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Cheap flights from Hilton Head Island to Chicago from $239

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
1:55 pm - 3:37 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 42mnonstop
American Airlines Logo
10:02 am - 1:24 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 22mnonstop
$319American Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
12:50 pm - 5:38 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
5h 48m1 stop Charlotte Douglas
American Airlines Logo
6:29 am - 2:26 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 57m1 stop Charlotte Douglas
$319American Airlines
Fri, Oct 2 - Mon, Oct 5
American Airlines Logo
12:29 pm - 5:29 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 00m1 stop Charlotte Douglas
American Airlines Logo
10:02 am - 1:24 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 22mnonstop
$329American Airlines
Sat, Dec 5 - Sat, Dec 12
Delta Logo
12:23 pm - 4:58 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
5h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:05 am - 3:30 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 25m1 stop Atlanta Hartsfield-Jackson
$339Delta
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
10:55 am - 4:15 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 20m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:00 am - 11:05 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
$339American Airlines
Wed, Oct 14 - Wed, Oct 21
American Airlines Logo
4:17 pm - 10:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 13m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 11:58 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 58m1 stop Charlotte Douglas
$339American Airlines
Sat, Dec 5 - Sat, Dec 12
American Airlines Logo
6:08 pm - 12:08 amHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 00m1 stop Charlotte Douglas
American Airlines Logo
5:00 am - 11:05 amORD  Chicago O'Hare Intl-HHH Hilton Head Island
5h 05m1 stop Charlotte Douglas
$339American Airlines
Fri, Oct 9 - Sun, Oct 11
Delta Logo
12:23 pm - 8:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
9h 07m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
8:05 am - 3:30 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 25m1 stop Atlanta Hartsfield-Jackson
$344Delta
Wed, Oct 28 - Wed, Nov 4
American Airlines Logo
1:40 pm - 3:16 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 36mnonstop
American Airlines Logo
6:29 am - 12:15 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
4h 46m1 stop Charlotte Douglas
$349American Airlines
Sat, Sep 26 - Wed, Sep 30
Delta Logo
12:23 pm - 8:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
9h 07m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
Delta Logo
6:00 am - 3:30 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
8h 30m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
$349Delta
Wed, Oct 28 - Wed, Nov 4

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Delta flights from Hilton Head Island to Chicago

Our best Delta deals on Hilton Head Island to Chicago flight tickets
Delta
Oct 28
HHH12:23 pmHilton Head Island
9h 07m
2 stops
ORD8:30 pmChicago O'Hare Intl
Nov 4
ORD8:05 amChicago O'Hare Intl
6h 25m
1 stop
HHH3:30 pmHilton Head Island
$344
Delta
Oct 2
HHH12:17 pmHilton Head Island
5h 20m
1 stop
ORD4:37 pmChicago O'Hare Intl
Oct 5
ORD6:00 amChicago O'Hare Intl
8h 27m
2 stops
HHH3:27 pmHilton Head Island
$364
Delta
Oct 2
HHH12:17 pmHilton Head Island
10h 16m
2 stops
ORD9:33 pmChicago O'Hare Intl
Oct 5
ORD6:00 amChicago O'Hare Intl
8h 27m
2 stops
HHH3:27 pmHilton Head Island
$369

American Airlines flights from Hilton Head Island to Chicago

Our best American Airlines deals on Hilton Head Island to Chicago flight tickets
American Airlines
Oct 2
HHH12:50 pmHilton Head Island
5h 48m
1 stop
ORD5:38 pmChicago O'Hare Intl
Oct 5
ORD6:29 amChicago O'Hare Intl
6h 57m
1 stop
HHH2:26 pmHilton Head Island
$319
American Airlines
Dec 5
HHH12:29 pmHilton Head Island
6h 00m
1 stop
ORD5:29 pmChicago O'Hare Intl
Dec 12
ORD10:02 amChicago O'Hare Intl
2h 22m
HHH1:24 pmHilton Head Island
$329
American Airlines
Oct 9
HHH6:08 pmHilton Head Island
7h 00m
1 stop
ORD12:08 amChicago O'Hare Intl
Oct 11
ORD5:00 amChicago O'Hare Intl
5h 05m
1 stop
HHH11:05 amHilton Head Island
$339

momondo Fare Finder

 
Use the filters below to find and compare flights from Hilton Head Island to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 12/5

1:55 pm-3:37 pm

Nonstop2h 42m

Chicago O'Hare Intl

Sat 12/12

10:02 am-1:24 pm

Nonstop2h 22m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/2

12:50 pm-5:38 pm

1 stop5h 48m

Chicago O'Hare Intl

Mon 10/5

6:29 am-2:26 pm

1 stop6h 57m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 12/5

12:29 pm-5:29 pm

1 stop6h 00m

Chicago O'Hare Intl

Sat 12/12

10:02 am-1:24 pm

Nonstop2h 22m

$329

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/28

12:23 pm-4:58 pm

1 stop5h 35m

Chicago O'Hare Intl

Wed 11/4

8:05 am-3:30 pm

1 stop6h 25m

$339

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/14

10:55 am-4:15 pm

1 stop6h 20m

Chicago O'Hare Intl

Wed 10/21

5:00 am-11:05 am

1 stop5h 05m

$339

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 12/5

4:17 pm-10:30 pm

1 stop7h 13m

Chicago O'Hare Intl

Sat 12/12

5:00 am-11:58 am

1 stop5h 58m

$339

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/9

6:08 pm-12:08 am

1 stop7h 00m

Chicago O'Hare Intl

Sun 10/11

5:00 am-11:05 am

1 stop5h 05m

$339

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/28

12:23 pm-8:30 pm

2 stops9h 07m

Chicago O'Hare Intl

Wed 11/4

8:05 am-3:30 pm

1 stop6h 25m

$344

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 9/26

1:40 pm-3:16 pm

Nonstop2h 36m

Chicago O'Hare Intl

Wed 9/30

6:29 am-12:15 pm

1 stop4h 46m

$349

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 10/28

12:23 pm-8:30 pm

2 stops9h 07m

Chicago O'Hare Intl

Wed 11/4

6:00 am-3:30 pm

2 stops8h 30m

$349

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 $340. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Hilton Head Island to Chicago for around $811.

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 $386. 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

$239

Fastest flight time

2h 42m

Direct flights

Mon and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Hilton Head Island in the past 72 hours is $239. The best round-trip flight deal from Hilton Head Island to Chicago found on momondo in the last 72 hours is $319.
The fastest flight from Hilton Head Island to Chicago takes 2h 42m
Direct flights go from Hilton Head Island to Chicago on Monday 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 42m.

  • 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
10,209 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 10,209 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?

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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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport