Cheap Flights from Chicago to Milano
Looking for cheap flights from Chicago to Milano? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to Milano vary by season and date, but economy flights can start around 27,500–40,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to Milano for specific travel dates.
2026-04-22
ORD - MXP
Economy | 1 Stop | 4 left
From 27,500 Pts + $18.1
2026-04-22
ORD - MXP
Economy | 1 Stop
From 30,000 Pts + $5.6
2026-04-22
ORD - MXP
Economy | 2 Stops | 1 left
From 39,200 Pts + $103.9
2026-04-23
ORD - MXP
Economy | 1 Stop
From 29,000 Pts + $349
2026-04-23
ORD - MXP
Economy | 1 Stop | 9+ left
From 27,500 Pts + $18.1
2026-04-23
ORD - MXP
Economy | 1 Stop | 9+ left
From 40,000 Pts + $150.8
Premium cabin flights from Chicago to Milano
Premium cabin
2026-04-24
ORD - MXP
Business | 2 Stops | 1 left
From 85,000 Pts + $188.3
Premium cabin
2026-04-25
ORD - MXP
Business | 2 Stops | 4 left
From 85,000 Pts + $1438.1
Premium cabin
2026-04-25
ORD - MXP
Business | 2 Stops
From 57,500 Pts + $759.6
Premium cabin
2026-04-25
ORD - MXP
Business | 2 Stops
From 109,300 Pts + $1425.6
Premium cabin
2026-04-26
ORD - MXP
Business | 1 Stop | 2 left
From 88,000 Pts + $30.4
Premium cabin
2026-04-26
ORD - MXP
Business | 1 Stop | 2 left
From 85,210 Pts + $74.8
Selected hotels for your next stay
Monza (Italy)
Hotel de la Ville - Monza(SLH)
From 50,000 Pts or $209
Breuil Cervinia (Italy)
VRetreats Cervino, an SLH Hotel
From 80,000 Pts or $230
Milan (Italy)
Galleria Vik Milano, an SLH Hotel
From 105,000 Pts or $465
Frequently Asked Questions
The cheapest route from Chicago to Milano depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to Milano.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Milano.
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