$272 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.

Fri, Jul 17 - Mon, Jul 20
ORD
O'Hare Intl.
ANU
V.C. Bird Intl.
$990 Roundtrip, found 2 days ago
$990
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Jul 17 from O'Hare Intl. to V.C. Bird Intl., returning Mon, Jul 20, priced at $990 found 2 days ago

Airfares from $272 One Way, $546 Round Trip from Chicago to Osbourn

Prices starting at $546 for return flights and $272 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.

Wed, Nov 4 - Thu, Nov 5
ORD
Chicago
ANU
Antigua
$546 Roundtrip, found 5 days ago
$546
Roundtrip
found 5 days ago
Select Air Canada flight, departing Wed, Nov 4 from Chicago to Antigua, returning Thu, Nov 5, priced at $546 found 5 days ago
Sat, Sep 19 - Sun, Sep 27
ORD
Chicago
ANU
Antigua
$554 Roundtrip, found 5 days ago
$554
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Sep 19 from Chicago to Antigua, returning Sun, Sep 27, priced at $554 found 5 days ago
Wed, Nov 11 - Tue, Nov 17
ORD
Chicago
ANU
Antigua
$568 Roundtrip, found 4 days ago
$568
Roundtrip
found 4 days ago
Select Air Canada flight, departing Wed, Nov 11 from Chicago to Antigua, returning Tue, Nov 17, priced at $568 found 4 days ago
Tue, Aug 25 - Thu, Sep 3
ORD
Chicago
ANU
Antigua
$596 Roundtrip, found 16 hours ago
$596
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Chicago to Antigua, returning Thu, Sep 3, priced at $596 found 16 hours ago
Tue, Oct 20 - Tue, Oct 27
ORD
Chicago
ANU
Antigua
$670 Roundtrip, found 1 day ago
$670
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 20 from Chicago to Antigua, returning Tue, Oct 27, priced at $670 found 1 day ago

Osbourn economy flight packages

Price found within the past 48 hours. Click for updated prices.
Escape at Nonsuch Bay Antigua - All Inclusive - Adults Only
4.0-star property

Escape at Nonsuch Bay Antigua - All Inclusive - Adults Only

8.8/10 Excellent! (956 reviews)

Aug 20 - Aug 24

4 night stay

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

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,389, price is now $1,274 per person
$1,274
per person
found 1 day ago
I loved my stay at the Escape at Nonsuch Bay. It was peaceful, the room was clean and just as it was pictured. The atmosphere was calming and very safe. They views were breathtaking.

Reviewed on Jul 15, 2026

Galley Bay Resort & Spa
5.0-star property

Galley Bay Resort & Spa

9.4/10 Exceptional! (474 reviews)

Aug 20 - Aug 24

4 night stay

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

American Airlines • Non-stop roundtrip • Coach
Price was $4,748, price is now $2,056 per person
$2,056
per person
found 1 day ago
Galley Bay Resort is

Reviewed on Jul 15, 2026

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

The Verandah Antigua - All Inclusive - Adults Only

8.6/10 Excellent! (618 reviews)

Aug 20 - Aug 24

4 night stay

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

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,612, price is now $1,429 per person
$1,429
per person
found 1 day ago
Peace and quiet

Reviewed on Jul 14, 2026

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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.

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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.