$75 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, Jun 21 - Wed, Jun 25
SAV
Savannah - Hilton Head Intl.
ORD
O'Hare Intl.
$449 Roundtrip, found 1 day ago
$449
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jun 21 from Savannah - Hilton Head Intl. to O'Hare Intl., returning Wed, Jun 25, priced at $449 found 1 day ago
Fri, Jun 20 - Tue, Aug 5
SAV
Savannah - Hilton Head Intl.
MDW
Midway Intl.
$453 Roundtrip, found 3 days ago
$453
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Jun 20 from Savannah - Hilton Head Intl. to Midway Intl., returning Tue, Aug 5, priced at $453 found 3 days ago
Fri, Jun 20 - Tue, Jun 24
HHH
Hilton Head Island
MDW
Midway Intl.
$589 Roundtrip, found 1 day ago
$589
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 20 from Hilton Head Island to Midway Intl., returning Tue, Jun 24, priced at $589 found 1 day ago

Airfares from $75 One Way, $157 Round Trip from Hilton Head Island to Chicago

Prices starting at $157 for return flights and $75 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.

Thu, Oct 23 - Wed, Oct 29
SAV
Savannah
ORD
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 23 from Savannah to Chicago, returning Wed, Oct 29, priced at $157 found 2 days ago
Thu, Oct 23 - Wed, Oct 29
SAV
Savannah
ORD
Chicago
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 23 from Savannah to Chicago, returning Wed, Oct 29, priced at $157 found 2 days ago
Thu, Oct 23 - Wed, Oct 29
SAV
Savannah
ORD
Chicago
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 23 from Savannah to Chicago, returning Wed, Oct 29, priced at $160 found 2 days ago
Thu, Oct 23 - Wed, Oct 29
SAV
Savannah
ORD
Chicago
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Oct 23 from Savannah to Chicago, returning Wed, Oct 29, priced at $197 found 2 days ago
Tue, Jul 15 - Wed, Aug 6
SAV
Savannah
MDW
Chicago
$215 Roundtrip, found 4 days ago
$215
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jul 15 from Savannah to Chicago, returning Wed, Aug 6, priced at $215 found 4 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,609 reviews)

Jul 18 - Jul 20

2 night stay

Savannah (SAV) to Chicago (ORD)

United • Coach

Chicago (ORD) to Savannah (SAV)

Southwest Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Perfect stay. Great hotel. Only complaint is the death spot in the bedroom. Gross looking stain on the floor: other than that- perfect.

Reviewed on Jun 1, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,008 reviews)

Jul 18 - Jul 20

2 night stay

Savannah (SAV) to Chicago (ORD)

United • Coach

Chicago (ORD) to Savannah (SAV)

Southwest Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (319 reviews)

Aug 7 - Aug 11

4 night stay

Savannah (SAV) to Chicago (ORD)

United • Coach

Chicago (ORD) to Savannah (SAV)

Southwest Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

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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
773 mi
Direct Flight Airlines
American Airlines, Qatar Airways, Air Canada, ANA, Air New Zealand, United Airlines
Earliest Flight Arrival
3:39PM UTC
Latest Flight Arrival
10:38PM UTC

Hilton Head Island to Chicago

Orbitz gives you great deals on your flights from Hilton Head Island to Chicago. If you also need a discount car rental or a cheap hotel room after you arrived at your destination, Orbitz has you covered.

We Offer Great Travel Deals and Discounts

When you book flights from Hilton Head Island to Chicago with Orbitz for, you can be assured that you are getting the lowest price possible. Orbitz works constantly with our airline partners to ensure guaranteed low prices on Hilton Head Island to Chicago flights for your trip—whether you are traveling for business or for fun with your family.

Enjoy Savings on Last-Minute Flights

If you are looking for a discount price on last-minute flights from Hilton Head Island to Chicago, chances are that Orbitz can offer you a deal that will save you lots of money. Whether you just want to get away for the weekend or go on a vacation lasting weeks, Orbitz can help you find the best deals on Hilton Head Island to Chicago flights that fit your budget and your itinerary for the perfect trip.

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Need more mobility when it comes to travel planning? Orbitz has easy-to-use mobile apps for iPhone, iPad, and Android, to help the traveler on the go. Not only can use the apps to find huge savings on Hilton Head Island to Chicago flights wherever you are, but you can also check out and book discount hotel rooms too. The apps will also keep you up-to-date when it’s time to fly. Get easy access to your itinerary for flights from Hilton Head Island to Chicago and review gate and baggage claim details too.

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.

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.