Find cheap flights to Chicago

Search hundreds of travel sites at once for deals on flights to Chicago

Depart
Return
Any month
Compare vs KAYAK |

Singapore to Chicago flight information

Flights arrive in Chicago
Flights depart from Singapore
Flight price S$ 1057
Airlines China Eastern, EVA Air, Delta, Qantas Airways

Top tips for finding cheap flights to Chicago

Looking for cheap airfare to Chicago? 25% of our users found return tickets to Chicago for the following prices or less: From Singapore Changi S$ 1271
Book at least 3 weeks before departure in order to get a below-average price.
High season is considered to be January, February and December. The cheapest month to fly to Chicago is January.
Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

FAQs - Booking Chicago flights

What is the cheapest flight to Chicago?

The cheapest airline ticket to Chicago from Singapore in the last 72 hours was S$ 1057 return on the route Singapore to Chicago. The most popular route is Singapore to Chicago and the cheapest ticket found on this route in the last 72 hours was S$ 1427 return.

Which Chicago airport is closest to central Chicago?

Chicago is served by 3 major airports. Midway (14 kilometres) is the closest to the centre of Chicago, O'Hare Intl is 26 kilometres from the centre and Greater Rockford is 126 kilometres away from the centre. View on map.

Book Cheap Chicago Plane Tickets

(Return)
Airports
Origin
Singapore
S$ 1057
only
S$ 1057
Destination
Chicago
S$ 1057
only
S$ 1057
S$ 1427
only
S$ 1427
Wed, 1 May
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
52h 05m
Tue, 7 May
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
63h 50m
S$ 1057
Trip: 7 days
Overall 0.0 Poor
Based on 0 reviews
Sat, 14 Sep
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
24h 45m
Sat, 21 Sep
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
40h 20m
S$ 1059
Trip: 8 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 6,005 reviews
Overall
6.6
Boarding
6.7
Comfort
6.6
Crew
7.0
Entertainment
6.3
Food
6.1
CTU
PVG
Excellent 8.6

Pros: Crews are good. The seat has more room for leg.

LAX
PVG
Mediocre 2.0

Pros: Nothing terrible

DEL
PVG
Good 6.0

Cons: Got to China. And for some reason they were not handing out 24 hour visas to anyone that morning. Have a 19 hour connection and not allowed to leave the airport. Asked the airline to change the flight so the wait would be significantly less. Very rude China Eastern staff who yelled instead of trying

LAX
PVG
Mediocre 2.0

Cons: I wasn't able to flight I didnt know my passport wasnt any good if it's going to expired in less than 3 months. I was off by just a day. I still cant believe I cant get my money back. My boyfriend and I were already planning to go this time and win December to Thailand. Also Vietnam during October s

JFK
PVG
OK 5.3

Pros: My screen on the first leg didn’t work too well. It would turn on and off on its own, but since it was an overnight flight and I was tired, I slept most of the way so didn’t complain. Just had to dim the screen for the times it would turn on automatically while I was trying to sleep. 2nd leg had

Cons: I understand it is a Chinese airline, but I wish there was more English spoken, or the flight attendants not assume everyone who is Asian understands Chinese, especially since the flights are international.

Fri, 28 Jun
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
20h 50m
Thu, 18 Jul
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
22h 30m
S$ 1258
Trip: 21 days
8.6ExcellentShow reviews
Overall 8.6 Excellent
Based on 5,335 reviews
Overall
8.7
Boarding
8.8
Comfort
8.5
Crew
8.9
Entertainment
8.4
Food
8.3
TPE
MNL
Mediocre 3.6

Pros: Leg room of seats is spacious

Cons: Depart on time

LAX
TPE
Excellent 8.3

Pros: Great entertainment, pretty good food.

Cons: Service was okay but nothing special.

SIN
TPE
Excellent 10.0

Pros: The crew was great

SGN
TPE
Excellent 10.0

Pros: Great crew and very attentive

TPE
PNH
OK 5.0

Pros: Departure on time.

Cons: Me and my wife book the same flight. I was really disappointed with our seats from Taiwan to Phnom Penh. We both got separated with our seats. They need to put people traveling together next to each other.

