Cheap Flights from Chicago to Milan
Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Milan
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Chicago to Milan
Explore current cheapest deals departing from Chicago to Milan
Round trip
Sort by: Cheapest
October 21 - October 29
ORD - Milan
$777
$566
Round trip
October 17 - October 31
ORD - Milan
$771
$574
Round trip
November 6 - November 13
ORD - Milan
$605
$581
Round trip
December 6 - December 12
ORD - Milan
$960
$582
Round trip
November 3 - November 17
ORD - Milan
$613
$583
Round trip
August 14 - August 21
ORD - Milan
$834
$600
Round trip
August 19 - August 26
ORD - Milan
$840
$604
Round trip
August 16 - August 30
ORD - Milan
$813
$604
Round trip
August 14 - August 20
ORD - Milan
$803
$605
Round trip
August 14 - August 16
ORD - Milan
$835
$605
Round trip
Unlock all 500+ flight deals to Milan and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Milan
How much is a round trip from Chicago to Milan
Regular price: $643 - $1,172
Prices for flights from Chicago to Milan are currently below the regular range.
The regular price range for this route is between $643 and $1172. The current lowest deal is $566 with Scandinavian Airlines, for travel from Oct 21 to Oct 29.
now $566
Low $643
High $1,172
The cheapest time to fly from Chicago to Milan
The cheapest month to fly from Chicago to Milan is January, with a median price of $585. The most expensive month is May, with a median price of $1295. Prices are generally lower from January to December.
January
Flights from $585
May
Flights from $1,295
Direct flights from Chicago to Milan
United Airlines
Last-minute flights going from Chicago to Milan
Fri, Jul 3
ORD - Milan
Chicago (ORD) - Milan (MXP)
JetBlue Airways
$1,062
$779
One-way
Fri, Jul 3
RFD - Milan
Chicago (RFD) - Milan (BGY)
Allegiant Air
$1,139
$827
One-way
Fri, Jul 3
RFD - Milan
Chicago (RFD) - Milan (BGY)
Allegiant Air
$1,151
$847
One-way
Fri, Jul 3
RFD - Milan
Chicago (RFD) - Milan (BGY)
Allegiant Air
$1,168
$848
One-way
Mon, Jul 6
ORD - Milan
Chicago (ORD) - Milan (BGY)
Icelandair
$1,080
$857
One-way
Tue, Jul 7
MDW - Milan
Chicago (MDW) - Milan (BGY)
Porter Airlines
$1,208
$856
One-way
Biggest price drops on these dates for flights from Chicago to Milan
Jul 15 - Jul 20
$1,155 → $721
38%
Jul 15 - Jul 22
$1,187 → $798
33%
Dec 6 - Dec 12
$960 → $582
39%
Dec 4 - Dec 6
$970 → $610
37%
Popular Airports to fly from Chicago to Milan
Chicago - Milan route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Chicago to Milan are above the typical level at $1017.
📅 Best time to fly
January is historically the cheapest month to fly
Historically, January is the cheapest month to fly, with a median price of $585.
⏱️ Flight duration
Connecting flights take 32h 9m on average
Flights from Chicago to Milan typically take 32h 9m, with two stopovers on connecting routes.
✈️ Airlines & availability
Connecting flights are dominant on this route
Only 4.6% of recent deals are direct, making connecting flights dominant on this route.
🏆 Airline highlight
United Airlines offers direct flights
United Airlines has offered direct flights from Chicago to Milan in recent deals.
🎯 Booking tip
Deals appear frequently, about once per day
Deals from Chicago to Milan appear frequently, with about one deal per day.
Chicago main airports to depart from
O Hare International (ORD)
Depart from O'Hare International for flights from Chicago to Milan, often providing competitive prices.
📍 ~25 km from Chicago city center (reachable by car or train)
💸 Flights from ~$566
Chicago Midway International (MDW)
Consider Chicago Midway International for your departure from Chicago to Milan.
📍 ~15 km from Chicago city center (reachable by car or train)
💸 Flights from ~$738
Chicago Rockford International (RFD)
Chicago Rockford International offers another option for flights from Chicago to Milan.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$975
Milan main airports to arrive at
Milan–Malpensa (MXP)
Milan–Malpensa is a good arrival airport for flights from Chicago to Milan, with flights from $566.
📍 ~40 km from Milan (reachable by car)
💸 Flights from ~$566
Linate (LIN)
Linate is a convenient arrival airport for flights from Chicago to Milan.
