Cheap flights from Grand Cayman to Chicago from £146
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How much do flights to Chicago cost?
Getting from Chicago's airport to the city center
Fastest options: CTA Blue Line train from O'Hare. Best value: CTA Orange Line from Midway or shared ride services.
From O'Hare International Airport (ORD)
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
40-50 min | $5 (standard fare) | every 5–10 min (traffic dependent) | budget travelers to Loop | |
60-90 min | $2-$5 (combined bus and Metra fare) | every 20–30 min (traffic dependent) | northwest suburbs connection | |
35-70 min | $45-$65 (metered; varies by traffic) | on-demand 24/7 (traffic dependent) | door-to-door with luggage | |
35-70 min | $35-$75 (surge pricing may apply) | on-demand 24/7 (traffic dependent) | app-based convenience | |
35-70 min | $60-$120 (pre-booked; fixed rate) | by reservation (traffic dependent) | groups or business travel |
From Chicago Midway International Airport (MDW)
Transport Option | Typical Time | Typical Cost | Frequency | Best For |
|---|---|---|---|---|
25-30 min | $5 (standard fare) | every 6–12 min (traffic dependent) | quick access to Loop | |
20-45 min | $30-$45 (metered; varies by traffic) | on-demand 24/7 (traffic dependent) | door-to-door convenience | |
20-45 min | $25-$50 (surge pricing may apply) | on-demand 24/7 (traffic dependent) | flexible pickup location |
Notes:
- Prices in USD; table created in 2025 and subject to change.
- CTA Ventra cards or contactless payment accepted on Blue and Orange Lines.
- Taxis are metered; ride-hailing prices vary with demand. Road traffic can significantly affect journey times.
- We recommend checking official transport websites for your travel planning.
Updated: December 2025
Key info about flying to Chicago
Weekly direct flights
Discover the top airlines offering direct flights from Grand Cayman to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.
| Airline | Mon 02.02 | Tue 03.02 | Wed 04.02 | Thu 05.02 | Fri 06.02 | Sat 07.02 | Sun 08.02 |
|---|---|---|---|---|---|---|---|
| 2 | --- | --- | 1 | 1 | --- | 1 | |
| Weekly flights: 5 total | Daily flights: 0.71 average | Most flights: Monday 2 flights |
| Airline | Mon 09.02 | Tue 10.02 | Wed 11.02 | Thu 12.02 | Fri 13.02 | Sat 14.02 | Sun 15.02 |
|---|---|---|---|---|---|---|---|
| 1 | --- | --- | 1 | 1 | 1 | 1 | |
| Weekly flights: 5 total | Daily flights: 0.71 average | Most flights: Monday 1 flights |
| Airline | Mon 16.02 | Tue 17.02 | Wed 18.02 | Thu 19.02 | Fri 20.02 | Sat 21.02 | Sun 22.02 |
|---|---|---|---|---|---|---|---|
| --- | --- | --- | 1 | 1 | 1 | 1 | |
| Weekly flights: 4 total | Daily flights: 0.57 average | Most flights: Thursday 1 flights |
| Airline | Mon 23.02 | Tue 24.02 | Wed 25.02 | Thu 26.02 | Fri 27.02 | Sat 28.02 | Sun 01.03 |
|---|---|---|---|---|---|---|---|
| 1 | --- | --- | 1 | --- | --- | 1 | |
| Weekly flights: 3 total | Daily flights: 0.43 average | Most flights: Monday 1 flights |
Check-in for a flight from Grand Cayman to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Cayman Airways | CAY | KX | No |
| Spirit Airlines | NKS | NK | No |
| Frontier Airlines | FFT | F9 | No |
| JetBlue Airways | JBU | B6 | No |
| United Airlines | UAL | UA | No |
Online check-in is not available for these airlines.
Weather in Chicago
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | -1°C | -6°C |
| February | 0°C | -5°C |
| March | 6°C | 0°C |
| April | 11°C | 4°C |
| May | 17°C | 10°C |
| June | 22°C | 16°C |
| July | 26°C | 20°C |
| August | 25°C | 19°C |
| September | 22°C | 16°C |
| October | 15°C | 10°C |
| November | 8°C | 3°C |
| December | 2°C | -1°C |
14 day forecast
Frequently asked questions
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