Find Cheap Flights from Chicago to Hilton Head (CHI - HHH)

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Tue 1/23
Tue 1/30
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Good to Know

Average Price:
$456
(avg. price over the last 2 weeks)
Good Deal:
$350
or less (round trip)

When to Book Flights from Chicago to Hilton Head

Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $349 or less.
The cheapest flight from Chicago to Hilton Head was found 79 days before departure, on average.
Book at least 6 weeks before departure in order to get a below-average price.
Morning departure is around 38% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Chicago to Hilton Head Flights

How long does a flight from Chicago to Hilton Head take?
An average nonstop flight takes 7h 49m, covering a distance of 769 miles.
Which airlines provide the cheapest flights from Chicago to Hilton Head?
In the past 3 days, the cheapest round-trip tickets were found on American Airlines ($344)
Do I need a passport to fly between Chicago and Hilton Head?
No.
What’s the cheapest day of the week to fly Chicago to Hilton Head?
For Chicago to Hilton Head, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Hilton Head back to Chicago, the best deals are generally found on Thursday, with Wednesday being the most expensive.

Book cheap flights from Chicago to Hilton Head (round-trip)

Airports
Origin
Chicago
$344
only
$344
Destination
Hilton Head
$344
only
$344
Tue, Mar 20
ORD
HHH
8h 51m
Wed, Mar 28
HHH
ORD
13h 20m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MIA
BWI
Excellent 8.6

People were nice

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

BFL
PHX
Good 7.0

Despite a departure delay due to necessity to off load some passengers due to nonfunctional seats we arrived 20 minutes early.

The seats are too narrow, which I can tolerate for about an hour.

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

Wed, Mar 21
ORD
HHH
9h 51m
Wed, Mar 28
HHH
ORD
13h 20m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

BFL
PHX
Good 7.0

Despite a departure delay due to necessity to off load some passengers due to nonfunctional seats we arrived 20 minutes early.

The seats are too narrow, which I can tolerate for about an hour.

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

Tue, Apr 24
ORD
HHH
9h 56m
Wed, May 2
HHH
ORD
9h 38m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

SDQ
MIA
Excellent 8.6

I like that it was on time

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

MIA
BWI
Excellent 8.6

People were nice

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

Wed, Apr 25
ORD
HHH
9h 56m
Wed, May 2
HHH
ORD
9h 38m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

MIA
BWI
Excellent 8.6

People were nice

SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

Sat, Apr 28
ORD
HHH
13h 47m
Mon, May 7
HHH
ORD
8h 10m
Trip: 10 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

BFL
PHX
Good 7.0

Despite a departure delay due to necessity to off load some passengers due to nonfunctional seats we arrived 20 minutes early.

The seats are too narrow, which I can tolerate for about an hour.

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

Tue, May 1
ORD
HHH
8h 56m
Wed, May 9
HHH
ORD
8h 10m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

MIA
BWI
Excellent 8.6

People were nice

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

Wed, May 2
ORD
HHH
9h 56m
Wed, May 9
HHH
ORD
8h 10m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

PVD
DCA
Excellent 10.0

Very courteous crew.pilot was amazing!! Landed in tough wind

Turbulence

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

Tue, May 8
ORD
HHH
8h 59m
Wed, May 16
HHH
ORD
8h 10m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

MIA
BWI
Excellent 8.6

People were nice

SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

Wed, May 9
ORD
HHH
8h 50m
Wed, May 16
HHH
ORD
8h 10m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

MIA
PHL
Excellent 10.0

Great fight ! The ground crew in Miami were so helpful

PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

Tue, May 15
ORD
HHH
9h 59m
Wed, May 23
HHH
ORD
8h 10m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

MIA
BWI
Excellent 8.6

People were nice

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

Sat, Feb 3
ORD
HHH
7h 51m
Sat, Feb 10
HHH
ORD
8h 28m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MIA
PHL
Excellent 10.0

Great fight ! The ground crew in Miami were so helpful

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

MIA
BWI
Excellent 8.6

People were nice

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

Tue, Apr 17
ORD
HHH
10h 26m
Wed, Apr 25
HHH
ORD
8h 49m
Trip: 9 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