Sat, 23 Mar
SIN
Singapore Changi
MDW
Chicago Midway
28h 24m
Mon, 1 Apr
MDW
Chicago Midway
SIN
Singapore Changi
27h 30m
S$ 1427
Trip: 10 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
MCO
IND
Good 7.6

Pros: The flight timings and the arrival time

BDL
ATL
Excellent 8.0

Pros: I liked the wide variety of movies and snacks available.

Cons: The kid behind me wouldn't stop kicking my seat.

ORD
LGA
Excellent 10.0

Pros: Flight attendant in first class was amazing.

SJD
ATL
Excellent 8.3

Pros: The crew very nice and helpful

JFK
YYZ
Excellent 10.0

Cons: Good

Fri, 2 Aug
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
37h 00m
Sat, 17 Aug
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
48h 05m
S$ 1437
Trip: 16 days
8.0ExcellentShow reviews
Overall 8.0 Excellent
Based on 4,332 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.9
Food
7.6
SYD
SIN
Good 7.6

Pros: crew was very nice

Cons: entertainment system malfunction needed a long time to reboot

LAX
AKL
Good 6.3

Cons: Baby stroller was sent to baggage claim. I had to walk with small baby and a bunch of bags through all steps instead of using the stroller.

NRT
MEL
Good 7.6

Pros: Fast boarding and great entertainment.

Cons: Food was sparse and water hard to come by. The ability of passengers in front to deeply recline their seats made the flight uncomfortable and claustrophobic.

MEL
LAX
Good 6.6

Pros: This flight had significantly less turbulence than my flight to Melbourne

Cons: The headphone jack to watch movies was broken so I wasn’t able to watch anything over the 14 hour flight. This was especially frustrating because I had to pay for my seat selection and I assumed all of your seats would be in working order.

MEL
SYD
Excellent 9.2

Pros: Lovely crew especially Heidi

Cons: Nothing, all was well

Tue, 30 Apr
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
47h 05m
Wed, 8 May
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
23h 30m
S$ 1115
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Sun, 24 Mar
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
26h 40m
Sun, 31 Mar
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
25h 35m
S$ 1229
Trip: 8 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 6,005 reviews
Overall
6.6
Boarding
6.7
Comfort
6.6
Crew
7.0
Entertainment
6.3
Food
6.1
PVG
ORD
Excellent 10.0

Pros: Everything was perfect . Also they didnt have more chicken food since i don’t eat pork so one of the flight attendent gave me her food so i could nt be starving . Thats was amazing from her . I dnt remember her name but just wanna say thank youP

PVG
CGK
Mediocre 2.0

Cons: They did not let me on the plane due to my middle name not being on my passport. This have never happened to me before in all my years of travel. Worse yet, Kayak (JustFly) did not give me any refund or change my flight. It was "their policy." I will never use JustFly or China Eastern again.

JFK
PVG
Mediocre 2.0

Pros: Nothing

Cons: Customer service

SFO
TAO
Excellent 8.0

Pros: I liked the foods serviced and kind crews. The flight departed on time. The atmosphere of cabin was quiet.

Cons: The services of the flight information and the slot of earphone was not working.

MNL
PVG
Excellent 10.0

Pros: amazing crew and nice boarding

Wed, 1 May
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
43h 05m
Sun, 5 May
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
35h 30m
S$ 1134
Trip: 5 days
Overall 0.0 Poor
Based on 0 reviews
Sun, 2 Jun
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
26h 30m
Mon, 17 Jun
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
40h 20m
S$ 1241
Trip: 16 days
6.5GoodShow reviews
Overall 6.5 Good
Based on 6,005 reviews
Overall
6.6
Boarding
6.7
Comfort
6.6
Crew
7.0
Entertainment
6.3
Food
6.1
DEL
PVG
Mediocre 2.3

Pros: Nothing! Couldn't be worse. The crew don't care about passengers and can't speak English either. We had a very long delay for no reason. The plane landed at a different airport that it was supposed to and then the airline bussed us to the Shanghai airport. Terrible terrible operation...

