Cheap flights from Milan to Chicago from £365
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How much do flights to Chicago cost?
Cheapest one-way trip | £365 |
|---|---|
Cheapest nonstop round-trip | £665 |
Cheapest round-trip | £643 |
Average round-trip | £700 |
Nonstop flights in May | £719 – £1,297 |
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
Weekly direct flights
Discover the top airlines offering direct flights from Milan to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.
| Airline | Mon 25.05 | Tue 26.05 | Wed 27.05 | Thu 28.05 | Fri 29.05 | Sat 30.05 | Sun 31.05 |
|---|---|---|---|---|---|---|---|
| --- | --- | --- | 2 | 2 | 2 | 2 | |
| --- | --- | --- | --- | 1 | 1 | 1 | |
| Weekly flights: 11 total | Daily flights: 1.57 average | Most flights: Thursday 2 flights |
| Airline | Mon 01.06 | Tue 02.06 | Wed 03.06 | Thu 04.06 | Fri 05.06 | Sat 06.06 | Sun 07.06 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| 1 | 1 | 1 | 1 | --- | 1 | --- | |
| Weekly flights: 19 total | Daily flights: 2.71 average | Most flights: Monday 2 flights |
| Airline | Mon 08.06 | Tue 09.06 | Wed 10.06 | Thu 11.06 | Fri 12.06 | Sat 13.06 | Sun 14.06 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| 1 | --- | --- | 1 | 1 | 1 | --- | |
| Weekly flights: 18 total | Daily flights: 2.57 average | Most flights: Monday 2 flights |
| Airline | Mon 15.06 | Tue 16.06 | Wed 17.06 | Thu 18.06 | Fri 19.06 | Sat 20.06 | Sun 21.06 |
|---|---|---|---|---|---|---|---|
| 2 | 2 | 2 | 2 | 2 | 2 | 2 | |
| --- | 1 | 1 | 1 | 1 | --- | --- | |
| Weekly flights: 18 total | Daily flights: 2.57 average | Most flights: Monday 2 flights |
Check-in for a flight from Milan to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking |
|---|---|---|---|
| Ryanair | RYR | FR | No |
| JetBlue Airways | JBU | B6 | No |
| Porter Airlines | POE | PD | No |
| easyJet | EZY | U2 | 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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