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The Valley 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

The Valley and Chicago airports and terminals

Airports in The Valley , AI
map of airports in The Valley
  • 1

    Wallblake (AXA)

    Distance from City Center: 4 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 The Valley 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 $99

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 127 reviews

O'Hare International Airport Map

Rate Includes Breakfast

...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 $125

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 43 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 $127

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.7 / 5 15 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 $122

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 $169

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

Perfect for business travel and weekend getaways, the renovated Marriott Chicago Midway is just two blocks from MDW airport and offers a free 24-hr shuttle.... More

Hotel only $101

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 112 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

Flights to Chicago

Clayton J. Lloyd International Airport

If you fly from the island of Anguilla, you will pass through the Clayton J. Lloyd International Airport, previously known as Wallblake Airport. Flights from The Valley, the capital of Anguilla, are offered by Cape Air, Anguilla Air Express, and LIAT. The airport is just a few miles from The Valley, and you can get from downtown to the airport in around 15 to 20 minutes. When you need to save big on your travel arrangements, go to Orbitz.com. Orbitz provides reduced prices on air tickets and much more.

Parking at the Airport

This small airport does offer parking for those flying out of the city. When you arrive at the airport, look for the parking signs along the road. The signs will direct you to the long-term and short-stay lots.

Taxis or Shuttles

Since The Valley does not have any type of public transportation, the only way to reach the airport is by taxi or bus. Many resorts and hotels offer shuttles to the airport, and even if you do not stay at the hotel, some will let you ride the shuttle for a nominal fee. Taxis are a better choice for many, but you should book your taxi at least 24 hours before your flight. A taxi ride can cost $6 to $20, depending on your location.

Eating Before a Flight

If you need to eat before your flight, you may want to stop before you arrive at the airport. The Clayton J. Lloyd Airport only has a tiny restaurant that offers cold drinks and snacks, and it lacks any type of full-service restaurant. A small gift shop at the airport also provides some cheaper snacks for travelers. You can find several coffee shops and fast food restaurants on the roads leading to the airport. If you need to plan your trip without emptying your savings account, check with Orbitz.com before you book a flight. With cheap flights from The Valley available every day, you can book a cheaper flight whenever you need to fly.

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.