Cons: Everything! First please hire flight attendants that can speak English. Then provide better food. Even with Chinese standards the food had a bad quality. The stewardess didn't even understand that airplane mode exists for cell phones. She screamed at me to turn it off. Entertainment was a disaster

PVG
BKK
Mediocre 2.0

Cons: Hh

PVG
CGK
Mediocre 2.0

Cons: They did not let me on the plane due to my middle name not being on my passport. This have never happened to me before in all my years of travel. Worse yet, Kayak (JustFly) did not give me any refund or change my flight. It was "their policy." I will never use JustFly or China Eastern again.

BKK
PVG
Good 7.6

Cons: CE is budget carrier so you are often not walking into or out of terminal in China . You are on minibus commuting to/from plane. Once you land it may still be a 30-40 min commute to parking spot and minibus to terminal.

KIX
PVG
Good 7.0

Pros: It was a better experience (no screen that turns off and on by itself, no lopsided tray table) than my outbound flights, so kudos for that. The crew was very pleasant.

Cons: Food/snacks. I know people usually complain about airplane food, but I am not a picky eater and usually eat whatever is provided. I ended up picking at what was served. Perhaps I’m just not used to the selection since I usually fly American planes.

Thu, 18 Jul
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
21h 00m
Sun, 28 Jul
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
22h 30m
S$ 1399
Trip: 11 days
8.6ExcellentShow reviews
Overall 8.6 Excellent
Based on 5,335 reviews
Overall
8.7
Boarding
8.8
Comfort
8.5
Crew
8.9
Entertainment
8.4
Food
8.3
MFM
RMQ
Excellent 8.6

Cons: No IFE onboard these a321

SGN
TPE
Mediocre 2.0

Pros: Crew was rude and seat was very bad. I could not sleep

Cons: They could have been more nice and helpful

HKG
TPE
Excellent 9.3

Pros: I was late for my flight and the crew got me on standby for the next flight. No charges and no charge for checked bag. Exceptional customer service.

SIN
TPE
Excellent 8.0

Pros: Crews were very nice

Cons: Seat could have been a bit more comfortable and a little more leg room

FUK
TPE
Good 7.6

Pros: Crew was attentive and nice

Cons: More space for economy

Wed, 24 Apr
SIN
Singapore Changi
ORD
Chicago O'Hare Intl
47h 05m
Wed, 8 May
ORD
Chicago O'Hare Intl
SIN
Singapore Changi
23h 30m
S$ 1243
Trip: 15 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 25 Apr
SIN
Singapore Changi
MDW
Chicago Midway
24h 10m
Thu, 9 May
MDW
Chicago Midway
SIN
Singapore Changi
28h 45m
S$ 1899
Trip: 15 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
JFK
DEN
Good 7.2

Pros: Boarding was easy.

Cons: I am 6' 1" tall and weigh 220, so not out of the ordinary and I felt like I was stuffed into a sardine can.

SJU
JFK
Good 6.0

Cons: Was refused to use the 1st clas restrooms but 10 minutes layer the flight attendant allowed an older gentleman and a lady to use them. I was in 10A with my service dog

LAS
YYC
Mediocre 3.0

Pros: Seats were horrible, we all booked together and a bunch of my group got bumped to a different flight.

LGA
SRQ
Excellent 8.0

Pros: Didn’t like security. They were rude

Cons: Security

ATL
SFO
Excellent 10.0

Pros: Yes

Cons: Took off late. Other than that very comfortable and great experience

Thu, 2 May
SIN
Singapore Changi
MDW
Chicago Midway
41h 00m
Fri, 10 May
MDW
Chicago Midway
SIN
Singapore Changi
42h 00m
S$ 1483
Trip: 9 days
Overall 0.0 Poor
Based on 0 reviews
Thu, 5 Sep
SIN
Singapore Changi
MDW
Chicago Midway
29h 46m
Mon, 16 Sep
MDW
Chicago Midway
SIN
Singapore Changi
25h 23m
S$ 1901
Trip: 12 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
ATL
CRW
Excellent 9.0

Pros: The ctew was awesome, super sweet and very acomodating

Cons: Its a flight to WV (my birth place).... it is what it is... smll planes, tight quarters and people who don’t get any of that and are not happy anout any of it

LGA
MIA
Excellent 8.3

Pros: Crew was very attentive and friendly

Cons: Boarding could be better.

MCI
DTW
Excellent 8.0

Cons: If there could have been some sort of service at DTW to take customers to the gate of their connecting flight, for cases of really short time window of course, it’d be extremely helpful.

