Cheap Flights from Singapore to Chicago
Browse current best options from Singapore. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Singapore
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
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 Singapore to Chicago
Explore current cheapest deals departing from Singapore to Chicago
Round trip
Sort by: Cheapest
October 17 - October 22
SIN - Chicago
$1,074
$813
Round trip
September 10 - September 25
SIN - Chicago
$879
$814
Round trip
October 15 - October 25
SIN - Chicago
$1,044
$814
Round trip
November 13 - November 24
SIN - Chicago
$1,059
$815
Round trip
November 10 - November 17
SIN - Chicago
$1,062
$844
Round trip
September 9 - September 16
SIN - Chicago
$913
$845
Round trip
September 20 - September 30
SIN - Chicago
$889
$845
Round trip
September 15 - September 30
SIN - Chicago
$882
$846
Round trip
September 1 - September 9
SIN - Chicago
$878
$846
Round trip
September 20 - September 28
SIN - Chicago
$895
$847
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Singapore to Chicago
How much is a round trip from Singapore to Chicago
Regular price: $937 - $1,649
Prices are currently below the regular range for flights from Singapore to Chicago.
The regular price range for this route is $937 to $1649. The lowest deal found is $813 with Air Canada, for travel from Oct 17 to Oct 22.
now $813
Low $937
High $1,649
The cheapest time to fly from Singapore to Chicago
The cheapest month to fly from Singapore to Chicago is September, with a median price of $580. The most expensive month is August, with a median price of $1805. Prices are generally lower from January to November.
September
Flights from $580
August
Flights from $1,805
Direct flights from Singapore to Chicago
Korean Air
Air Canada
All Nippon Airways
Cathay Pacific
Last-minute flights going from Singapore to Chicago
Sat, Jun 20
SIN - Chicago
Singapore (SIN) - Chicago (ORD)
EVA Air
$1,021
$1,194
One-way
Thu, Jun 25
SIN - Chicago
Singapore (SIN) - Chicago (ORD)
Japan Airlines
$978
$1,176
One-way
Fri, Jul 3
SIN - Chicago
Singapore (SIN) - Chicago (ORD)
EVA Air
$945
$1,249
One-way
Mon, Jul 6
SIN - Chicago
Singapore (SIN) - Chicago (ORD)
Air Canada
$928
$947
One-way
Tue, Jul 7
SIN - Chicago
Singapore (SIN) - Chicago (ORD)
Air Canada
$962
$873
One-way
Wed, Jul 8
SIN - Chicago
Singapore (SIN) - Chicago (ORD)
All Nippon Airways
$933
$1,165
One-way
Biggest price drops on these dates for flights from Singapore to Chicago
Oct 17 - Oct 22
$1,074 → $813
24%
Oct 9 - Oct 11
$1,411 → $1,160
18%
Nov 13 - Nov 24
$1,059 → $815
23%
Nov 1 - Nov 5
$1,083 → $850
22%
Popular Airports to fly from Singapore to Chicago
Singapore - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Singapore to Chicago are $813, which is below the typical level for this route.
📅 Best time to fly
September is historically cheapest at $580
Historically, September is the cheapest month to fly from Singapore to Chicago, with a median price of $580.
⏱️ Flight duration
Flights are typically 28h 42m
The median flight duration from Singapore to Chicago is 28 hours and 42 minutes, including layovers.
✈️ Airlines & availability
Connecting flights are dominant
Connecting flights are dominant on this route, with a median of 1 stopover for deals found.
🏆 Airline highlight
Air Canada offers a recent deal for $813
Air Canada recently offered a flight from Singapore to Chicago for $813.
🎯 Booking tip
Deals appear frequently (0.67 per day)
Deals for flights from Singapore to Chicago appear frequently, with about 0.67 deals per day.
Singapore main airports to depart from
Singapore Changi (SIN)
Singapore Changi is a great option for flights from Singapore to Chicago, offering competitive prices.
📍 ~18 km from city center (reachable by car or train)
💸 Flights from ~$813
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago from Singapore, offering many travel options.
📍 ~25 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$813
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient option for travelers arriving in Chicago from Singapore.
📍 ~15 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$1160
Chicago Rockford International (RFD)
Chicago Rockford International Airport provides an alternative arrival point for flights to Chicago from Singapore.
📍 ~120 km from Chicago city center (reachable by car).
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$1229
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, connected by commuter rail.
📍 ~120 km from Chicago (reachable by car or train)
💸 Flights from ~$1303
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, a good alternative for travelers on the eastern side of Chicago.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$1140
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport, less congested than major Chicago hubs.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$1378
Fort Wayne International (FWA)
Fort Wayne International offers stable regional service, an alternative for southeastern Chicago suburbs.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$1258
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Singapore to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From SIN
Elite
Oct 21
Chicago, United States
91% AI deal score
$5,521
$3,829
Save $1,692
From SIN
Elite
Oct 21
Chicago, United States
91% AI deal score
$5,487
$3,832
Save $1,655
From SIN
Elite
Oct 28
Chicago, United States
91% AI deal score
$5,572
$3,881
Save $1,691
From SIN
Elite
Oct 28
Chicago, United States
91% AI deal score
$5,489
$3,884
Save $1,605
From SIN
Elite
Oct 21
Chicago, United States
91% AI deal score
$5,487
$3,887
Save $1,600
From SIN
Elite
Oct 28
Chicago, United States
91% AI deal score
$5,533
$3,939
Save $1,594
From SIN
Elite
Sep 10
Chicago, United States
91% AI deal score
$2,377
$1,853
Save $524
From SIN
Elite
Sep 15
Chicago, United States
91% AI deal score
$2,361
$1,853
Save $508
From SIN
Elite
Jun 23
Chicago, United States
91% AI deal score
$2,380
$1,881
Save $499
From SIN
Elite
Nov 10
Chicago, United States
90% AI deal score
$4,896
$3,815
Save $1,081
From SIN
Elite
Nov 10
Chicago, United States
90% AI deal score
$4,978
$3,815
Save $1,163
From SIN
Elite
Nov 10
Chicago, United States
90% AI deal score
$4,888
$3,815
Save $1,073
From SIN
Elite
Nov 10
Chicago, United States
90% AI deal score
$4,959
$3,870
Save $1,089
From SIN
Elite
Nov 17
Chicago, United States
90% AI deal score
$4,906
$3,879
Save $1,027
From SIN
Elite
Nov 17
Chicago, United States
90% AI deal score
$4,906
$3,879
Save $1,027
From SIN
Elite
Jul 22
Chicago, United States
90% AI deal score
$6,221
$4,601
Save $1,620
From SIN
Elite
Jul 24
Chicago, United States
90% AI deal score
$6,116
$4,605
Save $1,511
From SIN
Elite
Sep 10
Chicago, United States
90% AI deal score
$2,305
$1,853
Save $452
From SIN
Elite
Sep 13
Chicago, United States
90% AI deal score
$2,310
$1,853
Save $457
From SIN
Elite
Sep 15
Chicago, United States
90% AI deal score
$2,341
$1,853
Save $488
From SIN
Elite
Sep 03
Chicago, United States
90% AI deal score
$2,291
$1,853
Save $438
From SIN
Elite
Sep 13
Chicago, United States
90% AI deal score
$2,342
$1,853
Save $489
From SIN
Elite
Sep 03
Chicago, United States
90% AI deal score
$2,247
$1,853
Save $394
From SIN
Elite
Sep 10
Chicago, United States
90% AI deal score
$2,338
$1,853
Save $485
From SIN
Elite
Sep 11
Chicago, United States
90% AI deal score
$2,338
$1,860
Save $478
From SIN
Elite
Sep 11
Chicago, United States
90% AI deal score
$2,261
$1,860
Save $401
From SIN
Elite
Sep 13
Chicago, United States
90% AI deal score
$2,266
$1,860
Save $406
From SIN
Elite
Sep 03
Chicago, United States
90% AI deal score
$2,323
$1,871
Save $452
From SIN
Elite
Sep 14
Chicago, United States
90% AI deal score
$2,362
$1,871
Save $491
From SIN
Elite
Sep 01
Chicago, United States
90% AI deal score
$2,347
$1,879
Save $468
From SIN
Elite
Sep 01
Chicago, United States
90% AI deal score
$2,365
$1,879
Save $486
From SIN
Elite
Jun 29
Chicago, United States
90% AI deal score
$2,333
$1,880
Save $453
From SIN
Elite
Jun 28
Chicago, United States
90% AI deal score
$2,335
$1,880
Save $455
From SIN
Elite
Sep 14
Chicago, United States
90% AI deal score
$2,342
$1,880
Save $462
From SIN
Elite
Jun 22
Chicago, United States
90% AI deal score
$2,342
$1,881
Save $461
From SIN
Elite
Jun 25
Chicago, United States
90% AI deal score
$2,279
$1,881
Save $398
From SIN
Elite
Sep 11
Chicago, United States
90% AI deal score
$2,359
$1,881
Save $478
From SIN
Elite
Jun 19
Chicago, United States
90% AI deal score
$2,280
$1,881
Save $399
From SIN
Elite
Jun 20
Chicago, United States
90% AI deal score
$2,290
$1,888
Save $402
From SIN
Elite
Jul 24
Chicago, United States
89% AI deal score
$5,926
$4,601
Save $1,325
From SIN
Elite
Sep 04
Chicago, United States
89% AI deal score
$5,710
$4,605
Save $1,105
From SIN
Elite
Dec 02
Chicago, United States
89% AI deal score
$5,982
$4,624
Save $1,358
From SIN
Elite
Jul 08
Chicago, United States
89% AI deal score
$20,867
$16,303
Save $4,564
From SIN
Elite
Jul 26
Chicago, United States
89% AI deal score
$20,927
$16,335
Save $4,592
From SIN
Elite
Jul 27
Chicago, United States
89% AI deal score
$21,030
$16,337
Save $4,693
From SIN
Elite
Jul 29
Chicago, United States
88% AI deal score
$5,720
$4,605
Save $1,115
From SIN
Elite
Sep 04
Chicago, United States
88% AI deal score
$5,647
$4,605
Save $1,042
From SIN
Elite
Jul 22
Chicago, United States
88% AI deal score
$5,720
$4,614
Save $1,106
From SIN
Elite
Jul 28
Chicago, United States
88% AI deal score
$5,720
$4,624
Save $1,096
From SIN
Elite
Jul 22
Chicago, United States
88% AI deal score
$5,671
$4,624
Save $1,047
From SIN
Elite
Jul 31
Chicago, United States
88% AI deal score
$5,730
$4,640
Save $1,090
From SIN
Elite
Jul 30
Chicago, United States
88% AI deal score
$5,730
$4,640
Save $1,090
From SIN
Elite
Jul 14
Chicago, United States
88% AI deal score
$20,210
$16,274
Save $3,936
From SIN
Elite
Jul 20
Chicago, United States
88% AI deal score
$20,210
$16,274
Save $3,936
From SIN
Elite
Jul 31
Chicago, United States
87% AI deal score
$5,681
$4,640
Save $1,041
From SIN
Elite
Jul 04
Chicago, United States
84% AI deal score
$18,819
$15,550
Save $3,269
From SIN
Elite
Aug 31
Chicago, United States
84% AI deal score
$2,216
$1,880
Save $336
From SIN
Elite
Sep 10
Chicago, United States
84% AI deal score
$2,185
$1,881
Save $304
From SIN
Elite
Jul 07
Chicago, United States
83% AI deal score
$5,581
$4,624
Save $957
From SIN
Elite
Jul 05
Chicago, United States
83% AI deal score
$18,489
$15,679
Save $2,810
From SIN
Elite
Nov 03
Chicago, United States
83% AI deal score
$20,332
$16,223
Save $4,109
From SIN
Elite
Jul 29
Chicago, United States
83% AI deal score
$18,677
$16,252
Save $2,425
From SIN
Elite
Jul 31
Chicago, United States
83% AI deal score
$18,667
$16,252
Save $2,415
From SIN
Elite
Sep 08
Chicago, United States
83% AI deal score
$19,614
$16,264
Save $3,350
From SIN
Elite
Jul 19
Chicago, United States
83% AI deal score
$19,407
$16,336
Save $3,071
From SIN
Elite
Jul 27
Chicago, United States
83% AI deal score
$2,247
$1,912
Save $335
From SIN
Elite
Sep 01
Chicago, United States
82% AI deal score
$5,361
$4,640
Save $721
From SIN
Elite
Aug 05
Chicago, United States
82% AI deal score
$18,986
$16,248
Save $2,738
From SIN
Elite
Dec 03
Chicago, United States
82% AI deal score
$19,318
$16,274
Save $3,044
From SIN
Elite
Dec 07
Chicago, United States
82% AI deal score
$19,523
$16,274
Save $3,249
From SIN
Elite
Dec 02
Chicago, United States
82% AI deal score
$19,318
$16,274
Save $3,044
From SIN
Elite
Jul 09
Chicago, United States
82% AI deal score
$18,919
$16,274
Save $2,645
From SIN
Elite
Sep 13
Chicago, United States
82% AI deal score
$19,543
$16,274
Save $3,269
From SIN
Elite
Aug 04
Chicago, United States
82% AI deal score
$18,922
$16,289
Save $2,633
From SIN
Elite
Dec 08
Chicago, United States
82% AI deal score
$19,523
$16,303
Save $3,220
From SIN
Elite
Jul 31
Chicago, United States
82% AI deal score
$18,608
$16,303
Save $2,305
From SIN
Elite
Jul 08
Chicago, United States
82% AI deal score
$18,726
$16,303
Save $2,423
From SIN
Elite
Jul 31
Chicago, United States
82% AI deal score
$18,667
$16,332
Save $2,335
From SIN
Elite
Jul 09
Chicago, United States
82% AI deal score
$18,726
$16,336
Save $2,390
From SIN
Elite
Sep 07
Chicago, United States
82% AI deal score
$19,539
$16,337
Save $3,202
From SIN
Elite
Sep 01
Chicago, United States
81% AI deal score
$18,320
$16,186
Save $2,134
From SIN
Elite
Sep 02
Chicago, United States
81% AI deal score
$18,116
$16,223
Save $1,893
From SIN
Elite
Nov 06
Chicago, United States
81% AI deal score
$18,419
$16,244
Save $2,175
From SIN
Elite
Jul 29
Chicago, United States
81% AI deal score
$18,417
$16,252
Save $2,165
From SIN
Elite
Aug 31
Chicago, United States
81% AI deal score
$18,667
$16,252
Save $2,415
From SIN
Elite
Aug 13
Chicago, United States
81% AI deal score
$18,508
$16,270
Save $2,238
From SIN
Elite
Nov 07
Chicago, United States
81% AI deal score
$18,355
$16,274
Save $2,081
From SIN
Elite
Nov 15
Chicago, United States
81% AI deal score
$18,394
$16,274
Save $2,120
From SIN
Elite
Nov 13
Chicago, United States
81% AI deal score
$18,458
$16,274
Save $2,184
From SIN
Elite
Aug 07
Chicago, United States
81% AI deal score
$18,636
$16,275
Save $2,361
From SIN
Elite
Aug 06
Chicago, United States
81% AI deal score
$18,718
$16,284
Save $2,434
From SIN
Elite
Sep 03
Chicago, United States
81% AI deal score
$18,127
$16,285
Save $1,842
From SIN
Elite
Jul 29
Chicago, United States
81% AI deal score
$18,412
$16,293
Save $2,119
From SIN
Elite
Jul 09
Chicago, United States
81% AI deal score
$18,578
$16,298
Save $2,280
From SIN
Elite
Jul 31
Chicago, United States
81% AI deal score
$18,420
$16,299
Save $2,121
From SIN
Elite
Aug 14
Chicago, United States
81% AI deal score
$18,455
$16,302
Save $2,153
From SIN
Elite
Jul 31
Chicago, United States
81% AI deal score
$18,412
$16,303
Save $2,109
From SIN
Elite
Jul 20
Chicago, United States
81% AI deal score
$18,325
$16,303
Save $2,022
From SIN
Elite
Aug 06
Chicago, United States
81% AI deal score
$18,701
$16,320
Save $2,381
From SIN
Elite
Jul 26
Chicago, United States
81% AI deal score
$18,566
$16,335
Save $2,231