Cheap Flights from Milano to Chicago
Looking for cheap flights from Milano to Chicago? 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 Milano to Chicago vary by season and date, but economy flights can start around 25,500–40,000 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 Milano to Chicago for specific travel dates.
2026-04-27
MXP - ORD
Economy | Non stop | 9+ left
From 30,000 Pts + $73.7
2026-04-28
MXP - ORD
Economy | Non stop | 9+ left
From 30,000 Pts + $73.7
2026-04-29
MXP - ORD
Economy | Non stop | 9+ left
From 30,000 Pts + $73.7
2026-04-30
MXP - ORD
Economy | Non stop | 9+ left
From 30,000 Pts + $73
2026-04-30
MXP - ORD
Economy | Non stop | 9+ left
From 40,000 Pts + $49.3
2026-04-30
LIN - ORD
Economy | 1 Stop | 5 left
From 25,500 Pts + $220.9
Premium cabin flights from Milano to Chicago
Premium cabin
2026-04-30
MXP - ORD
Business | 1 Stop | 9+ left
From 88,000 Pts + $65.1
Premium cabin
2026-04-30
MXP - ORD
Business | 1 Stop | 9+ left
From 70,000 Pts + $136.1
Premium cabin
2026-05-10
MXP - ORD
Business | 1 Stop | 1 left
From 85,000 Pts + $129.9
Premium cabin
2026-05-10
MXP - ORD
Business | 1 Stop
From 57,500 Pts + $117.4
Premium cabin
2026-05-10
MXP - ORD
Business | 1 Stop
From 93,600 Pts + $304.6
Premium cabin
2026-05-13
MXP - ORD
Business | 1 Stop
From 57,500 Pts + $919
Selected hotels for your next stay
Chicago (United States)
Thompson Chicago
From 17,000 Pts or $220
Vernon Hills (United States)
Hotel Indigo Chicago-Vernon Hills
From 17,000 Pts or $115
Chicago (United States)
Chicago Athletic Association
From 17,000 Pts or $355
Frequently Asked Questions
The cheapest route from Milano to Chicago 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 Milano to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Milano to Chicago.
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