Cheap flights from Grand Cayman to Chicago
Flights overview
Prices shown are for one adult in Economy class flights from Zürich to New York. This includes the cheapest Business class options where available.
Prices reflect the lowest available in the next three months, though they are subject to change and availability.
Last-minute deals apply to the cheapest weekend trips available in the next seven days, with weekend trips being flights departing between Thursday and Saturday and returning on Sunday or Monday.
Flight duration shown is based on nonstop flights or those with the fewest stops available.
Prices reflect the lowest available in the next three months, though they are subject to change and availability.
Last-minute deals apply to the cheapest weekend trips available in the next seven days, with weekend trips being flights departing between Thursday and Saturday and returning on Sunday or Monday.
Flight duration shown is based on nonstop flights or those with the fewest stops available.
Useful information for finding cheap flights from Grand Cayman to Chicago and booking your next trip
| Cheapest round-trip flights | $366 |
Air Canada
1 stop
21 hr
Thu, Jun 11 — Wed, Jun 17
|
The cheapest round-trip flight from Grand Cayman to Chicago is currently $366 | |
|---|---|---|---|---|
| Cheapest one-way flight | $233 |
Air Canada
1 stop
25 hr
Thu, Jun 11
|
The cheapest one-way flight from Grand Cayman to Chicago is currently $233 | |
| Cheapest nonstop flights | $651 |
United
Nonstop
5 hr
Sat, May 16 — Sat, May 23
|
The cheapest nonstop round-trip flight from Grand Cayman to Chicago is currently $651 | |
| Last-minute weekend getaway | $315 |
United
1 stop
18 hr
Sat, Apr 25 — Sun, Apr 26
|
The cheapest last-minute weekend getaway from Grand Cayman to Chicago is currently $315 | |
| Cheapest business class flights | $1,125 |
American
1 stop
16 hr
Fri, Jul 17 — Sun, Jul 26
|
The cheapest business class round-trip flight from Grand Cayman to Chicago is currently $1,125 | |
| Fastest flight | 4 hr 23 min | The fastest nonstop flight from Grand Cayman to Chicago takes 4 hr 23 min |
|---|---|---|
| Nonstop flights | Some days | There are direct flights on this route 4 days a week: Mon, Tue, Wed, Sat. |
When is the cheapest time to fly?
Typical prices for the least expensive flights for 1-week trips from Grand Cayman to Chicago per month. Insights are based on fares observed in the last 12 months. Current prices may differ.
The cheapest month to fly from Grand Cayman to Chicago is typically January. The most expensive month to fly is typically June.
| January Cheapest
|
Typical prices: $290–620 |
|---|---|
| June Most expensive
|
Typical prices: $570–740 |
Popular airlines from Grand Cayman to Chicago
Popularity is based on the number of weekly nonstop and connecting flights the airline operates. Connecting flights do not include interline routes.
Flight suggestions are based on an airline's cheapest round-trip fares from Grand Cayman to Chicago in the next 3 months. Prices include required taxes + fees for one adult. Optional charges and bag fees may apply.
Typical prices are based on fares observed in the past year for one-week round trips with the same origin, destination, and airline.
- Southwestfrom $579Typical price: $530–960728 weekly connecting flightsGCM - MDW, ORD Every day
- UnitedNonstopfrom $631Typical price: $470–9007 weekly nonstop flightsGCM - ORD Every day98 weekly connecting flightsGCM - ORD Every day
- Americanfrom $606Typical price: $465–840331 weekly connecting flightsGCM - ORD Every day
- Deltafrom $472Typical price: $520–1,250167 weekly connecting flightsGCM - MDW, ORD Every day
- JetBlueTypical price: $490–1,6509 weekly connecting flightsGCM - ORD Every day
- Air Canadafrom $366Typical price: $460–1,7507 weekly connecting flightsGCM - ORD Every Mon, Thu, Fri, Sun
Popular airports near Grand Cayman
Distance and driving time are relative to the city center. Airports are listed based on distance from Grand Cayman center and popularity with travelers.
- Owen Roberts International Airport (GCM)Grand Cayman Cayman Islands 24 min 7 mi
Popular airports near Chicago
Distance and driving time are relative to the city center. Airports are listed based on distance from Chicago center and popularity with travelers.
- Chicago O'Hare International Airport (ORD)Chicago United States 26 min 16 mi
- Chicago Midway International Airport (MDW)Chicago United States 25 min 9 mi
- Milwaukee Mitchell International Airport (MKE)Milwaukee United States 1 hr 23 min 75 mi
- Indianapolis International Airport (IND)Indianapolis United States 2 hr 58 min 165 mi
Frequently asked questions about flying from Grand Cayman to Chicago
The cheapest flights from Grand Cayman to Chicago are usually in January. Typical ticket prices in January range from $290 to $620.
The cheapest round-trip flight from Grand Cayman to Chicago recently found on Google Flights was with Air Canada from $366. The cheapest one-way flight was with Air Canada from $233.
Some of the cheapest round-trip deals we found with different airlines:
Some of the cheapest round-trip deals we found with different airlines:
- The cheapest Southwest flight from Grand Cayman to Chicago is $579, flying from May 28 to Jun 3.
- The cheapest United flight from Grand Cayman to Chicago is $631, flying from Jul 18 to Jul 26.
- The cheapest American flight from Grand Cayman to Chicago is $606, flying from May 28 to Jun 6.
- The cheapest Delta flight from Grand Cayman to Chicago is $472, flying from Jul 16 to Jul 22.
- The cheapest Air Canada flight from Grand Cayman to Chicago is $366, flying from Jun 11 to Jun 17.
The cheapest round-trip flight from Grand Cayman to Chicago starts at $366 from Thu, Jun 11 to Wed, Jun 17. The cheapest one-way flight starts at $233 and departs on Thu, Jun 11.
4 hr 23 min is the shortest flight time from Grand Cayman to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Grand Cayman to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.
You can also turn on price tracking to get alerts if the price changes for a route or flight.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.
You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Grand Cayman to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Grand Cayman to Chicago.
In terms of nonstop flights, United is the most popular. United offers 7 nonstop flights and 98 connecting flights per week. United flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
In terms of flights, Southwest is the most popular. Southwest offers 728 connecting flights per week. Southwest flies from Owen Roberts International Airport (GCM) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
Other popular airlines flying from Grand Cayman to Chicago are:
In terms of nonstop flights, United is the most popular. United offers 7 nonstop flights and 98 connecting flights per week. United flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
In terms of flights, Southwest is the most popular. Southwest offers 728 connecting flights per week. Southwest flies from Owen Roberts International Airport (GCM) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
Other popular airlines flying from Grand Cayman to Chicago are:
- American offers 331 connecting flights per week. American flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
- Delta offers 167 connecting flights per week. Delta flies from Owen Roberts International Airport (GCM) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
- JetBlue offers 9 connecting flights per week. JetBlue flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
- Air Canada offers 7 connecting flights per week. Air Canada flies from Owen Roberts International Airport (GCM) to Chicago O'Hare International Airport (ORD) .
The cheapest round-trip flight from Grand Cayman to Chicago recently found on Google Flights was with Air Canada from $366. The cheapest one-way flight was with Air Canada from $233.
Some of the cheapest round-trip deals we found with different airlines:
Some of the cheapest round-trip deals we found with different airlines:
- The cheapest Southwest flight from Grand Cayman to Chicago is $579, flying from May 28 to Jun 3.
- The cheapest United flight from Grand Cayman to Chicago is $631, flying from Jul 18 to Jul 26.
- The cheapest American flight from Grand Cayman to Chicago is $606, flying from May 28 to Jun 6.
- The cheapest Delta flight from Grand Cayman to Chicago is $472, flying from Jul 16 to Jul 22.
- The cheapest Air Canada flight from Grand Cayman to Chicago is $366, flying from Jun 11 to Jun 17.
United flies direct from Grand Cayman to Chicago.
- There are 7 United direct flights from Grand Cayman to Chicago per week. Flights are available every day.
The cheapest last-minute deal between Grand Cayman and Chicago at price $315 is offered by United from Sat, Apr 25 to Sun, Apr 26.
United flies direct from Grand Cayman to Chicago.
- There are 7 United direct flights from Grand Cayman to Chicago per week. Flights are available every day.
Direct flights from Grand Cayman to Chicago are only available on Monday, Tuesday, Wednesday and Saturday.
The cheapest direct (nonstop) round-trip flights between Grand Cayman and Chicago start at $651 from Sat, May 16 to Sat, May 23 with United.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Grand Cayman to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Grand Cayman and Chicago start at $1,125 from Fri, Jul 17 to Sun, Jul 26 with American.
The cheapest economy class round-trip flights between Grand Cayman and Chicago start at $366 from Thu, Jun 11 to Wed, Jun 17.
To book business class trips from Grand Cayman to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.
You can also adjust the trip type to view one-way fares.
You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Grand Cayman and Chicago starts at $315 from Sat, Apr 25 to Sun, Apr 26 with United.
The cheapest last-minute deal between Grand Cayman and Chicago at price $315 is offered by United from Sat, Apr 25 to Sun, Apr 26.
To find last-minute flight deals from Grand Cayman to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.
You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.
You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.
Search more flights
Popular trips from Grand Cayman
These suggestions are based on the cheapest fares to popular destinations in the next six months.
Prices include required taxes + fees for 1 adult. Optional charges and bag fees may apply.
-
London$1,190Jun 11 — Jun 172 stops 16 hr 39 min American, British Airways
-
Paris$1,046Jun 4 — Jun 101 stop 14 hr 35 min Air Canada
-
New York$299May 16 — May 251 stop 3 hr 58 min United
-
SingaporeApr 23 — Apr 29
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