$119 Cheap flight deals from Hilton Head Island (SAV) to Chicago (CHI)

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This Weekend's Flight Deals from Hilton Head Island to Chicago

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, Mar 14 - Tue, Mar 31
SAV
Savannah - Hilton Head Intl.
ORD
O'Hare Intl.
$475 Roundtrip, found 21 hours ago
$475
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Sat, Mar 14 from Savannah - Hilton Head Intl. to O'Hare Intl., returning Tue, Mar 31, priced at $475 found 21 hours ago
Sun, Mar 15 - Wed, Mar 18
SAV
Savannah - Hilton Head Intl.
RFD
Greater Rockford
$655 Roundtrip, found 6 days ago
$655
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sun, Mar 15 from Savannah - Hilton Head Intl. to Greater Rockford, returning Wed, Mar 18, priced at $655 found 6 days ago
Sun, Mar 15 - Sun, Mar 29
SAV
Savannah - Hilton Head Intl.
MDW
Midway Intl.
$753 Roundtrip, found 22 hours ago
$753
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sun, Mar 15 from Savannah - Hilton Head Intl. to Midway Intl., returning Sun, Mar 29, priced at $753 found 22 hours ago

Airfares from $119 One Way, $248 Round Trip from Hilton Head Island to Chicago

Prices starting at $248 for return flights and $119 for one-way flights to Chicago 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, Apr 15 - Wed, May 13
HHH
Hilton Head Island
ORD
Chicago
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Wed, May 13, priced at $248 found 1 day ago
Wed, Apr 15 - Wed, May 13
HHH
Hilton Head Island
ORD
Chicago
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select United flight, departing Wed, Apr 15 from Hilton Head Island to Chicago, returning Wed, May 13, priced at $255 found 1 day ago
Tue, Aug 11 - Tue, Aug 25
HHH
Hilton Head Island
ORD
Chicago
$269 Roundtrip, found 23 hours ago
$269
Roundtrip
found 23 hours ago
Select Delta flight, departing Tue, Aug 11 from Hilton Head Island to Chicago, returning Tue, Aug 25, priced at $269 found 23 hours ago
Wed, Apr 15 - Sun, Apr 19
SAV
Savannah
ORD
Chicago
$293 Roundtrip, found 5 days ago
$293
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Apr 15 from Savannah to Chicago, returning Sun, Apr 19, priced at $293 found 5 days ago
Fri, Apr 17 - Sun, Apr 19
SAV
Savannah
ORD
Chicago
$297 Roundtrip, found 19 hours ago
$297
Roundtrip
found 19 hours ago
Select Sun Country Airlines flight, departing Fri, Apr 17 from Savannah to Chicago, returning Sun, Apr 19, priced at $297 found 19 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.4/10 Very Good! (2,220 reviews)

Apr 17 - Apr 19

2 night stay

Savannah (SAV) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Savannah (SAV)

Sun Country Airlines • Non-stop • Coach
Price was $688, price is now $569 per person
$569
per person
found 6 hours ago
This place gets 3 stars from me only due to its great location. It's in rather poor repair and its overall appearance and upkeep do not reflect well on the Hilton brand. It seems clear that property ownership are not bothering to put money into it because they know they will get traffic from the airport.

Reviewed on Feb 25, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,438 reviews)

Apr 17 - Apr 19

2 night stay

Savannah (SAV) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Savannah (SAV)

Sun Country Airlines • Non-stop • Coach
Price was $840, price is now $613 per person
$613
per person
found 6 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

9/10 Wonderful! (3,285 reviews)

Apr 17 - Apr 19

2 night stay

Savannah (SAV) to Chicago (ORD)

American Airlines • Non-stop • Coach

Chicago (ORD) to Savannah (SAV)

Sun Country Airlines • Non-stop • Coach
Price was $692, price is now $578 per person
$578
per person
found 6 hours ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

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More About Flying To Chicago from Hilton Head Island

Route Information for Flights from Hilton Head Island to Chicago

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

Hilton Head Island to Chicago

Looking for cheap Hilton Head Island to Chicago flights? Orbitz has the cheapest air fares for flights from Hilton Head Island to Chicago. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

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Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Hilton Head Island to Chicago flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Hilton Head Island to Chicago on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Hilton Head Island to Chicago flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Chicago. Need hotels too? You can book them last minute on your mobile phone.

Frequently asked questions

Are there non-stop flights from Hilton Head Island to Chicago?
Yes, you'll be pleased to hear that you can jet straight from Savannah - Hilton Head Intl. Airport (SAV) to O'Hare Intl. Airport (ORD). Direct flights can be booked with United Airlines and American Airlines.
What is the shortest flight from Hilton Head Island to Chicago?
If conditions are good and there are no unexpected hiccups, you could be stepping off the plane at MDW from SAV in only 2 hours and 46 minutes. With such a quick flight time, consider taking carry-on luggage only.
What airlines fly from Hilton Head Island to Chicago most frequently?
There are two airlines offering frequent flights from Savannah - Hilton Head Intl. Airport (SAV) to ORD, including United Airlines (UA). The preferred choice of many travelers, it operates 91 flights on this route each month. Also consider the deals available with American Airlines (AA). Offering 30 flights every month between Hilton Head Island and Chicago, they'll ensure your journey is just as good as the destination.
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.