Cheap flights from Cockburn Town to Chicago from £267
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore flight deals to Chicago
Not happy with the results? Try some of our useful filters
Search by stops
- Nonstop
- Up to 1 stop
- Up to 2 stops
Search by departure date
Not happy with the results? Try some of our useful filters
How much do flights to Chicago cost?
Cheapest one-way trip | £267 |
|---|---|
Cheapest round-trip | £459 |
Average round-trip | £599 |
Includes rare itinerary | |
Most popular airline | interCaribbean Airways |
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
Check-in for a flight from Cockburn Town to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| interCaribbean Airways | IWY | JY | No |
| JetBlue Airways | JBU | B6 | No |
| Frontier Airlines | FFT | F9 | No |
| Spirit Airlines | NKS | NK | No |
| WestJet | WJA | WS | 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
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.
Explore alternative trips
Flights from Cockburn Town
Flights to Chicago
Popular routes
Airports near Cockburn Town
Airports near Chicago
Download our app