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Cheap flights from Hilton Head Island to Chicago from $148

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 5/19. 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
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.
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
$269United Airlines
tir., maj 12 - søn., maj 17
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
$289Delta
tir., maj 12 - ons., maj 20
Delta Logo
12:18 pm - 8:14 pm
HHH
-
ORD
8h 56m
2 stops
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
$294Delta
tor., maj 14 - tir., maj 26
Delta Logo
12:18 pm - 8:14 pm
HHH
-
ORD
8h 56m
2 stops
Delta Logo
7:00 am - 3:33 pm
ORD
-
HHH
7h 33m
2 stops
$300Delta
ons., maj 13 - tir., maj 26
Delta Logo
12:11 pm - 6:42 pm
HHH
-
ORD
7h 31m
1 stop
Delta Logo
8:03 am - 3:29 pm
ORD
-
HHH
6h 26m
1 stop
$309Delta
fre., juli 3 - tor., juli 9
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
$330United Airlines
tir., maj 5 - lør., maj 9
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
$334United Airlines
tor., maj 21 - tor., maj 28
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
Delta Logo
7:07 am - 3:33 pm
ORD
-
HHH
7h 26m
1 stop
$344Delta
tir., maj 12 - søn., maj 17
Delta Logo
4:16 pm - 10:36 pm
HHH
-
ORD
7h 20m
1 stop
Delta Logo
7:00 am - 3:33 pm
ORD
-
HHH
7h 33m
2 stops
$349Delta
tir., maj 12 - man., maj 25
Delta Logo
12:18 pm - 8:14 pm
HHH
-
ORD
8h 56m
2 stops
Delta Logo
7:00 am - 3:33 pm
ORD
-
HHH
7h 33m
2 stops
$354Delta
ons., maj 13 - søn., maj 24

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

Our best American Airlines deals on Hilton Head Island to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jun 10
HHH2:04 pmHilton Head Island
2h 33m
ORD3:37 pmChicago O'Hare Intl
Jun 13
ORD5:00 amChicago O'Hare Intl
5h 10m
1 stop
HHH11:10 amHilton Head Island
$389
American Airlines
Jun 10
HHH2:43 pmHilton Head Island
6h 02m
1 stop
ORD7:45 pmChicago O'Hare Intl
Jun 13
ORD5:00 amChicago O'Hare Intl
5h 10m
1 stop
HHH11:10 amHilton Head Island
$399
American Airlines
Jun 16
HHH11:40 amHilton Head Island
5h 19m
1 stop
ORD3:59 pmChicago O'Hare Intl
Jun 20
ORD10:16 amChicago O'Hare Intl
2h 30m
HHH1:46 pmHilton Head Island
$406

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
May 12
HHH3:08 pmHilton Head Island
2h 41m
ORD4:49 pmChicago O'Hare Intl
May 17
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
$269
United Airlines
May 5
HHH3:08 pmHilton Head Island
2h 41m
ORD4:49 pmChicago O'Hare Intl
May 9
ORD10:45 amChicago O'Hare Intl
2h 26m
HHH2:11 pmHilton Head Island
$330
United Airlines
May 21
HHH3:05 pmHilton Head Island
2h 46m
ORD4:51 pmChicago O'Hare Intl
May 28
ORD10:45 amChicago O'Hare Intl
2h 36m
HHH2:21 pmHilton Head Island
$334

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 april 23, 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 - ORD

HHHORD

Hilton Head Island

tir. 5/12

3:08 pm-4:49 pm

Nonstop2h 41m

Chicago O'Hare Intl

søn. 5/17

10:45 am-2:11 pm

Nonstop2h 26m

$269

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

tir. 5/12

4:16 pm-10:36 pm

1 stop7h 20m

Chicago O'Hare Intl

ons. 5/20

7:07 am-3:33 pm

1 stop7h 26m

$289

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

tor. 5/14

12:18 pm-8:14 pm

2 stops8h 56m

Chicago O'Hare Intl

tir. 5/26

7:07 am-3:33 pm

1 stop7h 26m

$294

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

ons. 5/13

12:18 pm-8:14 pm

2 stops8h 56m

Chicago O'Hare Intl

tir. 5/26

7:00 am-3:33 pm

2 stops7h 33m

$300

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

fre. 7/3

12:11 pm-6:42 pm

1 stop7h 31m

Chicago O'Hare Intl

tor. 7/9

8:03 am-3:29 pm

1 stop6h 26m

$309

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

tir. 5/5

3:08 pm-4:49 pm

Nonstop2h 41m

Chicago O'Hare Intl

lør. 5/9

10:45 am-2:11 pm

Nonstop2h 26m

$330

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

tor. 5/21

3:05 pm-4:51 pm

Nonstop2h 46m

Chicago O'Hare Intl

tor. 5/28

10:45 am-2:21 pm

Nonstop2h 36m

$334

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

tir. 5/12

4:16 pm-10:36 pm

1 stop7h 20m

Chicago O'Hare Intl

søn. 5/17

7:07 am-3:33 pm

1 stop7h 26m

$344

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

tir. 5/12

4:16 pm-10:36 pm

1 stop7h 20m

Chicago O'Hare Intl

man. 5/25

7:00 am-3:33 pm

2 stops7h 33m

$349

Hilton Head IslandChicago

HHH - ORD

HHHORD

Hilton Head Island

ons. 5/13

12:18 pm-8:14 pm

2 stops8h 56m

Chicago O'Hare Intl

søn. 5/24

7:00 am-3:33 pm

2 stops7h 33m

$354

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 Thursday when prices can be found for as low as $355. 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 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 3 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

$213

Fastest flight time

2h 41m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Hilton Head Island in the past 72 hours is $213. 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 $339.
The fastest flight from Hilton Head Island to Chicago O'Hare Intl Airport takes 2h 41m
Direct flights go from Hilton Head Island to Chicago O'Hare Intl Airport every day.
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 41m.

  • 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 $223Free CancellationRating
7.4
9,637 reviews
Search United Airlines flights

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

    Across 7 United Airlines flights from Hilton Head Island to Chicago O'Hare Intl Airport this week, the average price was $355, with the best United Airlines deals starting from $223 round-trip. 9,637 users have rated United Airlines on momondo, with an average score of 7.4/10.

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?

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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