📍 ~10 km from Milan (reachable by car)
💸 Flights from ~$636
Milan Bergamo International Airport (BGY)
Milan Bergamo International Airport is an option for flights from Chicago to Milan.
📍 ~45 km from Milan (reachable by car)
💸 Flights from ~$611
Airports nearby Milan used as alternative
Turin (TRN)
Turin Airport is a reliable alternative for European and some long-haul routes, with a wide range of cabin classes.
📍 ~120 km from Milan (reachable by car or train)
💸 Flights from ~$710
Bologna Guglielmo Marconi (BLQ)
Bologna Guglielmo Marconi Airport is a major international hub, highly accessible via high-speed rail in about one hour.
📍 ~200 km from Milan (reachable by car or train)
💸 Flights from ~$627
Verona Villafranca (VRN)
Verona Villafranca Airport offers strong regional connectivity and reliable service, with reasonable driving distance.
📍 ~140 km from Milan (reachable by car or train)
💸 Flights from ~$850
Genoa Cristoforo Colombo (GOA)
Genoa Cristoforo Colombo Airport is useful for specific Mediterranean and European connections, located relatively close to Milan.
📍 ~120 km from Milan (reachable by car or train)
💸 Flights from ~$714
Zürich Airport (ZRH)
Zürich Airport is a major global hub offering extensive long-haul flights, with direct rail connections to Milan.
📍 ~220 km from Milan (reachable by car or train)
💸 Flights from ~$598
Business & First Class Flight Deals to Milan
Discover luxury on the budget with premium cabin class on flights from Chicago to Milan.
Elite
Best Elite deals to Milan
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Sep 14
Milan, Italy
95% AI deal score
$2,722
$1,516
Save $1,206
From ORD
Elite
Nov 01
Milan, Italy
94% AI deal score
$2,343
$1,340
Save $1,003
From ORD
Elite
Aug 30
Milan, Italy
94% AI deal score
$2,478
$1,472
Save $1,006
From ORD
Elite
Aug 30
Milan, Italy
94% AI deal score
$2,478
$1,472
Save $1,006
From ORD
Elite
Sep 14
Milan, Italy
94% AI deal score
$2,703
$1,523
Save $1,180
From ORD
Elite
Sep 27
Milan, Italy
94% AI deal score
$2,708
$1,546
Save $1,162
From ORD
Elite
Sep 28
Milan, Italy
94% AI deal score
$2,708
$1,546
Save $1,162
From ORD
Elite
Sep 14
Milan, Italy
94% AI deal score
$2,722
$1,569
Save $1,153
From ORD
Elite
Sep 18
Milan, Italy
94% AI deal score
$2,689
$1,633
Save $1,056
From ORD
Elite
Sep 18
Milan, Italy
94% AI deal score
$2,698
$1,633
Save $1,065
From ORD
Elite
Sep 24
Milan, Italy
94% AI deal score
$2,666
$1,637
Save $1,029
From ORD
Elite
Aug 16
Milan, Italy
93% AI deal score
$2,462
$1,486
Save $976
From ORD
Elite
Aug 23
Milan, Italy
93% AI deal score
$2,464
$1,511
Save $953
From ORD
Elite
Aug 22
Milan, Italy
93% AI deal score
$2,486
$1,520
Save $966
From ORD
Elite
Nov 01
Milan, Italy
93% AI deal score
$2,391
$1,533
Save $858
From ORD
Elite
Aug 05
Milan, Italy
93% AI deal score
$2,490
$1,536
Save $954
From ORD
Elite
Aug 14
Milan, Italy
93% AI deal score
$2,484
$1,565
Save $919
From ORD
Elite
Aug 26
Milan, Italy
93% AI deal score
$2,482
$1,570
Save $912
From ORD
Elite
Aug 25
Milan, Italy
93% AI deal score
$2,483
$1,595
Save $888
From ORD
Elite
Sep 02
Milan, Italy
93% AI deal score
$2,664
