Cheap flights from Chicago O'Hare Intl Airport to Anguilla from $580
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 O'Hare Intl Airport to Anguilla departing on 12/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Anguilla that are best for you.
Fly from
Fly to
Route
Depart
Return
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 12/8
7:50 pm-2:54 pm
1 stop17h 04m
The Valley Wallblake Intl
Tue 12/15
3:34 pm-12:53 am
1 stop11h 19m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 12/8
7:50 pm-2:54 pm
1 stop17h 04m
The Valley Wallblake Intl
Tue 12/15
3:34 pm-12:53 am
1 stop11h 19m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 12/8
9:06 pm-2:54 pm
2 stops15h 48m
The Valley Wallblake Intl
Tue 12/15
3:34 pm-8:00 am
1 stop18h 26m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Tue 12/8
9:06 pm-2:54 pm
2 stops15h 48m
The Valley Wallblake Intl
Tue 12/15
5:39 pm-12:53 am
1 stop9h 14m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Thu 12/3
7:20 am-5:25 pm
2 stops32h 05m
The Valley Wallblake Intl
Sat 12/12
8:30 am-9:08 am
3 stops26h 38m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Thu 12/3
3:45 pm-5:25 pm
3 stops23h 40m
The Valley Wallblake Intl
Sat 12/12
12:30 pm-9:08 am
3 stops22h 38m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 1/25
7:56 pm-5:35 pm
2 stops19h 39m
The Valley Wallblake Intl
Thu 1/28
9:46 am-6:40 pm
2 stops10h 54m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 1/25
7:50 pm-5:35 pm
2 stops19h 45m
The Valley Wallblake Intl
Thu 1/28
9:46 am-7:05 pm
2 stops11h 19m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 1/25
5:10 pm-5:35 pm
2 stops22h 25m
The Valley Wallblake Intl
Thu 1/28
9:46 am-6:45 pm
1 stop10h 59m
ChicagoThe Valley
ORD Chicago O'Hare Intl - AXA The Valley Wallblake Intl
ORDAXA
Chicago O'Hare Intl
Mon 12/28
5:00 am-4:48 pm
1 stop9h 48m
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How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Anguilla
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Cheap Chicago O'Hare Intl Airport to Anguilla flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Anguilla
Frequently asked questions about flying from Chicago O'Hare Intl Airport to Anguilla
When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Anguilla?
Prices for flights from Chicago O'Hare Intl Airport to Anguilla were last updated today.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Anguilla?
There is 1 operator available for flights from Chicago O'Hare Intl Airport to Anguilla as of October 2026.
How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Anguilla.
What documentation or ID do you need to fly to Anguilla?
The necessary travel and health documents for your Anguilla trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
Best airlines flying from Chicago O'Hare Intl Airport to Anguilla
Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Anguilla with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $529 | Free Cancellation | Rating 7.0 12,128 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Anguilla?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Anguilla from Chicago.
Can I find flights from Chicago to Anguilla with flexible booking policies on momondo?
All flight searches from Chicago to Anguilla on momondo can be filtered to show those which offer flexible booking policies.
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.