Selected fares from Grand Cayman to Chicago

Flights from Grand Cayman

Owen Roberts International Airport

Low-cost flights from Grand Cayman Island are within your reach when you book with Orbitz.com. The Owen Roberts International Airport is the largest airport in the Cayman Islands. It is also the base of operations for Cayman Airways. The main terminal is just a couple of miles from the capital city of George Town. Cayman Airways Express operates flights between the various islands, while Delta, United Airlines, US Airways and British Airways also handle international flights. Owen Roberts International Airport also welcomes private aircraft to use their facilities.

Parking at the Airport

Both short-term and long-term parking are available at Owen Roberts International Airport. Short-term parking costs CI$2.00 per hour, while long-term rates are CI$7.00 per day. Entry to the lots is managed by computerized access systems, as are the payment terminals.

Transportation to the Airport

Several bus companies do business on Grand Cayman Island and provide transport to the airport, including an airport bus service that runs into George Town. Taxi service is available as well, and more than a dozen rental car agencies have offices in or near the airport. If you rent a car during your visit, then it's a simple matter of dropping the vehicle off and walking into the terminal when you're ready to leave.

Restaurants at Owen Roberts International Airport

The Hungry Horse Restaurant is located on the second floor of the terminal and features an open-air patio. You can also grab a snack or a cocktail at the Runaway Bar in the departure lounge. When you plan your departure with Orbitz.com, you are sure to get the premium fares for flights from Grand Cayman Island.

Flights to Chicago

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.

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Hotels in Chicago

See all 669 Hotels in Chicago
Club Quarters Hotel, Central Loop
Club Quarters Hotel, Central Loop
111 West Adams Street, Chicago
4.0 out of 5.0
4.1 out of 5 (566 reviews)

Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board ...

$130

$130
The Palmer House Hilton
The Palmer House Hilton
17 E Monroe St, Chicago
4.0 out of 5.0
4.1 out of 5 (735 reviews)

This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

$192

$192
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
20 E Chestnut St, Chicago
4.5 out of 5.0
4.6 out of 5 (140 reviews)

Located 1 block from Rush Street nightclubs, Oak Street shopping, and the Magnificent Mile, this 32-story Gold Coast hotel is 2 blocks from the John Hancock ...

$171

$171
Millennium Knickerbocker
Millennium Knickerbocker
163 East Walton Place, Chicago
4.0 out of 5.0
4.1 out of 5 (229 reviews)

This 1927 landmark Chicago hotel is a half block from Michigan Avenue/Magnificent Mile shopping, two blocks from Oak Street shopping and Water Tower Place. Lake ...

$149

$149
MileNorth Hotel
MileNorth Hotel
166 E Superior Street, Chicago
4.0 out of 5.0
4.3 out of 5 (464 reviews)

Situated in Chicago, this boutique hotel is steps from Northwestern Memorial Hospital and Chicago Water Tower. John Hancock Center and Tribune Tower are also ...

$125

$125
Hilton Chicago O'Hare Airport
Hilton Chicago O'Hare Airport
Ohare International Airport, Chicago
4.0 out of 5.0
4.0 out of 5 (157 reviews)

The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...

$164

$164
Hyatt Regency Chicago
Hyatt Regency Chicago
151 East Wacker Dr, Chicago
4.0 out of 5.0
4.1 out of 5 (755 reviews)

This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

$169

$169
Congress Plaza Hotel
Congress Plaza Hotel
520 South Michigan Avenue, Chicago
3.0 out of 5.0
3.4 out of 5 (1,245 reviews)

Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

$152

$152
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
200 North Columbus Drive, Chicago
4.5 out of 5.0
4.1 out of 5 (239 reviews)

The 45-story Fairmont Chicago hotel is adjacent to Millennium Park, a half-block from Michigan Avenue, and 3 blocks from Lake Michigan; Navy Pier, Art Institute, ...

$220

$220
Embassy Suites Chicago Downtown Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
511 North Columbus Drive, Chicago
4.0 out of 5.0
4.2 out of 5 (312 reviews)

The Embassy Suites Chicago Downtown Lakefront offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, and within ...

$209

$209

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.