$1,690
Save $974
From ORD
Elite
Sep 11
Milan, Italy
93% AI deal score
$2,698
$1,741
Save $957
From ORD
Elite
Sep 15
Milan, Italy
93% AI deal score
$2,710
$1,749
Save $961
From ORD
Elite
Jul 27
Milan, Italy
92% AI deal score
$4,770
$2,852
Save $1,918
From ORD
Elite
Aug 12
Milan, Italy
92% AI deal score
$2,462
$1,597
Save $865
From ORD
Elite
Oct 10
Milan, Italy
92% AI deal score
$2,400
$1,645
Save $755
From ORD
Elite
Sep 06
Milan, Italy
92% AI deal score
$2,658
$1,757
Save $901
From ORD
Elite
Sep 14
Milan, Italy
92% AI deal score
$2,680
$1,768
Save $912
From ORD
Elite
Sep 28
Milan, Italy
92% AI deal score
$2,690
$1,802
Save $888
From ORD
Elite
Sep 05
Milan, Italy
92% AI deal score
$2,697
$1,805
Save $892
From ORD
Elite
Sep 12
Milan, Italy
92% AI deal score
$2,711
$1,814
Save $897
From ORD
Elite
Jul 27
Milan, Italy
92% AI deal score
$2,780
$1,903
Save $877
From ORD
Elite
Sep 11
Milan, Italy
92% AI deal score
$2,707
$1,906
Save $801
From ORD
Elite
Jul 16
Milan, Italy
92% AI deal score
$2,774
$1,916
Save $858
From ORD
Elite
Jul 09
Milan, Italy
92% AI deal score
$2,808
$1,937
Save $871
From ORD
Elite
Dec 07
Milan, Italy
91% AI deal score
$5,327
$3,477
Save $1,850
From ORD
Elite
Dec 02
Milan, Italy
91% AI deal score
$5,348
$3,519
Save $1,829
From ORD
Elite
Oct 14
Milan, Italy
91% AI deal score
$2,384
$1,751
Save $633
From ORD
Elite
Nov 27
Milan, Italy
91% AI deal score
$2,369
$1,781
Save $588
From ORD
Elite
Aug 12
Milan, Italy
91% AI deal score
$2,454
$1,822
Save $632
From ORD
Elite
Oct 11
Milan, Italy
90% AI deal score
$2,380
$1,826
Save $554
From ORD
Elite
Oct 01
Milan, Italy
90% AI deal score
$2,379
$1,829
Save $550
From ORD
Elite
Aug 15
Milan, Italy
90% AI deal score
$2,462
$1,839
Save $623
From ORD
Elite
Oct 06
Milan, Italy
90% AI deal score
$2,381
$1,845
Save $536
From ORD
Elite
Aug 08
Milan, Italy
90% AI deal score
$2,504
$1,971
Save $533
From ORD
Elite
Aug 10
Milan, Italy
90% AI deal score
$2,486
$1,988
Save $498
From ORD
Elite
Jul 27
Milan, Italy
89% AI deal score
$3,371
$2,707
Save $664
From ORD
Elite
Aug 24
Milan, Italy
89% AI deal score
$3,793
$2,848
Save $945
From ORD
Elite
Aug 25
Milan, Italy
89% AI deal score
$3,801
$2,848
Save $953
From ORD
Elite
Aug 24
Milan, Italy
89% AI deal score
$3,778
$2,850
Save $928
From ORD
Elite
Aug 25
Milan, Italy
89% AI deal score
$3,798
$2,850
Save $948
From ORD
Elite
Aug 24
Milan, Italy
89% AI deal score
$3,749
$2,850
Save $899
From ORD
Elite
Aug 25
Milan, Italy
89% AI deal score
$3,763
$2,850
Save $913
From ORD
Elite
Aug 24
Milan, Italy
89% AI deal score
$3,792
$2,851
Save $941
From ORD
Elite
Aug 25
Milan, Italy
89% AI deal score
$3,794
$2,851
Save $943
From ORD
Elite
Aug 26
Milan, Italy
89% AI deal score
$3,794
$2,921
Save $873
From ORD
Elite
Aug 26
Milan, Italy
89% AI deal score
$3,801
$2,923
Save $878
From ORD
Elite
Aug 26
Milan, Italy
89% AI deal score
$3,776
$2,923
Save $853
From ORD
Elite
Aug 26
Milan, Italy
89% AI deal score
$3,822
$2,924
Save $898
From ORD
Elite
Aug 24
Milan, Italy
89% AI deal score
$4,003
$2,961
Save $1,042
From ORD
Elite
Aug 13
Milan, Italy
89% AI deal score
$2,485
$1,971
Save $514
From ORD
Elite
Aug 17
Milan, Italy
89% AI deal score
$2,462
$1,976
Save $486
From ORD
Elite
Aug 06
Milan, Italy
89% AI deal score
$2,455
$1,981
Save $474
From ORD
Elite
Aug 13
Milan, Italy
89% AI deal score
$2,503
$2,021
Save $482
From ORD
Elite
Nov 04
Milan, Italy
85% AI deal score
$4,633
$3,477
Save $1,156
From ORD
Elite
Nov 24
Milan, Italy
85% AI deal score
$4,591
$3,477
Save $1,114
From ORD
Elite
Nov 12
Milan, Italy
85% AI deal score
$2,369
$1,973
Save $396
From ORD
Elite
Aug 24
Milan, Italy
84% AI deal score
$3,548
$2,998
Save $550
From ORD
Elite
Aug 26
Milan, Italy
83% AI deal score
$3,322
$2,836
Save $486
From ORD
Elite
Aug 26
Milan, Italy
83% AI deal score
$3,327
$2,838
Save $489
From ORD
Elite
Aug 26
Milan, Italy
83% AI deal score
$3,305
$2,838
Save $467
From ORD
Elite
Aug 26
Milan, Italy
83% AI deal score
$3,349
$2,839
Save $510
From ORD
Elite
Aug 24
Milan, Italy
83% AI deal score
$3,318
$2,844
Save $474
From ORD
Elite
Aug 24
Milan, Italy
83% AI deal score
$3,305
$2,846
Save $459
From ORD
Elite
Nov 25
Milan, Italy
83% AI deal score
$4,547
$3,491
Save $1,056
From ORD
Elite
Jul 19
Milan, Italy
83% AI deal score
$17,851
$16,130
Save $1,721
From ORD
Elite
Nov 17
Milan, Italy
83% AI deal score
$2,289
$1,921
Save $368
From ORD
Elite
Aug 24
Milan, Italy
82% AI deal score
$3,267
$2,846
Save $421
From ORD
Elite
Sep 04
Milan, Italy
82% AI deal score
$18,417
$16,130
Save $2,287
From ORD
Elite
Sep 11
Milan, Italy
82% AI deal score
$18,221
$16,130
Save $2,091
From ORD
Elite
Aug 04
Milan, Italy
82% AI deal score
$18,222
$16,130
Save $2,092
From ORD
Elite
Sep 03
Milan, Italy
82% AI deal score
$18,471
$16,130
Save $2,341
From ORD
Elite
Sep 10
Milan, Italy
82% AI deal score
$18,221
$16,130
Save $2,091
From ORD
Elite
Aug 01
Milan, Italy
82% AI deal score
$19,371
$16,738
Save $2,633
From ORD
Elite
Aug 24
Milan, Italy
81% AI deal score
$3,319
$2,953
Save $366
From ORD
Elite
Jul 27
Milan, Italy
81% AI deal score
$3,328
$3,001
Save $327
From ORD
Elite
Nov 26
Milan, Italy
81% AI deal score
$4,113
$3,445
Save $668
From ORD
Elite
Nov 29
Milan, Italy
81% AI deal score
$4,095
$3,522
Save $573
From ORD
Elite
Aug 08
Milan, Italy
81% AI deal score
$17,824
$16,114
Save $1,710
From ORD
Elite
Aug 06
Milan, Italy
81% AI deal score
$17,781
$16,130
Save $1,651
From ORD
Elite
Jul 16
Milan, Italy
81% AI deal score
$17,109
$16,130
Save $979
From ORD
Elite
Sep 12
Milan, Italy
81% AI deal score
$17,972
$16,130
Save $1,842
From ORD
Elite
Aug 28
Milan, Italy
81% AI deal score
$17,859
$16,329
Save $1,530
From ORD
Elite
Sep 14
Milan, Italy
81% AI deal score
$18,675
$16,775
Save $1,900
From ORD
Elite
Oct 09
Milan, Italy
80% AI deal score
$17,311
$16,293
Save $1,018
From ORD
Elite
Sep 25
Milan, Italy
80% AI deal score
$17,295
$16,329
Save $966
From ORD
Elite
Oct 07
Milan, Italy
79% AI deal score
$16,784
$16,329
Save $455
From ORD
Elite
Jul 16
Milan, Italy
78% AI deal score
$16,145
$16,130
Save $15
From ORD
Elite
Jul 15
Milan, Italy
78% AI deal score
$16,156
$16,130
Save $26
From ORD
Elite
Nov 10
Milan, Italy
78% AI deal score
$16,329
From ORD
Elite
Oct 16
Milan, Italy
78% AI deal score
$16,775