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 11/1. 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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Not ready to book? to track prices.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
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
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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
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Sat 11/7
1:55 pm-3:37 pm
Nonstop2h 42m
Chicago O'Hare Intl
Sat 11/14
10:02 am-1:24 pm
Nonstop2h 22m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Sat 11/7
1:55 pm-3:37 pm
Nonstop2h 42m
Chicago O'Hare Intl
Sat 11/14
8:05 am-3:47 pm
1 stop6h 42m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Fri 11/20
5:47 pm-10:34 pm
1 stop5h 47m
Chicago O'Hare Intl
Fri 11/27
8:05 am-2:18 pm
1 stop5h 13m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Wed 10/28
10:55 am-5:17 pm
1 stop7h 22m
Chicago O'Hare Intl
Mon 11/2
8:05 am-3:44 pm
1 stop6h 39m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Wed 10/28
12:23 pm-10:17 pm
2 stops10h 54m
Chicago O'Hare Intl
Mon 11/2
8:05 am-3:30 pm
1 stop6h 25m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Wed 10/21
4:13 pm-10:17 pm
1 stop7h 04m
Chicago O'Hare Intl
Mon 10/26
9:51 am-3:30 pm
1 stop4h 39m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Wed 10/21
12:23 pm-10:17 pm
2 stops10h 54m
Chicago O'Hare Intl
Mon 10/26
9:51 am-3:30 pm
1 stop4h 39m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Fri 4/2
3:05 pm-4:49 pm
Nonstop2h 44m
Chicago O'Hare Intl
Sat 4/10
10:50 am-2:16 pm
Nonstop2h 26m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Fri 4/2
12:00 pm-1:12 pm
1 stop26h 12m
Chicago O'Hare Intl
Sat 4/10
10:50 am-2:16 pm
Nonstop2h 26m
Hilton Head IslandChicago
HHH Hilton Head Island - ORD Chicago O'Hare Intl
HHHORD
Hilton Head Island
Sun 10/18
1:16 pm-9:42 am
1 stop21h 26m
Chicago O'Hare Intl
Thu 10/22
5:00 am-12:35 pm
1 stop6h 35m
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 $340. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $811.
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 $396 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.
What is the cheapest airline that flies from Hilton Head Island to Chicago O'Hare Intl?
Delta and United Airlines are the most popular carriers operating from Hilton Head Island to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Hilton Head Island according to our data. United Airlines is the first choice among our users, with 60% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
When to book flights from Hilton Head Island to Chicago O'Hare Intl Airport
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
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 44m.
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?
As of October 2026, there are 2 operators available to choose from 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?
Based on momondo bookings for flights between Hilton Head Island and Chicago O'Hare Intl Airport, the leading plane model is Embraer 175 (Enhanced Winglets), making up 36.21% of the total bookings. Other popular models include Embraer 175 with 32.76%, Boeing 737 with 6.90%, and Airbus A319 with 5.17%.
What is the most popular airline from Hilton Head Island to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Hilton Head Island to Chicago O'Hare Intl Airport is United Airlines (71% of total bookings). The next most popular airline is American Airlines (29%).
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 | ||
|---|---|---|---|---|---|
| PriceFrom $229 | Free Cancellation | Rating 7.4 10,315 reviews | |||
| PriceFrom $269 | Free Cancellation | Rating 7.0 12,138 reviews |
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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.