Cheap flight deals from Chicago (CHI) to Rockport (AUG)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Airfares from One Way, $429 Round Trip from Chicago to Rockport

Prices starting at $429 for return flights and for one-way flights to Rockport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, May 14 - Tue, May 19
ORD
Chicago
AUG
Augusta
$429 Roundtrip, found 5 days ago
$429
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, May 14 from Chicago to Augusta, returning Tue, May 19, priced at $429 found 5 days ago

Rockport economy flight packages

Price found within the past 48 hours. Click for updated prices.
Trade Winds on the Bay
3.5-star property

Trade Winds on the Bay

8.4/10 Very Good! (312 reviews)

Mar 20 - Mar 24

4 night stay

Chicago (ORD) to Rockland (RKD)

American Airlines • Roundtrip • Coach
Price was $460, price is now $376 per person
$376
per person
found 20 hours ago
The staff was friendly and helpful. The room, however, could use some updates. The shower curtain rod in the bathroom was loose and looked like it might fall, and the tub needed some fresh caulking. My main complaint is that there’s a window facing the hallway — even with the curtain closed, the light from the hallway brightens the room. I ended up using the bed sheets to block it out.

Reviewed on Nov 7, 2025

Harborline Hotel
3.0-star property

Harborline Hotel

7.6/10 Good! (218 reviews)

Mar 20 - Mar 24

4 night stay

Chicago (ORD) to Rockland (RKD)

American Airlines • Roundtrip • Coach
Price was $478, price is now $412 per person
$412
per person
found 20 hours ago
Very nice room with 2 beds, balcony, refrigerator, microwave, big cable TV and complimentary breakfast. Will stay here again.

Reviewed on Aug 18, 2025

The Country Inn at Camden Rockport
2.5-star property

The Country Inn at Camden Rockport

9.6/10 Exceptional! (1,001 reviews)

Apr 4 - Apr 6

2 night stay

Chicago (ORD) to Rockland (RKD)

Delta • Non-stop roundtrip • Coach
Price was $539, price is now $530 per person
$530
per person
found 1 day ago
The Inn is very charming and well maintained. the staff were courteous and attentive. the breakfasts were good and the cleaning staff was wonderful. The pool and hot tub were the main feature and look forward to visiting in the summer.

Reviewed on Jan 24, 2026

Don't see what you're looking for?
See all available trips from Chicago to Rockport
View all trips

More About Flying To Rockport from Chicago

Route Information for Flights from Chicago to Rockport

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

Chicago to Rockport

Using Orbitz can save you a significant amount of money and time when booking Chicago to Rockport flights. With cutting-edge mobile tools for on-the-move travel planning and guaranteed low prices, Orbitz is the ultimate resource for travelers looking for great deals.

Book Your Chicago to Rockport Flights From Any Location

Orbitz now offers free apps for iPad, iPhone, and Android users. You can use Orbitz on these devices to search for affordable fares and to book flights from Chicago to Rockport. Mobile apps also allow users to view, compare, and book hotel rooms with just a few taps on the screen and let you access up-to-date flight and baggage claim information in a matter of seconds.

Fly Cheap and Boost Your Frequent Flyer Miles

Earn miles or points on select Chicago to Rockport flights to boost your frequent flyer travel rewards. When using Orbitz to book domestic or international flights, include your frequent flyer numbers or add these details to your Orbitz user profile so they are included with your reservation.

Keep Everyone Updated With Flight Alerts

Orbitz is the ideal way to book flights from Chicago to Rockport. Free Orbitz alerts can be sent to you and as many as six of your contacts about changes to your Chicago to Rockport flights. This keeps everyone notified of flight delays or any other disruptions that might impact your arrival time.

Orbitz Makes It Easy to Plan Your Trips on a Budget

You can always find affordable flights from Chicago to Rockport on Orbitz. Use different airlines to book arrival and departure flights, take advantage of vacation package deals, and secure exclusive rewards.

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.