LIM
ATL
Excellent 9.2

Pros: Delta did a great job getting our checked bags from an overseas arrival to this flight. Boarding smooth.

Cons: Seats are cramped in coach. Fact of life for all carriers.

ANC
SEA
Excellent 9.3

Pros: Good service

Cons: Video system locked up at my seat

Fri, 19 Apr
SIN
Singapore Changi
MDW
Chicago Midway
25h 16m
Fri, 26 Apr
MDW
Chicago Midway
SIN
Singapore Changi
33h 46m
S$ 1903
Trip: 8 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
SYD
LAX
Excellent 10.0

Pros: Delta always does a superior job - domestically and internationally!

DCA
JFK
OK 4.0

Cons: Virgin Atlantic has had better days. Living off of a long gone reputation. Great staff but old and worn out planes. Code sharing has done them no favors!

YYZ
ATL
Excellent 9.6

Pros: I liked the touch screen displays in each headrest. Seats and leg room comfortable

Cons: Boarding was somewhat unorganized

LGA
SRQ
Excellent 8.0

Pros: Didn’t like security. They were rude

Cons: Security

LAS
YYC
Mediocre 3.0

Pros: Seats were horrible, we all booked together and a bunch of my group got bumped to a different flight.

Fri, 5 Jul
SIN
Singapore Changi
MDW
Chicago Midway
28h 12m
Sat, 20 Jul
MDW
Chicago Midway
SIN
Singapore Changi
25h 30m
S$ 1903
Trip: 16 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
AMS
BOS
Excellent 10.0

Pros: Good seating, great food, good service.

JFK
DEN
Good 7.2

Pros: Boarding was easy.

Cons: I am 6' 1" tall and weigh 220, so not out of the ordinary and I felt like I was stuffed into a sardine can.

ORD
LGA
Excellent 10.0

Pros: Flight attendant in first class was amazing.

BGR
LGA
OK 4.0

Cons: If it had left on time Waited 3 hours at the airport

YEG
MSP
Excellent 9.0

Pros: WiFi and Entertainment

Thu, 6 Jun
SIN
Singapore Changi
MDW
Chicago Midway
32h 32m
Mon, 17 Jun
MDW
Chicago Midway
SIN
Singapore Changi
35h 00m
S$ 1872
Trip: 12 days
Overall 0.0 Poor
Based on 0 reviews
Wed, 1 May
SIN
Singapore Changi
MDW
Chicago Midway
30h 50m
Tue, 7 May
MDW
Chicago Midway
SIN
Singapore Changi
25h 30m
S$ 2077
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
DUB
JFK
Excellent 8.0

Cons: The seats are not very comfortable for such a long flight

MSP
CVG
Excellent 10.0

Cons: No issues at all

MEM
MSP
Good 7.3

Cons: I booked a business class ticket through klm, but it was a delta code share flight. Delta was unable to locate me in their system, and I had to contact klm myself to straighten it out.

LAX
SYD
Good 7.6

Pros: The staff was friendly and helpful

Cons: Outlets to charge my electronic devices for the long flight

OAK
SLC
Excellent 10.0

Cons: Everything was excellent.

Thu, 1 Aug
SIN
Singapore Changi
MDW
Chicago Midway
29h 09m
Sun, 11 Aug
MDW
Chicago Midway
SIN
Singapore Changi
25h 30m
S$ 2274
Trip: 11 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 23,593 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.5
LAX
SYD
Good 7.6

Pros: The staff was friendly and helpful

Cons: Outlets to charge my electronic devices for the long flight

ATL
BOS
Good 6.6

Pros: Delta in flight entertainment is great.

Cons: Always delayed.

DEN
ATL
Good 7.0

Pros: Nothing spectacular.

Cons: The headrests won’t stay up. And it’s hot.

MCO
IND
Good 7.6

Pros: The flight timings and the arrival time

OAK
SLC
Excellent 10.0

Cons: Everything was excellent.

Show more results
*
Prices are per person, are for e–tickets and include all taxes & fees in SGD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car hires can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find on occasion that certain prices are no longer available.

More questions or if you have a bad price to report to us
Please send us an and someone from our team will get back to you promptly.