Cheap flights from Chicago to Anguilla from $335
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 7/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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American Airlines flights from Chicago to Anguilla
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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 day to depart on your flight to Anguilla?
The cheapest day to depart from Chicago to Anguilla is on a Friday when prices can be found for as low as $650. The most expensive day to fly to Anguilla is Saturday, with ticket prices averaging around $990.
What is the cheapest time of day to depart on your flight to Anguilla?
Flying to Anguilla from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $607 when looking at flights departing in the afternoon. Flights in the morning are often more expensive with an average ticket price of $759.
Cheap Chicago to Anguilla flight deals and tips
Find info about flight duration, direct flights, and airports for your flight 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?
The number of operators available for flights from Chicago to Anguilla is 1 as of June 2025.
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 | ||
|---|---|---|---|---|---|
| PriceFrom $614 | Free Cancellation | Rating 7.2 10,000 reviews |
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.