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Cheap flights from Hilton Head Island to Chicago from $249

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 9/12. 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 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 38mnonstop
American Airlines Logo
9:53 am - 1:17 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 24mnonstop
$279American Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
11:40 am - 5:42 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 02m1 stop Charlotte Douglas
American Airlines Logo
9:53 am - 1:17 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 24mnonstop
$289American Airlines
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
11:07 am - 5:28 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
7h 21m1 stop Washington, D.C. Reagan-National
American Airlines Logo
9:45 am - 1:10 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 25mnonstop
$289American Airlines
Fri, Oct 2 - Sat, Oct 3
American Airlines Logo
11:07 am - 3:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 58m1 stop Washington, D.C. Reagan-National
American Airlines Logo
6:45 am - 12:15 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
4h 30m1 stop Charlotte Douglas
$298American Airlines
Tue, Sep 22 - Tue, Sep 29
American Airlines Logo
1:52 pm - 3:30 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
2h 38mnonstop
American Airlines Logo
9:53 am - 1:17 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 24mnonstop
$299American Airlines
Tue, Aug 25 - Mon, Aug 31
American Airlines Logo
5:15 pm - 10:31 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
6h 16m1 stop Charlotte Douglas
American Airlines Logo
6:45 am - 1:50 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 05m1 stop Charlotte Douglas
$299American Airlines
Fri, Oct 2 - Sat, Oct 3
American Airlines Logo
11:07 am - 3:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
4h 58m1 stop Washington, D.C. Reagan-National
American Airlines Logo
6:45 am - 12:15 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
4h 30m1 stop Charlotte Douglas
$299American Airlines
Tue, Sep 22 - Tue, Sep 29
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
6:45 am - 2:21 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
6h 36m1 stop Charlotte Douglas
$299American Airlines
Wed, Sep 23 - Sun, Sep 27
United Airlines Logo
2:58 pm - 5:15 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 38mnonstop
$319United Airlines
Thu, Aug 27 - Mon, Aug 31
United Airlines Logo
2:48 pm - 5:05 pmHHH  Hilton Head Island-ORD Chicago O'Hare Intl
3h 17mnonstop
United Airlines Logo
10:25 am - 2:03 pmORD  Chicago O'Hare Intl-HHH Hilton Head Island
2h 38mnonstop
$359United Airlines
Sat, Sep 5 - Sun, Sep 6

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United Airlines flights from Hilton Head Island to Chicago O'Hare Intl Airport

Our best United Airlines deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets
United Airlines
Aug 17
HHH2:58 pmHilton Head Island
3h 17m
ORD5:15 pmChicago O'Hare Intl
Aug 24
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
$354
United Airlines
Aug 27
HHH2:58 pmHilton Head Island
3h 17m
ORD5:15 pmChicago O'Hare Intl
Aug 31
ORD10:25 amChicago O'Hare Intl
2h 38m
HHH2:03 pmHilton Head Island
$379
United Airlines
Sep 23
HHH2:48 pmHilton Head Island
3h 17m
ORD5:05 pmChicago O'Hare Intl
Sep 27
ORD5:00 amChicago O'Hare Intl
6h 35m
1 stop
HHH12:35 pmHilton Head Island
$394

Delta flights from Hilton Head Island to Chicago O'Hare Intl Airport

Our best Delta deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 22
HHH4:17 pmHilton Head Island
7h 01m
1 stop
ORD10:18 pmChicago O'Hare Intl
Sep 29
ORD7:05 amChicago O'Hare Intl
7h 22m
2 stops
HHH3:27 pmHilton Head Island
$304
Delta
Oct 2
HHH12:17 pmHilton Head Island
9h 13m
2 stops
ORD8:30 pmChicago O'Hare Intl
Oct 3
ORD8:05 amChicago O'Hare Intl
6h 22m
1 stop
HHH3:27 pmHilton Head Island
$324
Delta
Sep 22
HHH12:17 pmHilton Head Island
11h 01m
2 stops
ORD10:18 pmChicago O'Hare Intl
Sep 29
ORD6:00 amChicago O'Hare Intl
8h 27m
2 stops
HHH3:27 pmHilton Head Island
$330

momondo Fare Finder

 
Customize your flight search to find flights from Hilton Head Island to Chicago O'Hare Intl Airport 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 13, 2026.
Use the filters below to find and compare flights from Hilton Head Island to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

