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S$1,315 Cheap Flights from Chicago to Milan

View S$1,315 flight on Sun, 13 Sept, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Milan

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Cheap Flights from Chicago to Milan (MDW-MIL)

Prices were available within the past 7 days and start at S$1,315 for one-way flights and S$1,329 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air France
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,329 Return, found 6 days ago
S$1,329
Return
found 6 days ago
Select Air France flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,329 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,330 Return, found 6 days ago
S$1,330
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,330 found 6 days ago
Air France
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,342 Return, found 6 days ago
S$1,342
Return
found 6 days ago
Select Air France flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,342 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,344 Return, found 6 days ago
S$1,344
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,344 found 6 days ago
Air France
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,365 Return, found 6 days ago
S$1,365
Return
found 6 days ago
Select Air France flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,365 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,367 Return, found 6 days ago
S$1,367
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,367 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,371 Return, found 6 days ago
S$1,371
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,371 found 6 days ago
Air France
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,378 Return, found 6 days ago
S$1,378
Return
found 6 days ago
Select Air France flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,378 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,380 Return, found 6 days ago
S$1,380
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,380 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,385 Return, found 6 days ago
S$1,385
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,385 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,385 Return, found 6 days ago
S$1,385
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,385 found 6 days ago
Air France
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,395 Return, found 6 days ago
S$1,395
Return
found 6 days ago
Select Air France flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,395 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,397 Return, found 6 days ago
S$1,397
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,397 found 6 days ago
KLM
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,401 Return, found 6 days ago
S$1,401
Return
found 6 days ago
Select KLM flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,401 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,407 Return, found 6 days ago
S$1,407
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,407 found 6 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
MXP
Milan
S$1,408 Return, found 6 days ago
S$1,408
Return
found 6 days ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Milan, returning Wed, 16 Sept, priced at S$1,408 found 6 days ago

Travel information

Origin airport
Midway Intl.
Destination airport
Malpensa Intl.
Return price
S$1,328
Distance
7219 km

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Perfect flights from Chicago to Milan

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*Note: Prices may vary based on availability and are subject to change.
Perfect flights from Chicago to Milan

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