$248 Cheap flight deals from Chicago (CHI) to Osbourn (ANU)

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This Weekend's Flight Deals from Chicago to Osbourn

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Apr 19 - Thu, Apr 23
ORD
O'Hare Intl.
ANU
V.C. Bird Intl.
$755 Roundtrip, found 1 day ago
$755
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, Apr 19 from O'Hare Intl. to V.C. Bird Intl., returning Thu, Apr 23, priced at $755 found 1 day ago

Airfares from $248 One Way, $504 Round Trip from Chicago to Osbourn

Prices starting at $504 for return flights and $248 for one-way flights to Osbourn were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jun 6 - Sun, Jun 14
ORD
Chicago
ANU
Antigua
$504 Roundtrip, found 17 hours ago
$504
Roundtrip
found 17 hours ago
Select Air Canada flight, departing Sat, Jun 6 from Chicago to Antigua, returning Sun, Jun 14, priced at $504 found 17 hours ago
Sat, May 30 - Sun, Jun 7
ORD
Chicago
ANU
Antigua
$512 Roundtrip, found 4 days ago
$512
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, May 30 from Chicago to Antigua, returning Sun, Jun 7, priced at $512 found 4 days ago
Sat, Jun 6 - Sun, Jun 14
ORD
Chicago
ANU
Antigua
$514 Roundtrip, found 17 hours ago
$514
Roundtrip
found 17 hours ago
Select Air Canada flight, departing Sat, Jun 6 from Chicago to Antigua, returning Sun, Jun 14, priced at $514 found 17 hours ago
Sat, May 30 - Sun, Jun 7
ORD
Chicago
ANU
Antigua
$522 Roundtrip, found 4 days ago
$522
Roundtrip
found 4 days ago
Select Air Canada flight, departing Sat, May 30 from Chicago to Antigua, returning Sun, Jun 7, priced at $522 found 4 days ago
Thu, May 28 - Sun, May 31
ORD
Chicago
ANU
Antigua
$623 Roundtrip, found 1 day ago
$623
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, May 28 from Chicago to Antigua, returning Sun, May 31, priced at $623 found 1 day ago

Osbourn economy flight packages

Price found within the past 48 hours. Click for updated prices.
Pineapple Beach Club Antigua - Adults Only – All Inclusive
4.0-star property

Pineapple Beach Club Antigua - Adults Only – All Inclusive

8.4/10 Very Good! (884 reviews)

Jun 7 - Jun 13

6 night stay

Chicago (ORD) to St. John's (ANU)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $3,523, price is now $2,103 per person
$2,103
per person
found 1 day ago
property and rooms, outdated but everything in working other. guests, older, lots of quiet retirement folk atmosphere , calm and quiet Staff, friendly and helpful Food, excellent Drinks, excellent not watered down Entertainment, lacking Beach, plenty of chairs, beautiful beach Overall, quiet, friendly, adequate resort, but not much going on at the resort. Not much to do around the resort.

Reviewed on Apr 28, 2025

The Verandah Antigua - All Inclusive - Adults Only
4.0-star property

The Verandah Antigua - All Inclusive - Adults Only

8.6/10 Excellent! (586 reviews)

May 19 - May 25

6 night stay

Chicago (MDW) to St. John's (ANU)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,382, price is now $2,245 per person
$2,245
per person
found 2 hours ago
Beautiful beach. Staff generally friendly. Forced to eat buffet everyday as other restaurants booked up well in advance. Coffee smelt like goats and didn't taste much better. Took an hour to get a pizza by the beach. Limited top shelf booze...depended on what bar you were at.

Reviewed on Feb 28, 2025

Jumby Bay Island - Oetker Collection
5.0-star property

Jumby Bay Island - Oetker Collection

10/10 Exceptional! (26 reviews)

May 19 - May 25

6 night stay

Chicago (MDW) to St. John's (ANU)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $13,012, price is now $9,239 per person
$9,239
per person
found 2 hours ago
Amazing! The best Caribbean resort in 35 years of travel.

Reviewed on Apr 22, 2017

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More About Flying To Osbourn from Chicago

Route Information for Flights from Chicago to Osbourn

Origin Airport IATA Code
CHI
Destination Airport IATA Code
ANU
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Osbourn

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Frequently asked questions

What is the shortest flight from Chicago to Osbourn?
With the trip from O'Hare Airport to ANU taking a minimum of 5 hours and 58 minutes, you'll have plenty of time to kick back and enjoy the experience. Indulge in a glass of red and settle into your seat with an interesting movie or book.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.