 stops21h 23mAmerican Airlines
Deal found 5/10$912

Chicago to Anguilla 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Anguilla in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Tue 5/287:00 amORD - AXA
1 stop7h 05mAmerican Airlines
Tue 6/43:45 pmAXA - ORD
1 stop18h 15mAmerican Airlines
Deal found 5/10$415
Tue 5/285:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Tue 6/42:00 pmAXA - ORD
1 stop8h 28mAmerican Airlines
Deal found 5/10$418
Tue 5/285:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Tue 6/43:45 pmAXA - ORD
2 stops16h 38mAmerican Airlines
Deal found 5/10$468
Tue 6/45:00 amORD - AXA
1 stop9h 05mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
1 stop8h 48mAmerican Airlines
Deal found 5/9$517
Tue 6/45:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
2 stops19h 04mAmerican Airlines
Deal found 5/9$519
Tue 6/45:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Wed 6/54:05 pmAXA - ORD
1 stop8h 48mAmerican Airlines
Deal found 5/9$520
Wed 12/116:59 amORD - AXA
1 stop7h 09mAmerican Airlines
Tue 12/175:05 pmAXA - ORD
1 stop17h 59mAmerican Airlines
Deal found 5/10$539
Wed 12/115:25 amORD - AXA
2 stops8h 43mAmerican Airlines
Tue 12/175:05 pmAXA - ORD
2 stops17h 50mAmerican Airlines
Deal found 5/10$541
Wed 12/116:59 amORD - AXA
1 stop7h 09mAmerican Airlines
Tue 12/175:05 pmAXA - ORD
2 stops17h 50mAmerican Airlines
Deal found 5/10$542

Chicago to Anguilla flights leaving soon

Find last-minute flight options from Chicago to Anguilla for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Fri 5/1711:10 amORD - AXA
1 stop23h 20mMultiple Airlines
Fri 5/241:45 pmAXA - ORD
2 stops34h 44mMultiple Airlines
Deal found 5/10$656
Fri 5/177:00 amORD - AXA
1 stop7h 05mAmerican Airlines
Fri 5/243:45 pmAXA - ORD
1 stop18h 22mAmerican Airlines
Deal found 5/10$730
Fri 5/175:15 amORD - AXA
2 stops8h 50mAmerican Airlines
Fri 5/243:45 pmAXA - ORD
2 stops21h 23mAmerican Airlines
Deal found 5/10$912

One-way flights to Anguilla from Chicago

Search for one-way flight options from Chicago to Anguilla. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Sat 9/79:28 pmORD - AXA
3 stops40h 12mMultiple Airlines
Deal found 5/10$573

Find flights from Chicago to Anguilla within your budget

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, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$415 - $704

Route

Depart

Return

Price

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 5/28

1 stop7h 05m

The Valley Wallblake Intl

Tue 6/4

1 stop18h 15m

$415

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 5/28

2 stops8h 50m

The Valley Wallblake Intl

Tue 6/4

1 stop8h 28m

$418

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 5/28

2 stops8h 50m

The Valley Wallblake Intl

Tue 6/4

2 stops16h 38m

$468

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 6/4

1 stop9h 05m

The Valley Wallblake Intl

Wed 6/5

1 stop8h 48m

$517

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 6/4

2 stops8h 50m

The Valley Wallblake Intl

Wed 6/5

2 stops19h 04m

$519

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 6/4

2 stops8h 50m

The Valley Wallblake Intl

Wed 6/5

1 stop8h 48m

$520

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 10/12

1 stop7h 22m

The Valley Wallblake Intl

Sat 10/19

1 stop8h 15m

$699

Chicago O'Hare IntlThe Valley Wallblake Intl

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Sat 10/12

1 stop7h 22m

The Valley Wallblake Intl

Sat 10/19

2 stops17h 50m

$704

Flights are sorted by cheapest first

Deals found on 5/10

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Anguilla

Get insights into the airlines that provide service to Anguilla. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Anguilla. Reviews last updated May 11, 2024.
American Airlines
7.3
Good
14,639 reviews
Check prices

Crew

8.0

Comfort

7.2

Entertainment

7.1

Overall

7.3

Boarding

7.6

Food

6.6

Reviews

1 / 10

Entertainment was ok, no delays either. The food was just ok, the trays were dirty and overall the plane seemed dated.

American Airlines
7.3
Good
14,639 reviews
American Airlines
7.3
Good
14,639 reviews
Check prices

Crew

8.0

Comfort

7.2

Entertainment

7.1

Overall

7.3

Boarding

7.6

Food

6.6

Reviews

1 / 10

Entertainment was ok, no delays either. The food was just ok, the trays were dirty and overall the plane seemed dated.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Anguilla. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago to Anguilla for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago to Anguilla for under $500. The cheapest flight booked recently is on American Airlines for just $415, but on average you can expect to pay $532.

  • Are there last-minute flights available from Chicago to Anguilla for under $700?

    There are currently 3+ open flights from Chicago to Anguilla within the next 7 days for less than $700.

  • What does ORD to AXA mean?

    ORD and AXA are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. ORD to AXA refers to a flight route from Chicago O'Hare Intl Airport to The Valley Wallblake Intl Airport. Ready for more IATA code knowledge? These are related airports for your current travel destination: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

  • Can I find deals for flights from Chicago to Anguilla that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Anguilla flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Anguilla with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Anguilla flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Anguilla that include hotel bookings?

    Yes. In addition to deals on Chicago to Anguilla flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Anguilla?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Anguilla.

  • Can I find deals for business class flights from Chicago to Anguilla?

    Yes. Cheapflights offers flight deals from Chicago to Anguilla by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Anguilla that allow pets onboard?

    Many airlines flying from Chicago to Anguilla offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Anguilla?

    Yes, you can often find last-minute deals on Chicago to Anguilla flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Anguilla flight deals updated?

    The Chicago to Anguilla flight deals you see on this page were last updated on 5/11.

See more FAQs

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Top airline flying from Chicago to Anguilla

Discover the top airline that operate flights from Chicago to Anguilla. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$564Average$741FlexibilityNo cancel feeOn-time71%
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Search flights from Chicago to Anguilla by cabin class

Find flights from Chicago to Anguilla, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Fly with Cheapflights

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How does Cheapflights help users find flights from Chicago to Anguilla?

When you search for this flight from Chicago to Anguilla, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Anguilla?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Anguilla from Chicago.

Can Cheapflights find flights from Chicago to Anguilla with no change fees?

Certainly. Search results for flights to Anguilla from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago to Anguilla become cheaper?

Yes! Start tracking prices for Chicago to Anguilla flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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