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Cheap Flights to Chicago

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Flight Information to Chicago

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Which is the cheapest month to book a flight to Chicago (ORD)?

Currently, October offers the most budget-friendly flights to Chicago. Please note that numerous factors can influence flight costs; therefore, comparing airlines, departure airports, and flight times will consistently provide you with more options.
OriginDestinationDeparture DatePrice
Singapore (SIN)Chicago (CHIA)Thursday, 16 October 2025S$606
Singapore (SIN)Chicago (CHIA)Tuesday, 11 November 2025S$664
Singapore (SIN)Chicago (CHIA)Tuesday, 23 December 2025S$648
Singapore (SIN)Chicago (CHIA)Monday, 19 January 2026S$789
Singapore (SIN)Chicago (CHIA)Monday, 9 February 2026S$742
Singapore (SIN)Chicago (CHIA)Saturday, 14 March 2026S$768
Singapore (SIN)Chicago (CHIA)Wednesday, 15 April 2026S$633
Singapore (SIN)Chicago (CHIA)Saturday, 9 May 2026S$730
Singapore (SIN)Chicago (CHIA)Monday, 1 June 2026S$766
Singapore (SIN)Chicago (CHIA)Wednesday, 1 July 2026No data
Singapore (SIN)Chicago (CHIA)Monday, 10 August 2026S$1,001
Singapore (SIN)Chicago (CHIA)Tuesday, 1 September 2026No data

Flight Schedule to Chicago

Here are all the scheduled flights to Chicago, providing a variety of convenient travel options.
Fri, 3 Oct 2025 (Today)
Sat, 4 Oct 2025
Sun, 5 Oct 2025
Airline
Departure Time
Arrival Time
Origin Airport
Destination Airport
American Airlines
American Airlines
14:22
20:40
San Francisco (SFO)
Chicago (ORD)
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American Airlines
American Airlines
15:38
21:29
Las Vegas (LAS)
Chicago (ORD)
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United Airlines
United Airlines
16:17
18:47
Miami (MIA)
Chicago (ORD)
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Delta Airlines
Delta Airlines
19:30
21:15
Boston (BOS)
Chicago (ORD)
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United Airlines
United Airlines
20:30
22:07
New York (LGA)
Chicago (ORD)
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United Airlines
United Airlines
21:30
23:07
New York (LGA)
Chicago (ORD)
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American Airlines
American Airlines
22:45
23:48
Washington (DCA)
Chicago (ORD)
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United Airlines
United Airlines
22:55
05:06 (+1 day)
Los Angeles (LAX)
Chicago (ORD)
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American Airlines
American Airlines
23:25
05:31 (+1 day)
San Francisco (SFO)
Chicago (ORD)
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United Airlines
United Airlines
23:59
06:10 (+1 day)
Los Angeles (LAX)
Chicago (ORD)
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Seat Class Comparison: Find Your Perfect Fit

Compare the Benefits of Economy, Business, & First Class
Economy
Premium Economy
Business
First Class
MonthSeat ClassAverage Price
OctoberFirst ClassS$12,646
NovemberFirst ClassNo data
DecemberFirst ClassNo data
JanuaryFirst ClassNo data
FebruaryFirst ClassNo data
MarchFirst ClassNo data
AprilFirst ClassNo data
MayFirst ClassNo data
JuneFirst ClassNo data
JulyFirst ClassNo data
AugustFirst ClassNo data
SeptemberFirst ClassNo data
OctoberBusinessS$7,239
NovemberBusinessS$6,088
DecemberBusinessS$6,109
JanuaryBusinessNo data
FebruaryBusinessNo data
MarchBusinessS$6,161
AprilBusinessNo data
MayBusinessNo data
JuneBusinessNo data
JulyBusinessS$5,654
AugustBusinessS$4,764
SeptemberBusinessNo data
OctoberPremium EconomyS$4,079
NovemberPremium EconomyS$3,948
DecemberPremium EconomyS$3,594
JanuaryPremium EconomyS$4,222
FebruaryPremium EconomyNo data
MarchPremium EconomyS$3,604
AprilPremium EconomyS$3,845
MayPremium EconomyNo data
JunePremium EconomyS$3,625
JulyPremium EconomyNo data
AugustPremium EconomyS$3,509
SeptemberPremium EconomyNo data
OctoberEconomyS$1,678
NovemberEconomyS$1,633
DecemberEconomyS$1,563
JanuaryEconomyS$1,933
FebruaryEconomyS$1,288
MarchEconomyS$1,418
AprilEconomyS$1,338
MayEconomyS$1,374
JuneEconomyS$1,520
JulyEconomyNo data
AugustEconomyS$1,528
SeptemberEconomyNo data

Direct flight to Chicago

Non-stop airline flights to Chicago
Select your preferred airline for a direct flight to Chicago. Enjoy a smooth and efficient journey to your destination.
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Southwest Airlines
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Finnair
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