Cheap flights from Kailua to Chicago from £269
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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 carrier
Search by price
Search by departure date
How much do flights to Chicago cost?
Cheapest one-way trip | £269 |
|---|---|
Cheapest round-trip | £493 |
Average round-trip | £662 |
Most popular airline | Alaska Airlines |
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.
How to get from O'Hare International Airport (ORD) to Chicago?
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 |
How to get from Chicago Midway International Airport (MDW) to Chicago?
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 Kailua to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Alaska Airlines | ASA | AS | No |
| Porter Airlines | POE | PD | No |
| United Airlines | UAL | UA | No |
| Air Canada | ACA | AC | Yes |
| 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 | 5°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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