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HHH - ORD

$223 Find cheap flights from Hilton Head Island to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hilton Head Island to Chicago departing on 6/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 6/2
Sun 6/9

Search hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Hilton Head Island to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 43,693,958 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Hilton Head Island to Chicago (HHH-ORD)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hilton Head Island to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:23 pm - 11:58 pmHHH-ORD
6h 35m1 stop
5:28 am - 11:40 amORD-HHH
5h 12m1 stop
$290American Airlines
Find Deal
Mon, Jul 1 - Mon, Jul 22
6:23 pm - 11:58 pmHHH-ORD
6h 35m1 stop
5:00 am - 2:11 pmORD-HHH
8h 11m2 stops
$450American Airlines
Find Deal
Mon, Jul 1 - Mon, Jul 22
11:18 am - 5:21 pmHHH-ORD
7h 03m1 stop
5:30 am - 12:26 pmORD-HHH
5h 56m1 stop
$530American Airlines
Find Deal
Thu, Oct 10 - Sun, Oct 13
4:18 pm - 9:34 pmHHH-ORD
6h 16m1 stop
5:00 am - 12:26 pmORD-HHH
6h 26m2 stops
$549American Airlines
Find Deal
Thu, Oct 10 - Sun, Oct 13
12:59 pm - 9:30 pmHHH-ORD
9h 31m2 stops
6:00 am - 4:19 pmORD-HHH
9h 19m2 stops
$569Delta
Find Deal
Mon, Jul 1 - Mon, Jul 22
11:18 am - 4:10 pmHHH-ORD
5h 52m2 stops
5:00 am - 12:26 pmORD-HHH
6h 26m2 stops
$685American Airlines
Find Deal
Thu, Oct 10 - Sun, Oct 13

Flights from Hilton Head Island to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Hilton Head Island to Chicago to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Hilton Head Island to Chicago?

The average price of all flights from Hilton Head Island to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Hilton Head Island to Chicago, look for departures on Mondays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago, Tuesday is the cheapest day to fly and Thursday is the most expensive.

Which airlines provide the cheapest flights from Hilton Head Island to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on American Airlines ($223) and Delta ($256). The cheapest round-trip tickets were found on American Airlines ($290) and Delta ($569).

Which airlines fly non-stop between Hilton Head Island and Chicago O'Hare Intl Airport?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Hilton Head Island to Chicago O'Hare Intl Airport.
There are 2 airlines that fly nonstop from Hilton Head Island to Chicago O'Hare Intl Airport. They are American Airlines and United Airlines. The cheapest airline for this route is American Airlines, with the best one-way deal found costing $195. On average, the best prices for this route can be found at American Airlines.

How many flights are there between Hilton Head Island and Chicago O'Hare Intl Airport per day?

Each day, there are 3 nonstop flights that take off from Hilton Head Island and land in Chicago O'Hare Intl Airport, with an average flight time of 2h 39m. The most common departure time is 1:00 pm and most flights take off in the afternoon. Each week, there are 3 flights and there are the same amount of flights each day 3.

Which cabin class options are there for flights between Hilton Head Island and Chicago O'Hare Intl Airport?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Hilton Head Island to Chicago?

Early birds can take the earliest flight from Hilton Head Island at 1:00 pm and will be landing in Chicago O'Hare Intl Airport at 2:44 pm.

What’s the latest departure time from Hilton Head Island to Chicago?

If you prefer to fly at night, the latest flight from Hilton Head Island to Chicago O'Hare Intl Airport jets off at 3:15 pm and lands at 4:52 pm.

Good to know

Low season

August

High season

September

Cheapest flight

$223
Best time to beat the crowds with an average 51% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from Hilton Head Island to Chicago

When to book flights from Hilton Head Island to Chicago

Are your dates flexible? Find out the best times to travel from Hilton Head Island to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hilton Head Island to Chicago flights

  • What is the cheapest flight from Hilton Head Island to Chicago O'Hare Intl Airport?

    In the last 3 days, the lowest price for a flight from Hilton Head Island to Chicago O'Hare Intl Airport was $223 for a one-way ticket and $290 for a round-trip.

  • Do I need a passport to fly between Hilton Head Island and Chicago?

    A passport is not required to fly from Hilton Head Island to Chicago.

  • Which airports will I be using when flying from Hilton Head Island to Chicago?

    On your way to Chicago, you’ll fly out from Hilton Head Island. You’ll be landing at Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Hilton Head Island to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Hilton Head Island to Chicago flight route.

  • Which airline alliances offer flights from Hilton Head Island to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Hilton Head Island and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Hilton Head Island to Chicago?

    You can catch a nonstop flight from Hilton Head Island to Chicago on Saturday.

  • How does KAYAK find such low prices on flights from Hilton Head Island to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hilton Head Island to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hilton Head Island to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hilton Head Island is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hilton Head Island to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hilton Head Island with another airline. Booking your flights between Hilton Head Island and ORD can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hilton Head Island to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hilton Head Island up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from HHH to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $278 or less one-way and $330 or less round-trip.

Prefer to fly non-stop from Hilton Head Island to Chicago?

Find which airlines fly direct from Hilton Head to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Hilton Head Island to Chicago O'Hare Intl

Saturday

American Airlines, Qatar Airways, United Airlines

American Airlines, Qatar Airways, +1 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Hilton Head Island

Saturday

American Airlines, United Airlines

American Airlines, United Airlines

See more direct flights
See more direct flights

Top airline flying from Hilton Head Island to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Hilton Head Island to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hilton Head Island to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
American AirlinesOverall score based on 14755 reviews
7.6Boarding
7.1Entertainment
6.6Food
8.0Crew
7.2Comfort
Airline reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

6.0 GoodAnonymous, Apr 2024SPI - ORD
Read more about American Airlines reviews

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Turn on the heat. Flight was way too cold from Arizona to Chicago.

Book cheap flights from Hilton Head Island to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Hilton Head Island to Chicago found on KAYAK in the last 72 hours.
6/29Sat
1 stopAmerican Airlines
10h 56mHHH-ORD
$223
5/21Tue
1 stopAmerican Airlines
4h 21mHHH-ORD
$254
5/17Fri
1 stopDelta
6h 57mHHH-ORD
$256
5/17Fri
2 stopsUnited Airlines
16h 45mHHH-ORD
$285
5/21Tue
2 stopsAmerican Airlines
9h 57mHHH-ORD
$288
5/8Wed
2 stopsUnited Airlines
16h 31mHHH-ORD
$304
5/11Sat
1 stopAmerican Airlines
6h 04mHHH-ORD
$335
5/11Sat
nonstopUnited Airlines
2h 44mHHH-ORD
$360
6/7Fri
1 stopDelta
6h 46mHHH-ORD
$410
5/8Wed
1 stopDelta
6h 57mHHH-ORD
$444

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Hilton Head Island - Chicago Flights

Departure:

Hilton Head Island (HHH)United States

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Hilton Head Island

Cabin classes:

$329

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