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

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 Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 9/4

11:40 am-5:42 pm

1 stop7h 02m

Chicago O'Hare Intl

Mon 9/7

9:53 am-1:17 pm

Nonstop2h 24m

$289

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/2

11:07 am-5:28 pm

1 stop7h 21m

Chicago O'Hare Intl

Sat 10/3

9:45 am-1:10 pm

Nonstop2h 25m

$289

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 9/22

11:07 am-3:05 pm

1 stop4h 58m

Chicago O'Hare Intl

Tue 9/29

6:45 am-12:15 pm

1 stop4h 30m

$298

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 8/25

1:52 pm-3:30 pm

Nonstop2h 38m

Chicago O'Hare Intl

Mon 8/31

9:53 am-1:17 pm

Nonstop2h 24m

$299

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Fri 10/2

5:15 pm-10:31 pm

1 stop6h 16m

Chicago O'Hare Intl

Sat 10/3

6:45 am-1:50 pm

1 stop6h 05m

$299

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Tue 9/22

11:07 am-3:05 pm

1 stop4h 58m

Chicago O'Hare Intl

Tue 9/29

6:45 am-12:15 pm

1 stop4h 30m

$299

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Wed 9/23

12:50 pm-5:38 pm

1 stop5h 48m

Chicago O'Hare Intl

Sun 9/27

6:45 am-2:21 pm

1 stop6h 36m

$299

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Thu 8/27

2:58 pm-5:15 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 8/31

10:25 am-2:03 pm

Nonstop2h 38m

$319

Hilton Head IslandChicago

HHH Hilton Head Island - ORD Chicago O'Hare Intl

HHHORD

Hilton Head Island

Sat 9/5

2:48 pm-5:05 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sun 9/6

10:25 am-2:03 pm

Nonstop2h 38m

$359

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Sunday is the most expensive day to depart from Hilton Head Island because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $855.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Hilton Head Island at noon is the least expensive time of day to depart. momondo users have found prices as low as $308 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $437. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Hilton Head Island to Chicago O'Hare Intl flight route?

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

What cabin class options are available on Hilton Head Island to Chicago O'Hare Intl Airport flights?

There are 2 cabin classes available to choose from on Hilton Head Island to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Hilton Head Island to Chicago O'Hare Intl Airport.

When to book flights from Hilton Head Island to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Hilton Head Island to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport (HHH to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Hilton Head Island to Chicago O'Hare Intl Airport

Best Price Found

$280

Fastest flight time

2h 38m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Hilton Head Island in the past 72 hours is $280. The best round-trip flight deal from Hilton Head Island to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $289.
The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 2h 38m
Direct flights go from Hilton Head Island to Chicago O'Hare Intl Airport on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

Frequently asked questions about flying from Hilton Head Island to Chicago O'Hare Intl Airport

  • How far is Hilton Head Island to Chicago O'Hare Intl by plane?

    The straight-line distance from Hilton Head Island to Chicago O'Hare Intl is 780.0 mi. By plane, this route typically takes 2h 38m.

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

    Prices for flights from Hilton Head Island Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Hilton Head Island Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Hilton Head Island to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Hilton Head Island to Chicago O'Hare Intl Airport?

Best airlines flying from Hilton Head Island to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Hilton Head Island to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom $229Free CancellationRating
7.4
10,111 reviews
Search United Airlines flights

  • United Airlines Flights From Hilton Head Island to Chicago O'Hare Intl Airport

    Across 6 United Airlines flights from Hilton Head Island to Chicago O'Hare Intl Airport this week, the average price was $339, with the best United Airlines deals starting from $229 round-trip. 10,111 users have rated United Airlines on momondo, with an average score of 7.4/10.

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Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Hilton Head Island to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Hilton Head Island to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Hilton Head Island.

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

Price alerts on flights to Chicago from Hilton Head Island are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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