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Cheap flights from Chicago Midway Airport to Anguilla from $375

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 Midway Airport to Anguilla departing on 3/28. 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
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago Midway Airport to Anguilla

Cheap one-way flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
9:16 pm - 3:40 pm
MDW
-
AXA
17h 24m
3 stops
$375Multiple Airlines
Sat, Mar 28
Multiple Airlines Logo
9:16 pm - 5:10 pm
MDW
-
AXA
18h 54m
3 stops
$407Multiple Airlines
Sat, Mar 28
Multiple Airlines Logo
9:16 pm - 5:10 pm
MDW
-
AXA
18h 54m
3 stops
$422Multiple Airlines
Sat, Mar 28
Multiple Airlines Logo
9:51 pm - 3:40 pm
MDW
-
AXA
16h 49m
3 stops
$487Multiple Airlines
Fri, Mar 27
Multiple Airlines Logo
1:24 pm - 3:40 pm
MDW
-
AXA
25h 16m
3 stops
$526Multiple Airlines
Thu, Mar 26
Multiple Airlines Logo
9:51 pm - 3:40 pm
MDW
-
AXA
16h 49m
3 stops
$570Multiple Airlines
Fri, Mar 27
Multiple Airlines Logo
6:00 am - 3:24 pm
MDW
-
AXA
32h 24m
2 stops
$619Multiple Airlines
Thu, Mar 26
Multiple Airlines Logo
6:00 am - 1:30 pm
MDW
-
AXA
30h 30m
3 stops
$629Multiple Airlines
Thu, Mar 26
Multiple Airlines Logo
4:09 pm - 12:24 pm
MDW
-
AXA
19h 15m
2 stops
$638Multiple Airlines
Fri, Mar 27
Multiple Airlines Logo
4:09 pm - 12:24 pm
MDW
-
AXA
19h 15m
2 stops
$660Multiple Airlines
Fri, Mar 27

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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 March 18, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Anguilla that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest one-way

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Sat 3/28

9:16 pm-3:40 pm

3 stops17h 24m

$375

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Sat 3/28

9:16 pm-5:10 pm

3 stops18h 54m

$407

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Sat 3/28

9:16 pm-5:10 pm

3 stops18h 54m

$422
Quickest one-way

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Fri 3/27

9:51 pm-3:40 pm

3 stops16h 49m

$487

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Thu 3/26

1:24 pm-3:40 pm

3 stops25h 16m

$526

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Fri 3/27

9:51 pm-3:40 pm

3 stops16h 49m

$570

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Thu 3/26

6:00 am-3:24 pm

2 stops32h 24m

$619

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Thu 3/26

6:00 am-1:30 pm

3 stops30h 30m

$629

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Fri 3/27

4:09 pm-12:24 pm

2 stops19h 15m

$638

ChicagoThe Valley

MDW - AXA

MDWAXA

Chicago Midway

Fri 3/27

4:09 pm-12:24 pm

2 stops19h 15m

$660

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

Cheap Chicago Midway Airport to Anguilla flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Anguilla

Fastest flight time

20h 06m

Direct flights

None
The fastest flight from Chicago Midway Airport to Anguilla takes 20h 06m
There are no direct flights from Chicago Midway Airport to Anguilla. There are no popular flight routes from Chicago Midway Airport to Anguilla.
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  • When did momondo last update prices for flights from Chicago Midway Airport to Anguilla?

    Prices for flights from Chicago Midway Airport to Anguilla were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Anguilla?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport 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.

  • How do I get Price Alerts for flights from Chicago Midway Airport to Anguilla?

    Search flight deals from Chicago Midway Airport to Anguilla. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Chicago Midway Airport to Anguilla with momondo?

    By using tools like our “Price Calendar”, you can see the best day to fly round-trip for your travels. Our “Price Forecast” tool uses AI to predict whether you should purchase or hold off on booking for potentially cheaper prices. Explore shows you all flight options from a city or airport to build your own unique adventure. The Discover blog also provides valuable insights for saving money while booking your experience. After searching you can toggle on “Price Alerts” to track prices for your desired flight and book at the ideal moment.

  • How does momondo find its flight prices?

    momondo shows deals across 700+ competitors all at once. momondo is active in 30 international markets, so you can have access to a wide range of options from airlines and OTAs alike.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Anguilla?

Finding the right flight to Anguilla from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Anguilla quick and easy, saving you time and money.

Can I find flights from Chicago to Anguilla with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Anguilla from Chicago with this policy.

How can momondo help me find flights from Chicago to Anguilla?

momondo helps you find the best flight between Chicago and Anguilla by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Anguilla right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Anguilla flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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