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Cheap flights from Hilton Head Island to Chicago from $177

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 5/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Hilton Head Island to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:05 pm - 10:36 pm
HHH
-
ORD
7h 31m
1 stop
Delta Logo
7:10 am - 3:18 pm
ORD
-
HHH
7h 08m
1 stop
$223Delta
Mi, Jun 3 - Mo, Jun 8
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
$229United Airlines
Mi, Jun 3 - Mo, Jun 8
United Airlines Logo
3:05 pm - 4:51 pm
HHH
-
ORD
2h 46mnonstop
United Airlines Logo
10:45 am - 2:21 pm
ORD
-
HHH
2h 36mnonstop
$274United Airlines
Mi, Jul 1 - Mi, Jul 8
United Airlines Logo
3:05 pm - 4:49 pm
HHH
-
ORD
2h 44mnonstop
United Airlines Logo
10:50 am - 2:16 pm
ORD
-
HHH
2h 26mnonstop
$280United Airlines
Do, Apr 9 - Mo, Apr 13
Delta Logo
12:07 pm - 6:35 pm
HHH
-
ORD
7h 28m
1 stop
Delta Logo
7:07 am - 3:22 pm
ORD
-
HHH
7h 15m
1 stop
$294Delta
Fr, Mai 8 - Di, Mai 12
United Airlines Logo
3:08 pm - 4:49 pm
HHH
-
ORD
2h 41mnonstop
United Airlines Logo
10:45 am - 2:11 pm
ORD
-
HHH
2h 26mnonstop
$295United Airlines
Mi, Mai 13 - Mi, Mai 20
United Airlines Logo
3:00 pm - 4:44 pm
HHH
-
ORD
2h 44mnonstop
United Airlines Logo
10:50 am - 2:16 pm
ORD
-
HHH
2h 26mnonstop
$301United Airlines
Mo, Mrz 30 - Mo, Apr 6
Delta Logo
4:00 pm - 8:45 pm
HHH
-
ORD
5h 45m
1 stop
Delta Logo
9:30 am - 3:18 pm
ORD
-
HHH
4h 48m
1 stop
$308Delta
Mi, Jul 1 - Mi, Jul 8
United Airlines Logo
3:08 pm - 4:49 pm
HHH
-
ORD
2h 41mnonstop
United Airlines Logo
10:45 am - 2:11 pm
ORD
-
HHH
2h 26mnonstop
$319United Airlines
Fr, Mai 1 - So, Mai 3
Delta Logo
12:07 pm - 6:35 pm
HHH
-
ORD
7h 28m
1 stop
Delta Logo
6:00 am - 3:22 pm
ORD
-
HHH
8h 22m
2 stops
$324Delta
Fr, Mai 8 - Di, Mai 12

American Airlines flights from Hilton Head Island to Chicago

Our best American Airlines deals on Hilton Head Island to Chicago flight tickets
American Airlines
Jul 1
HHH2:03 pmHilton Head Island
2h 35m
ORD3:38 pmChicago O'Hare Intl
Jul 8
ORD8:50 amChicago O'Hare Intl
6h 35m
1 stop
HHH4:25 pmHilton Head Island
$339
American Airlines
Jun 3
HHH2:05 pmHilton Head Island
2h 35m
ORD3:40 pmChicago O'Hare Intl
Jun 8
ORD10:06 amChicago O'Hare Intl
2h 29m
HHH1:35 pmHilton Head Island
$356
American Airlines
Jun 3
HHH2:05 pmHilton Head Island
2h 35m
ORD3:40 pmChicago O'Hare Intl
Jun 8
ORD7:58 amChicago O'Hare Intl
5h 15m
1 stop
HHH2:13 pmHilton Head Island
$366

United Airlines flights from Hilton Head Island to Chicago

Our best United Airlines deals on Hilton Head Island to Chicago flight tickets
United Airlines
Jun 3
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
Jun 8
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
$229
United Airlines
Jul 1
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
Jul 8
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
$274
United Airlines
Apr 9
HHH3:05 pmHilton Head Island
2h 44m
ORD4:49 pmChicago O'Hare Intl
Apr 13
ORD10:50 amChicago O'Hare Intl
2h 26m
HHH2:16 pmHilton Head Island
$280

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 März 11, 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

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mi 6/3

4:05 pm-10:36 pm

1 stop7h 31m

Chicago O'Hare Intl

Mo 6/8

7:10 am-3:18 pm

1 stop7h 08m

$223

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mi 6/3

3:05 pm-4:51 pm

Nonstop2h 46m

Chicago O'Hare Intl

Mo 6/8

10:45 am-2:21 pm

Nonstop2h 36m

$229

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mi 7/1

3:05 pm-4:51 pm

Nonstop2h 46m

Chicago O'Hare Intl

Mi 7/8

10:45 am-2:21 pm

Nonstop2h 36m

$274

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Do 4/9

3:05 pm-4:49 pm

Nonstop2h 44m

Chicago O'Hare Intl

Mo 4/13

10:50 am-2:16 pm

Nonstop2h 26m

$280

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fr 5/8

12:07 pm-6:35 pm

1 stop7h 28m

Chicago O'Hare Intl

Di 5/12

7:07 am-3:22 pm

1 stop7h 15m

$294
Quickest round-trip

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mi 5/13

3:08 pm-4:49 pm

Nonstop2h 41m

Chicago O'Hare Intl

Mi 5/20

10:45 am-2:11 pm

Nonstop2h 26m

$295

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mo 3/30

3:00 pm-4:44 pm

Nonstop2h 44m

Chicago O'Hare Intl

Mo 4/6

10:50 am-2:16 pm

Nonstop2h 26m

$301

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Mi 7/1

4:00 pm-8:45 pm

1 stop5h 45m

Chicago O'Hare Intl

Mi 7/8

9:30 am-3:18 pm

1 stop4h 48m

$308

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fr 5/1

3:08 pm-4:49 pm

Nonstop2h 41m

Chicago O'Hare Intl

So 5/3

10:45 am-2:11 pm

Nonstop2h 26m

$319

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

Fr 5/8

12:07 pm-6:35 pm

1 stop7h 28m

Chicago O'Hare Intl

Di 5/12

6:00 am-3:22 pm

2 stops8h 22m

$324

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 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

$234

Fastest flight time

2h 41m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Hilton Head Island in the past 72 hours is $234. The best round-trip flight deal from Hilton Head Island to Chicago found on momondo in the last 72 hours is $359.
The fastest flight from Hilton Head Island to Chicago takes 2h 41m
Direct flights go from Hilton Head Island to Chicago every day.
There are 3 airports in Chicago. From Hilton Head Island there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • 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 41m.

  • 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 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?

Traveling to a place near Chicago?

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