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Anguilla

$446+ Cheap flights from Chicago (CHI) to Anguilla

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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — AXA
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Chicago to Anguilla

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Anguilla (AI0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

Find flight deals from Chicago to Anguilla

Cheapest flights from Chicago to Anguilla
Explore the most affordable flight options available from Chicago to Anguilla. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/69:32 pmORD - AXA
2 stops14h 38mMultiple Airlines
Wed 12/1112:50 pmAXA - ORD
1 stop30h 57mMultiple Airlines
Deal found 11/20$446
This United Airlines deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/31:55 pmORD - AXA
2 stops20h 20mUnited Airlines
Sat 12/72:45 pmAXA - ORD
1 stop7h 26mUnited Airlines
Deal found 11/20$779
This American Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/116:45 pmORD - AXA
1 stop18h 00mAmerican Airlines
Tue 12/173:25 pmAXA - ORD
1 stop10h 33mAmerican Airlines
Deal found 11/19$801

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 2,629,791 searches. Data last updated November 20, 2024.

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ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Fri 12/6

9:32 pm-2:10 pm

2 stops14h 38m

The Valley Wallblake Intl

Wed 12/11

12:50 pm-5:47 pm

1 stop30h 57m

$446

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Tue 12/3

12:53 pm-12:15 pm

2 stops21h 22m

The Valley Wallblake Intl

Sat 12/7

2:45 pm-9:43 am

2 stops20h 58m

$779

ChicagoThe Valley

ORD - AXA

ORDAXA

Chicago O'Hare Intl

Wed 12/11

6:45 pm-2:45 pm

1 stop18h 00m

The Valley Wallblake Intl

Tue 12/17

3:25 pm-11:58 pm

1 stop10h 33m

$801

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Best time to book a flight from Chicago to Anguilla

Have a flexible travel schedule? Discover the best time to fly to Anguilla from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Anguilla

Get recent, data-driven insights about flights from Chicago to Anguilla including ideal travel times, pricing trends, and more.

Rainfall in Anguilla by month

Plan your trip to Anguilla by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Anguilla ranges from 1.6 - 4.3 inches per month. August is typically the wettest month, when rainfall can reach 4.3 in. February is typically the driest time to visit Anguilla when rainfall is around 1.6 in.

Temperature in Anguilla by month

Plan your trip to Anguilla by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Anguilla, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 78.8 F).

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 November 20, 2024.
United Airlines
7.4
Good
9,171 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Reviews

1 / 10

Good boarding process. (Nice to be able to buy Group 2 boarding option.) Plane was clean. Tried to avoid full flight by flying on Saturday, but plane was full anyway. Gate area in Houston should have charging options. Should be a lounge for people with American Express Platinum Card in Houston Airport.

United Airlines
7.4
Good
9,171 reviews
United Airlines
7.4
Good
9,171 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Reviews

1 / 10

Good boarding process. (Nice to be able to buy Group 2 boarding option.) Plane was clean. Tried to avoid full flight by flying on Saturday, but plane was full anyway. Gate area in Houston should have charging options. Should be a lounge for people with American Express Platinum Card in Houston Airport.

American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
9,171 reviews

Crew

8.1

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.7

Reviews

1 / 10

Good boarding process. (Nice to be able to buy Group 2 boarding option.) Plane was clean. Tried to avoid full flight by flying on Saturday, but plane was full anyway. Gate area in Houston should have charging options. Should be a lounge for people with American Express Platinum Card in Houston Airport.

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 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.

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Alternative routes for Chicago to Anguilla

See prices for flight routes from nearby airports that may be better suited for you.
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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$565Average$749FlexibilityNo cancel feeOn-time71%
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