Search for flights
Chicago to Grand Cayman Flights
Airports in Chicago
The city of Chicago is primarily served by two international airports. Travelers looking for low-fare flights from Chicago can use Orbitz.com to find flights from both O'Hare and Midway. O'Hare International Airport is located approximately 17 miles northwest of downtown Chicago. Midway International Airport is located on the city's southwest side, approximately eight miles from Chicago's Loop. O'Hare serves as a hub for American Airlines and United Airlines, and Midway is a hub for Southwest Airlines.
Chicago Airport Parking
Daily, hourly, and valet parking are available at O'Hare. Rates vary from $2.00 to $10.00 per hour. An economy parking lot is also available at a rate of $2.00 per hour. Similar parking options and rates apply at Midway.
Chicago Airport Transportation
There are numerous transportation options for getting to and from both O'Hare and Midway. O'Hare can be accessed via regional trains, buses, and local mass transit lines. The CTA Blue Line offers a fast and convenient transportation option to and from this airport. Midway is served by the CTA Orange Line. Car rental services are available at both airports, and travelers can quickly book car rental services at either airport using Orbitz.com.
Chicago Airport Restaurants
Both O'Hare and Midway offer a variety of restaurant options for travelers. Restaurants located in both airports include Starbuck's Coffee, Chicago Style Hot Dogs, McDonald's, Auntie Anne's, Chili's, Cinnabon, and Dunkin Donuts, making it easy for visitors to grab a quick breakfast, snack, or meal. By using Orbitz.com, travelers can quickly and easily find low-fare flights from Chicago.
Owen Roberts International Airport
If you're looking for a bargain on flights to Grand Cayman Island, Orbitz.com can help you. The website searches flights from numerous airlines so that you can choose tickets that fit your budget. The Owen Roberts International Airport is the main international airport for the Cayman Islands. It's located on Grand Cayman Island-the largest of the three islands-on Roberts Drive, approximately one mile from the center of George Town. Eleven airlines service the airport, including United Airlines, Delta Air Lines, Cayman Airways and American Airlines.
Transportation From the Airport
Taxicabs are available at the airport on a first-come, first-served basis. Cab fare ranges from $12 to $70, depending on what part of Grand Cayman Island you're visiting. Cab fare into George Town averages between $15 and $18. Limousines and buses also transport passengers from the airport, but they require reservations. If you want access to your own vehicle, you can purchase a vacation package that includes car rental and flight from Orbtiz.com.
Grand Cayman Island Climate
Even though the temperatures in the Grand Cayman Islands range from the low 70s to the low 90s all year long, the weather determines the peak travel season. The off-peak travel season runs from May to November, because the islands have more rainfall during this time. If you use Orbitz.com to book your trip during the off-peak season, you'll save money on your travel expenses.
Highlights and Attractions
The Cayman Motor Museum, Dolphin Cove, Kittiwake Shipwreck & Artificial Reef and Seven Mile Beach are some of the top tourist attractions on Grand Cayman Island. In addition to finding flights to Grand Cayman Island, Orbitz.com can help you purchase tickets to local attractions and arrange guided tours.
Cheap flights from Chicago to Grand Cayman
Prices are for round-trip flights per adult (taxes and fees included)
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.
June
Cheapest weekend flights in June from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Thu, Jun 6 | Chicago (ORD) | Grand Cayman (GCM) |
|
$443 |
| Return Mon, Jun 10 | Grand Cayman (GCM) | Chicago (ORD) |
|
Lowest roundtrip airfare in June from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Sun, Jun 2 | Chicago (ORD) | Grand Cayman (GCM) |
|
$416 |
| Return Sun, Jun 9 | Grand Cayman (GCM) | Chicago (ORD) |
|
Best one-week trip in June from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Sun, Jun 2 | Chicago (ORD) | Grand Cayman (GCM) |
|
$416 |
| Return Sun, Jun 9 | Grand Cayman (GCM) | Chicago (ORD) |
|
July
Cheapest weekend flights in July from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Thu, Jul 18 | Chicago (ORD) | Grand Cayman (GCM) |
|
$524 |
| Return Mon, Jul 22 | Grand Cayman (GCM) | Chicago (ORD) |
|
Lowest roundtrip airfare in July from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Wed, Jul 24 | Chicago (ORD) | Grand Cayman (GCM) |
|
$416 |
| Return Sun, Aug 4 | Grand Cayman (GCM) | Chicago (ORD) |
|
Best one-week trip in July from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Wed, Jul 17 | Chicago (ORD) | Grand Cayman (GCM) |
|
$416 |
| Return Wed, Jul 24 | Grand Cayman (GCM) | Chicago (ORD) |
|
August
Cheapest weekend flights in August from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Thu, Aug 1 | Chicago (ORD) | Grand Cayman (GCM) |
|
$493 |
| Return Mon, Aug 5 | Grand Cayman (GCM) | Chicago (ORD) |
|
Lowest roundtrip airfare in August from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Tue, Aug 6 | Chicago (ORD) | Grand Cayman (GCM) |
|
$449 |
| Return Tue, Aug 13 | Grand Cayman (GCM) | Chicago (ORD) |
|
Best one-week trip in August from Chicago to Grand Cayman
| Travel dates | Departure | Arrival | Stops: | Round-trip |
|---|---|---|---|---|
| Leave Tue, Aug 6 | Chicago (ORD) | Grand Cayman (GCM) |
|
$449 |
| Return Tue, Aug 13 | Grand Cayman (GCM) | Chicago (ORD) |
|
Airports in Chicago IL, US
-
1
Midway Airport (MDW)
Distance from City Center: 9.5 miles
-
2
O'Hare Airport (ORD)
Distance from City Center: 15.1 miles
Airports in Grand Cayman , KY
-
1
Owen Roberts Intl (GCM)
Distance from City Center: 3.5 miles
Cheap airline tickets from Chicago to Grand Cayman
| Airline | Departure | Arrival | Travel dates | Round-trip |
|---|---|---|---|---|
|
| CHI | GCM | Wed, Jul 31 - Sun, Aug 4 | $416 |
|
| CHI | GCM | Wed, May 29 - Wed, Jun 5 | $427 |
|
| CHI | GCM | Wed, Nov 20 - Wed, Nov 27 | $430 |
|
| CHI | GCM | Sun, Jul 28 - Sun, Aug 4 | $457 |
|
| CHI | GCM | Tue, May 28 - Tue, Jun 4 | $470 |
|
| CHI | GCM | Sun, May 26 - Thu, May 30 | $773 |
|
| CHI | GCM | Fri, Dec 13 - Fri, Dec 20 | $1,070 |
|
| CHI | GCM | Tue, Sep 10 - Tue, Sep 17 | $1,979 |