$245 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, Oct 30 - Sat, Oct 31
ORD
O'Hare Intl.
ANU
V.C. Bird Intl.
$651 Roundtrip, found 4 days ago
$651
Roundtrip
found 4 days ago
Select Air Canada flight, departing Fri, Oct 30 from O'Hare Intl. to V.C. Bird Intl., returning Sat, Oct 31, priced at $651 found 4 days ago

Airfares from $245 One Way, $498 Round Trip from Chicago to Osbourn

Prices starting at $498 for return flights and $245 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.

Fri, Nov 27 - Sat, Dec 5
ORD
Chicago
ANU
Antigua
$498 Roundtrip, found 6 days ago
$498
Roundtrip
found 6 days ago
Select Air Canada flight, departing Fri, Nov 27 from Chicago to Antigua, returning Sat, Dec 5, priced at $498 found 6 days ago
Fri, Nov 27 - Sat, Dec 5
ORD
Chicago
ANU
Antigua
$508 Roundtrip, found 6 days ago
$508
Roundtrip
found 6 days ago
Select Air Canada flight, departing Fri, Nov 27 from Chicago to Antigua, returning Sat, Dec 5, priced at $508 found 6 days ago
Mon, Nov 23 - Thu, Nov 26
ORD
Chicago
ANU
Antigua
$511 Roundtrip, found 4 days ago
$511
Roundtrip
found 4 days ago
Select Air Canada flight, departing Mon, Nov 23 from Chicago to Antigua, returning Thu, Nov 26, priced at $511 found 4 days ago
Mon, Nov 16 - Tue, Nov 24
ORD
Chicago
ANU
Antigua
$518 Roundtrip, found 1 day ago
$518
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Nov 16 from Chicago to Antigua, returning Tue, Nov 24, priced at $518 found 1 day ago
Mon, Nov 16 - Tue, Nov 24
ORD
Chicago
ANU
Antigua
$528 Roundtrip, found 1 day ago
$528
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Nov 16 from Chicago to Antigua, returning Tue, Nov 24, priced at $528 found 1 day ago

Osbourn economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Verandah Antigua - All Inclusive - Adults Only
4.0-star property

The Verandah Antigua - All Inclusive - Adults Only

8.6/10 Excellent! (643 reviews)

Nov 22 - Nov 28

6 night stay

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

American Airlines • Non-stop • Coach

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

Air Canada • Non-stop • Coach
Price was $3,931, price is now $2,249 per person
$2,249
per person
found 1 day ago
The property seems dated but its well maintained. The staff is AMAZING. The grounds are BEAUTIFUL. There is a good variety of food....you won't go hungry no matter what time it is. It's a very large property but there's cart transportation thats always available. What can be improved? (1) There is no ATM on the property, we had to venture out to find one....scary (2) its an all-inclusive resort but you have to pay to have your in-room fridge stocked...why? (3) booking our scuba dive was cumbersome...they don't offer assistance at the resort and all of the diving is on the other side of the island...approx $100 in taxi fees. Still it was a wonderful vacation and we would visit again.

Reviewed on Oct 14, 2026

Galley Bay Resort & Spa - All inclusive
5.0-star property

Galley Bay Resort & Spa - All inclusive

9.4/10 Exceptional! (494 reviews)

Nov 22 - Nov 28

6 night stay

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

American Airlines • Non-stop • Coach

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

Air Canada • Non-stop • Coach
Price was $7,725, price is now $4,329 per person
$4,329
per person
found 1 day ago

Hammock Cove Antigua - All Inclusive - Adults Only
5.0-star property

Hammock Cove Antigua - All Inclusive - Adults Only

9.8/10 Exceptional! (132 reviews)

Nov 22 - Nov 28

6 night stay

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

American Airlines • Non-stop • Coach

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

Air Canada • Non-stop • Coach
Price was $8,535, price is now $5,024 per person
$5,024
per person
found 1 day ago
Me and my wife went for her birthday they set up something for her birthday was beautiful. I appreciate everything. The staff did. They treat us like Kings and Queens and I will be back thank y’all for everything.

Reviewed on Jul 30, 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.