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Cheap flights from Hilton Head Island to Chicago from $259

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Hilton Head Island to Chicago departing on 10/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Hilton Head Island to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$279American Airlines
Thu, Aug 27 - Tue, Sep 1
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
8:51 am - 12:15 pm
ORD
-
HHH
2h 24mnonstop
$279American Airlines
Fri, Aug 28 - Sat, Aug 29
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
$279United Airlines
Fri, Sep 4 - Mon, Sep 7
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
$279United Airlines
Thu, Aug 27 - Tue, Sep 1
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$279American Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$279American Airlines
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
5:16 pm - 9:57 pm
HHH
-
ORD
5h 41m
1 stop
American Airlines Logo
8:51 am - 12:15 pm
ORD
-
HHH
2h 24mnonstop
$289American Airlines
Fri, Aug 28 - Sat, Aug 29
American Airlines Logo
1:52 pm - 3:30 pm
HHH
-
ORD
2h 38mnonstop
American Airlines Logo
8:54 am - 4:38 pm
ORD
-
HHH
6h 44m
1 stop
$289American Airlines
Thu, Aug 20 - Mon, Aug 24
American Airlines Logo
3:27 pm - 9:57 pm
HHH
-
ORD
7h 30m
1 stop
American Airlines Logo
9:53 am - 1:17 pm
ORD
-
HHH
2h 24mnonstop
$289American Airlines
Fri, Sep 4 - Mon, Sep 7
United Airlines Logo
2:58 pm - 5:15 pm
HHH
-
ORD
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pm
ORD
-
HHH
2h 38mnonstop
$314United Airlines
Sun, Aug 30 - Sun, Sep 6

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United Airlines flights from Hilton Head Island to Chicago

Our best United Airlines deals on Hilton Head Island to Chicago flight tickets
United Airlines
Aug 27
HHH2:58 pmHilton Head Island
3h 17m
ORD5:15 pmChicago O'Hare Intl
Sep 1
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
$279
United Airlines
Aug 30
HHH2:58 pmHilton Head Island
3h 17m
ORD5:15 pmChicago O'Hare Intl
Sep 6
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
$314
United Airlines
Aug 7
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
Aug 14
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
$461

Delta flights from Hilton Head Island to Chicago

Our best Delta deals on Hilton Head Island to Chicago flight tickets
Delta
Aug 26
HHH12:15 pmHilton Head Island
9h 34m
2 stops
ORD8:49 pmChicago O'Hare Intl
Sep 1
ORD8:05 amChicago O'Hare Intl
6h 27m
1 stop
HHH3:32 pmHilton Head Island
$304
Delta
Aug 26
HHH12:15 pmHilton Head Island
9h 34m
2 stops
ORD8:49 pmChicago O'Hare Intl
Sep 1
ORD8:05 amChicago O'Hare Intl
6h 27m
1 stop
HHH3:32 pmHilton Head Island
$324
Delta
Aug 13
HHH12:15 pmHilton Head Island
5h 36m
1 stop
ORD4:51 pmChicago O'Hare Intl
Aug 18
ORD8:05 amChicago O'Hare Intl
6h 27m
1 stop
HHH3:32 pmHilton Head Island
$374

momondo Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 1, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/27

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Tue 9/1

9:53 am-1:17 pm

Nonstop2h 24m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/28

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Sat 8/29

8:51 am-12:15 pm

Nonstop2h 24m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 9/4

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 9/7

10:25 am-2:03 pm

Nonstop2h 38m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/27

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Tue 9/1

10:25 am-2:03 pm

Nonstop2h 38m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 9/4

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 9/7

9:53 am-1:17 pm

Nonstop2h 24m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/20

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 8/24

9:53 am-1:17 pm

Nonstop2h 24m

$279

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 8/28

5:16 pm-9:57 pm

1 stop5h 41m

Chicago O'Hare Intl

Sat 8/29

8:51 am-12:15 pm

Nonstop2h 24m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Thu 8/20

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 8/24

8:54 am-4:38 pm

1 stop6h 44m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fri 9/4

3:27 pm-9:57 pm

1 stop7h 30m

Chicago O'Hare Intl

Mon 9/7

9:53 am-1:17 pm

Nonstop2h 24m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Sun 8/30

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sun 9/6

10:25 am-2:03 pm

Nonstop2h 38m

$314

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Hilton Head Island to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $308. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Hilton Head Island to Chicago for around $855.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Hilton Head Island to Chicago during this time can be as low as $343. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $437.

What is the cheapest Hilton Head Island to Chicago flight route?

Fly from Hilton Head Island to Chicago O'Hare Intl for the best Hilton Head Island - Chicago flight prices

What cabin class options are available on Hilton Head Island to Chicago flights?

There are 2 cabin classes available to choose from on Hilton Head Island to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Hilton Head Island to Chicago flights?

No. A direct flight is the cheapest option for a flight between Hilton Head Island to Chicago.

When to book flights from Hilton Head Island to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Hilton Head Island to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Hilton Head Island to Chicago (HHH to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilton Head Island to Chicago

Best Price Found

$280

Fastest flight time

2h 46m

Direct flights

Mon, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Hilton Head Island in the past 72 hours is $280. The best round-trip flight deal from Hilton Head Island to Chicago found on momondo in the last 72 hours is $343.
The fastest flight from Hilton Head Island to Chicago takes 2h 46m
Direct flights go from Hilton Head Island to Chicago on Monday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Hilton Head Island there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Hilton Head Island to Chicago

  • How far is Hilton Head Island to Chicago by plane?

    The distance between Hilton Head Island and Chicago is about 766.4 mi. In terms of flight time, this usually takes a little over 2h 46m.

  • When did momondo last update prices for flights from Hilton Head Island Airport to Chicago?

    Prices for flights from Hilton Head Island Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Hilton Head Island Airport to Chicago?

  • How old do you have to be to fly from Hilton Head Island Airport to Chicago?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Hilton Head Island Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Hilton Head Island to Chicago?

  • What is the most popular airline from Hilton Head Island to Chicago?

Best airlines flying from Hilton Head Island to Chicago

Compare and see reviews for airlines that fly from Hilton Head Island to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $229Free CancellationRating
7.4
10,062 reviews
Search United Airlines flights

  • United Airlines Flights From Hilton Head Island to Chicago

    United Airlines flies from Hilton Head Island to Chicago around 7 times per week, with 10,062 momondo users rating the airline 7.4/10. The cheapest United Airlines deal from Hilton Head Island to Chicago in the last 72 hours was $229 (round-trip), much lower than the average airfare cost of $355 for United Airlines flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Hilton Head Island to Chicago?

It is quick and easy to find Hilton Head Island to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Hilton Head Island to Chicago with flexible booking policies on momondo?

Flights from Hilton Head Island to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Hilton Head Island to Chicago?

Once you have performed a search for Hilton Head Island to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Hilton Head Island to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Hilton Head Island to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport