Award flights from Grand Cayman (GCM) to Chicago O’Hare (ORD)
In the last 30 days AwardTool saw award space on 2 programs for GCM→ORD. Lowest economy: 19,000 points + $124.71 (Virgin Australia Velocity). Lowest business class: 58,800 miles (GOL Smiles).
Data as of
Award prices last changed . AwardTool checks these routes daily; seats change quickly.
Grand Cayman (GCM) to Chicago O’Hare (ORD) at a glance
- From
- Owen Roberts International, Grand Cayman, Cayman Islands (GCM)
- To
- Chicago O'Hare International, Chicago, Illinois, United States (ORD)
- Programs with award space seen
- 2 of 2 programs tracked on this route
- Nonstop award space seen
- Yes, in economy and business class, via GOL Smiles and Virgin Australia Velocity
- Airlines seen on these awards
- American Airlines (AA), Air Canada (AC), United Airlines (UA)
- Departures with open awards
- Oct 2026 to Sep 2027
- Observation window
- Awards observed in the last 30 days
- Destination guide
- Award flights to Chicago O’Hare (ORD)
Compare programs by cabin
The lowest one-way award each program showed in each cabin, sorted by points.
Economy
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| Virgin Australia VelocityLowest observed | 19,000 pts + $124.71 | Nonstop | United Airlines (UA) | 9+ | 137 | See dates | |
| GOL Smiles | 30,900 pts + taxes not reported | Nonstop | American Airlines (AA), Air Canada (AC) | 1 | 320 | See dates |
Business Class
| Program | Points + taxes | Stops | Airlines seen | Seats | Dates seen | Newest observation | |
|---|---|---|---|---|---|---|---|
| GOL Smiles | 58,800 pts + taxes not reported | 1 stopNonstop from 67,500 pts · Mixed cabin | American Airlines (AA), Air Canada (AC) | 1 | 271 | See dates |
Not seen in business class: Virgin Australia Velocity.
Premium economy: not seen in the last 30 days.
First class: not seen in the last 30 days.
Not seen means AwardTool hasn't observed this cabin on this route in the last 30 days. It doesn't mean the airline has no seats. Dates seen counts departure dates with an open award in that cabin at any price; newest observation is the latest time AwardTool saw one of them. Seats is the count the program reported when we observed it; some programs report at most 9.
Observed award examples
| Departure | Cabin | Program | Points + taxes | Seats | Stops | Observed (UTC) | |
|---|---|---|---|---|---|---|---|
| Economy | Virgin Australia Velocity | 19,000 pts + $124.71 | 9+ | Nonstop | Check this date | ||
| Business | GOL Smiles | 60,500 pts + taxes not reported | 1 | 1 stop | Check this date |
Prices are one-way per traveler: the program's points or miles plus taxes and carrier fees in USD, as AwardTool observed them at the time shown. Award space changes constantly. A seat we saw may be gone, and space we haven't seen may exist. Always confirm with a live search before transferring points; most transfers can't be reversed.
Nonstop award space
- Economy: nonstop from 19,000 points via Virgin Australia Velocity, which showed nonstop space on 67 dates (2 programs had nonstop space).
- Business class: nonstop from 67,500 miles via GOL Smiles, which showed nonstop space on 18 dates.
Best months to fly from Grand Cayman (GCM) to Chicago O’Hare (ORD) on points
| Month | Economy | Business |
|---|---|---|
| 19,000 · Velocity (7 dates) | 64,800 · Smiles (9 dates) | |
| 19,000 · Velocity (24 dates) | 62,300 · Smiles (23 dates) | |
| 19,000 · Velocity (15 dates) | 60,500 · Smiles (26 dates) | |
| 19,000 · Velocity (14 dates) | 60,500 · Smiles (22 dates) | |
| 19,000 · Velocity (20 dates) | 59,300 · Smiles (22 dates) | |
| 19,000 · Velocity (16 dates) | 59,300 · Smiles (28 dates) | |
| 19,000 · Velocity (16 dates) | 58,800 · Smiles (28 dates) | |
| 19,000 · Velocity (13 dates) | 58,800 · Smiles (24 dates) | |
| 19,000 · Velocity (3 dates) | 58,800 · Smiles (28 dates) | |
| 19,000 · Velocity (8 dates) | 58,800 · Smiles (30 dates) | |
| 32,200 · Smiles (31 dates) | 58,800 · Smiles (31 dates) | |
| 19,000 · Velocity (1 date) | — |
Search, calendar and alerts from Grand Cayman (GCM) to Chicago O’Hare (ORD)
Route calendar
Every departure date with open award seats on GCM→ORD for GOL Smiles and the other programs: a limited window on the free plan and 365 days with Pro.
Open the route calendarLive search
Search one date across programs to see current flights, seats and taxes before you transfer points.
Search Grand Cayman (GCM) to Chicago O’Hare (ORD)Questions about award flights from Grand Cayman (GCM) to Chicago O’Hare (ORD)
What's the lowest Grand Cayman (GCM) to Chicago O’Hare (ORD) award price AwardTool has seen?
In economy, 19,000 points + $124.71 with Virgin Australia Velocity. Virgin Australia Velocity showed economy award space on 137 departure dates (newest observation Oct 14, 2026, 12:35 UTC). In business class, 58,800 miles with GOL Smiles. GOL Smiles showed business-class award space on 271 departure dates (newest observation Oct 6, 2026, 14:37 UTC). Search live before transferring points.
Which loyalty programs had award space from Grand Cayman (GCM) to Chicago O’Hare (ORD)?
2 programs in the last 30 days: GOL Smiles (economy 320 dates, business class 271 dates); Virgin Australia Velocity (economy 137 dates). Dates count departure dates with an open award.
Is there nonstop award space from Grand Cayman (GCM) to Chicago O’Hare (ORD)?
Yes. AwardTool observed nonstop award space in economy and business class, bookable via GOL Smiles and Virgin Australia Velocity. The lowest nonstop award in economy was 19,000 points with Virgin Australia Velocity.
Which months had the lowest award prices from Grand Cayman (GCM) to Chicago O’Hare (ORD)?
Counting only month prices from programs with award space on 2 or more dates that month, and leaving out unusually low outliers: in economy, the lowest award was for Nov 2026 departures, 19,000 points with Velocity (24 dates); in business class, the lowest award was for Aug 2027 departures, 58,800 miles with Smiles (31 dates). The month table shows every lowest price, including those. Based on dates we observed, not a forecast.