PVD
DCA
Excellent 10.0

Very courteous crew.pilot was amazing!! Landed in tough wind

Turbulence

MIA
BWI
Excellent 8.6

People were nice

MIA
PHL
Excellent 10.0

Great fight ! The ground crew in Miami were so helpful

Wed, May 16
ORD
HHH
8h 20m
Wed, May 23
HHH
ORD
8h 10m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

MIA
PHL
Excellent 10.0

Great fight ! The ground crew in Miami were so helpful

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

PVD
DCA
Excellent 10.0

Very courteous crew.pilot was amazing!! Landed in tough wind

Turbulence

Tue, Mar 20
ORD
HHH
8h 51m
Mon, Mar 26
HHH
ORD
8h 57m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

Wed, Mar 21
ORD
HHH
10h 21m
Mon, Mar 26
HHH
ORD
8h 57m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PVD
DCA
Excellent 10.0

Very courteous crew.pilot was amazing!! Landed in tough wind

Turbulence

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

SDQ
MIA
Excellent 8.6

I like that it was on time

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

Thu, Mar 22
ORD
HHH
10h 21m
Wed, Mar 28
HHH
ORD
13h 20m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

SDQ
MIA
Excellent 8.6

I like that it was on time

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

MIA
PHL
Excellent 10.0

Great fight ! The ground crew in Miami were so helpful

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

Sun, Apr 15
ORD
HHH
22h 08m
Tue, Apr 24
HHH
ORD
8h 49m
Trip: 10 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

BFL
PHX
Good 7.0

Despite a departure delay due to necessity to off load some passengers due to nonfunctional seats we arrived 20 minutes early.

The seats are too narrow, which I can tolerate for about an hour.

MIA
BWI
Excellent 8.6

People were nice

PVD
DCA
Excellent 10.0

Very courteous crew.pilot was amazing!! Landed in tough wind

Turbulence

SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

Mon, Apr 16
ORD
HHH
22h 08m
Wed, Apr 25
HHH
ORD
8h 49m
Trip: 10 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
MIA
BWI
Excellent 8.6

People were nice

PVD
DCA
Excellent 10.0

Very courteous crew.pilot was amazing!! Landed in tough wind

Turbulence

PHX
PDX
Excellent 10.0

The employee who checked me in was very helpful - found my frequent flyer number for another airline and give me a free checked bag.

LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

Wed, Apr 18
ORD
HHH
7h 49m
Wed, Apr 25
HHH
ORD
11h 21m
Trip: 8 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
SFO
DFW
Excellent 10.0

Great service great entertainment to make long flight bearable

N/a

LAX
AKL
Okay 4.3

Food service was not announced. Take off was delayed one hour

LAX
YYZ
Mediocre 2.0

The layover was too short we missed our connecting flight. How did Kayak even allow us to book such an itinerary. Staff with the airline was also rude! Never will I book with site ever again!Rude

PHL
AMS
Okay 4.3

Outdated 757. No individual entertainment. Power restricted to premium seats and was intermittent when it worked.

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

Thu, Apr 19
ORD
HHH
10h 26m
Wed, Apr 25
HHH
ORD
8h 49m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 27411 reviews
Overall
7.3
Boarding
7.5
Comfort
7.1
Crew
7.8
Entertainment
6.7
Food
6.6
BFL
PHX
Good 7.0

Despite a departure delay due to necessity to off load some passengers due to nonfunctional seats we arrived 20 minutes early.

The seats are too narrow, which I can tolerate for about an hour.

MIA
PHL
Excellent 10.0

Great fight ! The ground crew in Miami were so helpful

DTW
MIA
Excellent 9.0

The professionalism of the crew and the cleanliness was excellent!

The seats weren’t very comfortable!

MIA
BWI
Excellent 8.6

People were nice

BDL
MIA
Excellent 8.6

Great light, great staff. They did not have any movies or music you could listen to, but everything else was fabulous.

Show more results

Chicago to Hilton Head Flight Information

Flights Arrive in Hilton Head
Flights Depart from Chicago
Flight Price $344
Distance 769 miles
Airlines American Airlines
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.

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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.