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Flights from Chicago to Anguilla, Anguilla Last modified: Sep 29, 2016 1:00 AM

Chicago to Anguilla Last modified: Sep 19, 2016 4:35 AM

We've scanned 18,984,511,576 round trip itineraries and found the cheapest flights from Chicago to Anguilla. American & Delta frequently offer the best deals on Chicago to Anguilla flights, or select your preferred carrier below to see the cheapest days to fly.

American
CHIAXA
Sat 1/7
2 stops
AXACHI
Sat 1/14
2 stops
$578
Select
Major Airlines
CHIAXA
Sat 11/5
2 stops
AXACHI
Sat 11/12
2 stops
$592
Select
Major Airlines
CHIAXA
Wed 1/4
2 stops
AXACHI
Sun 1/8
2 stops
$592
Select
JetBlue
CHIAXA
Sat 1/7
2 stops
AXACHI
Sun 1/15
2 stops
$616
Select
United
CHIAXA
Fri 1/13
1 stop
AXACHI
Thu 1/19
1 stop
$1,241
Select

How Much is a Flight from Chicago to Anguilla?

Unfortunately we weren't able to find enough recent prices to provide a meaningful average. Running an airfare search now will update and compare prices. Find Flights

Where To Buy Cheap Flights from Chicago to Anguilla?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we thinking FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to Anguilla based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from Chicago to Anguilla?

The chart below shows up-to-date information regarding how far in advance to book your flight from Chicago to Anguilla.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $0 $0
7-14 days $0 $0
14-21 days $0 $0
21-30 days $0 $0
30-60 days $0 $587
60-90 days $0 $580
90+ days $0 $578

Cheapest Day To Fly from Chicago to Anguilla

We've examined 18,991,239,476 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from Chicago to Anguilla is Wednesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$580 $580 $585

Compare Flight Prices from Chicago to Anguilla by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for Chicago to Anguilla flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
November Chicago Anguilla American 11/30/16 12/8/16 1 $580
December Chicago Anguilla American 12/2/16 12/8/16 2 $580
January Chicago Anguilla American 1/7/17 1/14/17 2 $578
February Chicago Anguilla American 2/25/17 3/4/17 3 $580
March Chicago Anguilla American 3/1/17 3/5/17 1 $587
April Chicago Anguilla American 4/22/17 4/29/17 2 $589
May Chicago Anguilla American 5/6/17 5/13/17 2 $590
June Chicago Anguilla American 6/10/17 6/17/17 2 $589

Cheap Last Minute Flights from Chicago to Anguilla

Well that's unexpected... we weren't able to find enough weekend deals to make a good comparison. Run an airfare search now to update and compare prices. Find Flights

Connecting Flights vs Direct Flights from Chicago to Anguilla

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from Chicago to Anguilla is $776.

The average price for direct flights from Chicago to Anguilla is not available.

One Way Flights vs Round Trip Flights from Chicago to Anguilla

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Anguilla. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Anguilla is not available.

The average price for round trip flights from Chicago to Anguilla is $776.

Chicago to Anguilla Flight Questions

Below are some common questions that asked about this flight route:

Question: What are the most popular connecting cities when flying from Chicago to Anguilla?
Answer: Antigua, AG

Airlines in Chicago flying to Anguilla Last modified: Sep 29, 2016 1:00 AMNumber of routes searched: 0Number of itineraries searched: 0

Wondering which airlines fly out of Chicago to Anguilla? We've gathered the average price of Chicago airlines with flights to Anguilla. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

    Chicago to Anguilla Airports

    These are the major commercial airports we're currently monitoring in Chicago and Anguilla. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

    Farecompare Research Tools

    FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

    Cheap Domestic Flights from Chicago - CHI

    FlightsAirlineLowest Price
    Flights from Chicago to San Juan American, JetBlue, Delta, Spirit, United $100
    Flights from Chicago to Ft Lauderdale American, JetBlue, Delta, Spirit, United $117
    Flights from Chicago to Tampa American, Delta, Frontier, Spirit, United $87
    Flights from Chicago to Newark American, Delta, United $147
    Flights from Chicago to Ft Myers American, Delta, Spirit, United $157
    Flights from Chicago to Detroit American, Delta $177
    Flights from Chicago to Aguadilla JetBlue, Spirit, United $334
    Flights from Chicago to Charlotte American, Alaska, Delta, Frontier, United $85
    Flights from Chicago to Philadelphia American, JetBlue, Delta, Frontier, Spirit $97

    Cheap International Flights from Chicago - CHI

    FlightsAirlineLowest Price
    Flights from Chicago to St Maarten American, Air Canada, JetBlue, Delta, United, WestJet $497
    Flights from Chicago to St Thomas Island American, Delta, Spirit, United $317
    Flights from Chicago to St BarthelemyCheck Dates
    Flights from Chicago to St Kitts American, Air Canada, British Airways, Delta, United $639
    Flights from Chicago to St Croix Island American, Delta, United $331
    Flights from Chicago to Punta Cana American, Air Canada, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet $318
    Flights from Chicago to Antigua Air Canada, British Airways, Delta, United $514
    Flights from Chicago to NevisCheck Dates
    Flights from Chicago to St Lucia American, Air Canada, JetBlue, Delta, United $510
    Flights from Chicago to Cancun American, Air Canada, AeroMexico, JetBlue, British Airways, Copa, Delta, Frontier, Spirit, United, WestJet, Volaris $304
    Flights from Chicago to Aruba American, Air Canada, Avianca, JetBlue, British Airways, Delta, Spirit, United $376
    Flights from Chicago to Barbados Air Canada, JetBlue, British Airways, Delta $340
    Flights from Chicago to Beef IslandCheck Dates

    Cheap Domestic Flights to Anguilla - AXA

    FlightsAirlineLowest Price
    Flights from Indianapolis to San Juan American, Delta, United $287
    Flights from Milwaukee to San Juan American, Delta, United $288

    Cheap International Flights to Anguilla - AXA

    FlightsAirlineLowest Price
    Flights from Indianapolis to St Maarten American, Air Canada, Copa, Delta, United $609
    Flights from Milwaukee to St Maarten American, Air Canada, Copa, Delta, United $564
    Flights from Indianapolis to St Kitts American, Air Canada, Delta, United $735
    Flights from Indianapolis to St Thomas Island American, Delta, United $395
    Flights from Milwaukee to St Thomas Island American, Delta, United $418
    Flights from Indianapolis to Antigua American, Air Canada, Delta, United $525
    Cheap Flights from Chicago to Anguilla