$256 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.

Sat, Oct 17 - Sun, Oct 18
ORD
O'Hare Intl.
ANU
V.C. Bird Intl.
$531 Roundtrip, found 6 days ago
$531
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, Oct 17 from O'Hare Intl. to V.C. Bird Intl., returning Sun, Oct 18, priced at $531 found 6 days ago

Airfares from $256 One Way, $519 Round Trip from Chicago to Osbourn

Prices starting at $519 for return flights and $256 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 13 - Tue, Nov 17
ORD
Chicago
ANU
Antigua
$519 Roundtrip, found 2 days ago
$519
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Nov 13 from Chicago to Antigua, returning Tue, Nov 17, priced at $519 found 2 days ago
Sat, Oct 17 - Sun, Oct 18
ORD
Chicago
ANU
Antigua
$531 Roundtrip, found 6 days ago
$531
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, Oct 17 from Chicago to Antigua, returning Sun, Oct 18, priced at $531 found 6 days ago
Fri, Nov 13 - Tue, Nov 17
ORD
Chicago
ANU
Antigua
$578 Roundtrip, found 2 days ago
$578
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Nov 13 from Chicago to Antigua, returning Tue, Nov 17, priced at $578 found 2 days ago
Fri, Nov 13 - Tue, Nov 17
ORD
Chicago
ANU
Antigua
$638 Roundtrip, found 2 days ago
$638
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Nov 13 from Chicago to Antigua, returning Tue, Nov 17, priced at $638 found 2 days ago
Fri, Nov 13 - Tue, Nov 17
ORD
Chicago
ANU
Antigua
$646 Roundtrip, found 2 days ago
$646
Roundtrip
found 2 days ago
Select Air Canada flight, departing Fri, Nov 13 from Chicago to Antigua, returning Tue, Nov 17, priced at $646 found 2 days ago

Osbourn economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Ocean Inn
3.0-star property

The Ocean Inn

9.2/10 Wonderful! (185 reviews)

Nov 19 - Nov 26

7 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 $1,363, price is now $1,211 per person
$1,211
per person
found 1 day ago
The staff were AMAZING - really lovely to talk to and so friendly and helpful. Couldn't fault them. The view of English Harbour/Nelson dockyard was breathtaking. So lovely to wake up to. There are works being done around the hotel but that didn't impact anything around the hotel. Everyone working was friendly too. Always greeted us. The walk to restaurants and Nelson dockyard is not bad at all. But please bear in mind there is a steep hill to the hotel, doesn't take too long (around 5-6 minutes) but cautious of when it's too hot. Breakfast is continental style, it was a little limited but that's what you would get for a smaller hotel and we went during the off-season. I think you would have an enjoyable time here.

Reviewed on Oct 13, 2026

Villa Papillon
3.5-star property

Villa Papillon

No reviews

Nov 14 - Nov 22

8 night stay

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

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $20,414, price is now $15,649 per person
$15,649
per person
found 1 day ago

Wild Lotus Villa - Waterfront on Jolly Harbour
3.5-star property

Wild Lotus Villa - Waterfront on Jolly Harbour

10/10 Exceptional! (1 review)

Nov 19 - Nov 26

7 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 $1,872, price is now $1,547 per person
$1,547
per person
found 1 day ago
Entire stay was wonderful. The manager, Jeanette was a dream- very helpful and very responsive.

Reviewed on Dec 22, 2025

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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.