$219 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, Mar 6 - Mon, Mar 9
ORD
O'Hare Intl.
ANU
V.C. Bird Intl.
$689 Roundtrip, found 5 days ago
$689
Roundtrip
found 5 days ago
Select Air Canada flight, departing Fri, Mar 6 from O'Hare Intl. to V.C. Bird Intl., returning Mon, Mar 9, priced at $689 found 5 days ago

Airfares from $219 One Way, $458 Round Trip from Chicago to Osbourn

Prices starting at $458 for return flights and $219 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, May 23 - Sun, May 31
ORD
Chicago
ANU
Antigua
$458 Roundtrip, found 1 day ago
$458
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, May 23 from Chicago to Antigua, returning Sun, May 31, priced at $458 found 1 day ago
Mon, Apr 20 - Tue, Apr 28
ORD
Chicago
ANU
Antigua
$470 Roundtrip, found 1 day ago
$470
Roundtrip
found 1 day ago
Select Air Canada flight, departing Mon, Apr 20 from Chicago to Antigua, returning Tue, Apr 28, priced at $470 found 1 day ago
Mon, Apr 13 - Thu, Apr 16
ORD
Chicago
ANU
Antigua
$471 Roundtrip, found 7 hours ago
$471
Roundtrip
found 7 hours ago
Select Air Canada flight, departing Mon, Apr 13 from Chicago to Antigua, returning Thu, Apr 16, priced at $471 found 7 hours ago
Fri, Apr 24 - Tue, Apr 28
ORD
Chicago
ANU
Antigua
$473 Roundtrip, found 2 days ago
$473
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Apr 24 from Chicago to Antigua, returning Tue, Apr 28, priced at $473 found 2 days ago
Mon, Apr 27 - Sun, May 3
ORD
Chicago
ANU
Antigua
$476 Roundtrip, found 4 days ago
$476
Roundtrip
found 4 days ago
Select Air Canada flight, departing Mon, Apr 27 from Chicago to Antigua, returning Sun, May 3, priced at $476 found 4 days ago

Osbourn economy flight packages

Price found within the past 48 hours. Click for updated prices.
Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only
4.5-star property

Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only

7.6/10 Good! (502 reviews)

Apr 9 - Apr 14

5 night stay

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

Delta • Non-stop • Coach

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

Air Canada • Non-stop • Coach
Price was $3,280, price is now $2,256 per person
$2,256
per person
found 1 day ago
Although the place itself is lovely it was not what I expected. I have traveled extensively at all inclusive resorts. The buffet super small compared to others. The food was only average if that. The restaurants, again average. I went because I needed to get away and relax, but the property is very loud at night with a party atmosphere. I love when a resort has entertainment, however, when you go back to your room, it shouldn’t be like you are still where the party is. The volume is so unnecessary everyone I talk to was also complaining, so I know it’s not just me. The New Year’s celebration was great and of course you expect noise then, but all the other nights the noise was over the top. All the staff are very friendly. The resort is clean. The rooms are on the small side compared to other all inclusive resorts. I could’ve paid half as much to go to one of the other resorts that I frequent but I decided I wanted to try something new.

Reviewed on Jan 6, 2026

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

The Verandah Antigua - All Inclusive - Adults Only

8.6/10 Excellent! (552 reviews)

Apr 2 - Apr 7

5 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 $3,827, price is now $2,590 per person
$2,590
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

Cocobay Resort - All Inclusive - Adults Only
4.0-star property

Cocobay Resort - All Inclusive - Adults Only

9.4/10 Exceptional! (1,001 reviews)

Apr 9 - Apr 14

5 night stay

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

Delta • Non-stop • Coach

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

Air Canada • Non-stop • Coach
Price was $4,744, price is now $3,270 per person
$3,270
per person
found 1 day ago
This place is wonderful if you’re looking for a little oasis and calm experience. I’m 32 and went on my honeymoon and had a blast. It has limited food options, but the food is pretty good. we got a pool in our cottage which is a must based on the limited options. The views are amazing. If you’re looking for relaxation and time with your person, this place is simply wonderful! Definitely do one of the floating meals as well!

Reviewed on Jul 22, 2023

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Osbourn first class flight packages

Price found within the past 48 hours. Click for updated prices.
St. James's Club Antigua - All Inclusive
4.0-star property

St. James's Club Antigua - All Inclusive

8.4/10 Very Good! (766 reviews)

Apr 13 - Apr 19

6 night stay

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

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $4,514, price is now $2,718 per person
$2,718
per person
found 21 hours ago
The damn frogs were beefin all night sounding like they were chilling in a rocking chair all night. Seaweed smell was cray in the mornings. BUT really enjoyed the spa, snorkeling excursion and friendliness of the staff. Oh and the coffee shop was a great perk.

Reviewed on Jun 27, 2024

Cocobay Resort - All Inclusive - Adults Only
4.0-star property

Cocobay Resort - All Inclusive - Adults Only

9.4/10 Exceptional! (1,001 reviews)

Apr 13 - Apr 19

6 night stay

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

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
Price was $5,905, price is now $4,272 per person
$4,272
per person
found 21 hours ago
This place is wonderful if you’re looking for a little oasis and calm experience. I’m 32 and went on my honeymoon and had a blast. It has limited food options, but the food is pretty good. we got a pool in our cottage which is a must based on the limited options. The views are amazing. If you’re looking for relaxation and time with your person, this place is simply wonderful! Definitely do one of the floating meals as well!

Reviewed on Jul 22, 2023

Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only
4.5-star property

Royalton CHIC Antigua, An Autograph Collection All-Inclusive Resort – Adults Only

7.6/10 Good! (502 reviews)

Apr 13 - Apr 19

6 night stay

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

American Airlines • Non-stop roundtrip • FirstClass
Price was $4,511, price is now $3,275 per person
$3,275
per person
found 21 hours ago
Although the place itself is lovely it was not what I expected. I have traveled extensively at all inclusive resorts. The buffet super small compared to others. The food was only average if that. The restaurants, again average. I went because I needed to get away and relax, but the property is very loud at night with a party atmosphere. I love when a resort has entertainment, however, when you go back to your room, it shouldn’t be like you are still where the party is. The volume is so unnecessary everyone I talk to was also complaining, so I know it’s not just me. The New Year’s celebration was great and of course you expect noise then, but all the other nights the noise was over the top. All the staff are very friendly. The resort is clean. The rooms are on the small side compared to other all inclusive resorts. I could’ve paid half as much to go to one of the other resorts that I frequent but I decided I wanted to try something new.

Reviewed on Jan 6, 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.