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Hilton Head to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Hilton Head and Chicago airports and terminals

Airports in Hilton Head SC, US
map of airports in Hilton Head
  • 1

    Hilton Head Airport (HHH)

    Distance from City Center: 3.3 miles

  • 2

    Savannah-Hilton Head (SAV)

    Distance from City Center: 26.9 miles

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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

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Cheap flights from Hilton Head to Chicago

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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 123 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 42 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 14 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $109

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 109 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

December

Lowest roundtrip airfare in December from Hilton Head to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 24 Hilton Head (HHH) Chicago (ORD) US Airways $839
Earn $8.39
Return Sat, Dec 27 Chicago (ORD) Hilton Head (HHH) US Airways
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Flights to Chicago

Hilton Head Airport Information

Use Orbitz.com to book your cheap flights from Hilton Head, and you can choose to depart from either the Hilton Head Island Airport or the Savannah/Hilton Head International Airport, located in Savannah, Georgia. The Hilton Head Island Airport is convenient, but service is limited to nine flights that depart daily from the island to Charlotte, North Carolina, and one flight on Saturday to Washington, DC. The Savannah airport is roughly 40 miles from Hilton Head, but it offers almost 40 daily flights to eight major cities on American Eagle, Delta, United and US Airways.

Parking at the Airports

The Hilton Head airport offers convenient short- and long-term parking at budget rates in lots adjacent to the terminal building. Expect to pay $9 per day in the short-term lot, and $7 per day or $42 per week in the long-term lot. The Savannah airport has several choices in parking. Both the short- and long-term lots charge $12 per day, but the long-term lot also offers a weekly rate of $60. Economy parking is also available for a daily rate of $8 or $40 per week. Book your discount tickets through Orbitz.com, and you might save enough to cover the cost of valet parking at the Savannah airport.

Ground Transportation from Hilton Head

There are several taxi companies that can get you to either airport, including Advantage Transportation, Diamond Transportation, Ferguson Transportation, Giddyup Taxi, Palmetto Taxi and Yellow Cab. Fares to the Hilton Head airport will depend on where you are coming from, but you can expect your fare to the Savannah airport to be roughly $80.

Restaurants in the Airports

Both airports have concessions where you can purchase a quick beverage or grab-and-go snack, but the Savannah airport also offers venues where you can purchase a full meal. The main terminal has a Pizza Hut, Nathans, Phillip's Famous Seafood and a Starbucks. You will find a Burger King, Starbucks, Dewar's Clubhouse Bar and Grille and Samuel Adams Toasts Savannah on the concourse. Enjoy your trip, and remember to mark your planner to check Orbitz.com the next time you need to find cheap flights from Hilton Head.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.