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Find cheap flights to Chicago from S$ 823

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 9-6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
sex 21-6
sex 28-6

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap flight deals to Chicago

 
These are the cheapest deals for flights to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent return flight deals to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Singapore to Chicago.

Recent one-way flight deals to Chicago

Only flying one-way? Below are some of the best one-way flight deals from Singapore to Chicago found on KAYAK recently.

Recent last-minute flight deals to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Singapore to Chicago.

Recent direct flight deals to Chicago

The latest deals for direct flights from Singapore to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals to Chicago

Find recent round-trip train or bus tickets from Singapore to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,334EVA Air
Find Deal
qui, 12 set - qui, 19 set
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,335EVA Air
Find Deal
qui, 12 set - dom, 22 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,409Air India
Find Deal
seg, 16 set - qua, 25 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,436Air India
Find Deal
sáb, 14 set - seg, 23 set
01:50 - 09:10SIN-ORD
20h 20m1 stop
12:05 - 06:15ORD-SIN
29h 10m1 stop
S$ 1,481Japan Airlines
Find Deal
qua, 11 set - seg, 23 set
11:05 - 15:10SIN-ORD
41h 05m1 stop
08:58 - 06:15ORD-SIN
32h 17m2 stops
S$ 1,496United Airlines
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qui, 12 set - seg, 23 set
01:50 - 09:10SIN-ORD
20h 20m1 stop
12:05 - 06:15ORD-SIN
29h 10m1 stop
S$ 1,512Japan Airlines
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ter, 10 set - ter, 24 set
08:45 - 00:45SIN-ORD
29h 00m1 stop
14:02 - 08:00ORD-SIN
27h 58m1 stop
S$ 1,715United Airlines
Find Deal
seg, 5 ago - qui, 16 jan
06:15 - 14:55SIN-ORD
21h 40m1 stop
07:30 - 00:45ORD-SIN
28h 15m2 stops
S$ 1,848ANA
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sex, 13 set - ter, 24 set
22:10 - 08:40SIN-ORD
23h 30m1 stop
07:30 - 00:45ORD-SIN
28h 15m2 stops
S$ 2,026ANA
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dom, 15 set - sex, 20 set
13:05 - 05:49SIN-ORD
53h 44m3 stops
S$ 823
Find Deal
dom, 9 jun
22:15 - 05:49SIN-ORD
44h 34m2 stops
S$ 882
Find Deal
dom, 9 jun
15:45 - 20:45SIN-ORD
42h 00m1 stop
S$ 893EVA Air
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ter, 29 out
13:10 - 21:00SIN-ORD
20h 50m1 stop
S$ 991EVA Air
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dom, 9 jun
23:25 - 12:15SIN-ORD
25h 50m1 stop
S$ 1,248Lufthansa
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sáb, 8 jun
01:50 - 00:16SIN-ORD
35h 26m2 stops
S$ 1,276Japan Airlines
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sáb, 22 jun
23:40 - 12:50SIN-ORD
26h 10m2 stops
S$ 1,296Lufthansa
Find Deal
dom, 28 jul
01:50 - 19:33SIN-ORD
30h 43m2 stops
S$ 1,420Japan Airlines
Find Deal
qui, 25 jul
23:35 - 07:25SIN-ORD
44h 50m1 stop
S$ 3,454Air India
Find Deal
sex, 20 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
S$ 4,561Air India
Find Deal
sáb, 27 jul
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,365EVA Air
Find Deal
seg, 27 mai - seg, 29 jul
21:50 - 19:38SIN-ORD
34h 48m2 stops
12:25 - 06:15ORD-SIN
28h 50m1 stop
S$ 1,625American Airlines
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seg, 27 mai - ter, 30 jul
21:50 - 17:10SIN-ORD
32h 20m2 stops
09:45 - 00:20ORD-SIN
25h 35m2 stops
S$ 1,628American Airlines
Find Deal
seg, 27 mai - ter, 30 jul
15:10 - 05:22SIN-ORD
27h 12m2 stops
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,675EVA Air
Find Deal
seg, 27 mai - seg, 29 jul
08:35 - 07:25SIN-ORD
35h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,691Air India
Find Deal
seg, 27 mai - ter, 30 jul
01:50 - 19:38SIN-ORD
30h 48m2 stops
12:25 - 17:35ORD-SIN
40h 10m1 stop
S$ 1,780American Airlines
Find Deal
dom, 26 mai - ter, 30 jul
01:50 - 19:38SIN-ORD
30h 48m2 stops
09:45 - 00:20ORD-SIN
25h 35m2 stops
S$ 1,783American Airlines
Find Deal
dom, 26 mai - ter, 30 jul
22:30 - 22:01SIN-MDW
36h 31m2 stops
06:00 - 23:40MDW-SIN
28h 40m2 stops
S$ 1,827Delta
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seg, 27 mai - ter, 30 jul
02:15 - 15:25SIN-ORD
26h 10m1 stop
19:40 - 20:45ORD-SIN
36h 05m1 stop
S$ 2,807Qatar Airways
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dom, 26 mai - ter, 30 jul
01:10 - 12:40SIN-MDW
24h 30m2 stops
09:33 - 23:40MDW-SIN
25h 07m2 stops
S$ 9,221Delta
Find Deal
dom, 26 mai - ter, 30 jul
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,334EVA Air
Find Deal
qui, 12 set - qui, 19 set
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,335EVA Air
Find Deal
qui, 12 set - dom, 22 set
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,365EVA Air
Find Deal
sáb, 21 set - sex, 27 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,409Air India
Find Deal
seg, 16 set - qua, 25 set
19:50 - 16:15SIN-ORD
33h 25m1 stop
17:25 - 05:40ORD-SIN
23h 15m1 stop
S$ 1,420Singapore Airlines
Find Deal
seg, 16 set - ter, 24 set
13:10 - 20:45SIN-ORD
20h 35m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,431EVA Air
Find Deal
qua, 11 set - sex, 20 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,436Air India
Find Deal
sáb, 14 set - seg, 23 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,444Air India
Find Deal
sáb, 14 set - qui, 26 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,459Air India
Find Deal
qua, 11 set - qua, 25 set
23:35 - 07:25SIN-ORD
44h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,467Air India
Find Deal
sáb, 21 set - sáb, 28 set

Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Monday where tickets can be as cheap as S$ 1,653. On the other hand, the most expensive day to fly is Thursday, where prices are S$ 2,478 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago is October, where tickets cost S$ 1,474 on average for one-way flights. On the other hand, the most expensive months are July and August, where the average cost of tickets from Singapore is S$ 2,419 and S$ 2,403 respectively. For return trips, the best month to travel is October with an average price of S$ 1,474.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally in the afternoon, when flights cost S$ 1,695 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is S$ 1,894.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 0 weeks before departure. For the absolute cheapest price, our data suggests you should book 88 days before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago O'Hare Intl Airport, with an average flight price of S$ 425.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 77% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Singapore, which takes 35h 50m.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 823
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Singapore to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • Which Chicago airport is closest to central Chicago?

    Out of the 3 airports in Chicago, Chicago Midway Airport is the nearest to the city center (14 km). You'll travel 26 km to reach the center of Chicago if you land in Chicago O'Hare Airport and 126 km if you land in Chicago Greater Rockford.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airline offers the most flights to Chicago?

    Of the 14 airlines that fly to Chicago, American Airlines offers the most flights, with around 4,255 per week, followed by United Airlines with 3,395 flights per week.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

Singapore to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights
See more direct flights

Top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Singapore to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.4
ANAOverall score based on 918 reviews
8.8Crew
8.3Comfort
8.6Boarding
7.8Food
8.0Entertainment
Airline reviews

Excellent. All the ticket prices have gone up so much. With only economy as the option, I thought I better pay for a good airline and I am glad I took ANA. The only thing is the long layover at Hanaeda enroute to Singapore. Any chance to bring back the service to land at Narita instead for the transit and a shorter layover will be fantastic. I am a fan of ANA.

10.0 ExcellentLay, May 2024IAD - HND
Read more about ANA reviews

Excellent. All the ticket prices have gone up so much. With only economy as the option, I thought I better pay for a good airline and I am glad I took ANA. The only thing is the long layover at Hanaeda enroute to Singapore. Any chance to bring back the service to land at Narita instead for the transit and a shorter layover will be fantastic. I am a fan of ANA.

Incredible. Amazing legroom. Over head fans for each person. Tv screens were great. Headphones were adequate. Seats were comfortable and spacious. Loved it.

I booked a ANA flight, this was just a regular United flight — as always very bad, dirty, rude service, quite frankly really embarrassing to be flying with this after spending time in Japan.

Staff and crew are wonderful, professional and courteous. Meal is delicious and snacks can be improved. Entertainment needs improvement, pls update selections of movies. I appreciate that our flight was on time

I flew economy class so of course it’s not as roomy as business and first class. But overall it was ok and the seat had an interesting way to recline — the seat itself extended forward instead of the backrest. This way the person sitting behind me would not lose space by my reclining—excellent concept. I wish all airlines used these seats.

Flying with ANA is always a breeze. Seats are very comfortable.

For the price of a seat that is obviously crammed together so as to get many more people onboard and combined with the long flight duration, Free WiFi should be an automatic “Thank You for Flying with Us!” To charge an additional fee when so many other businesses offers it is a bit “cheap” on the airline’s part.

Food was high quality. Crew was extremely professional, polite, attentive. Flights were on time. Plane had good media tech.

I wish the serve should leach and drink. Maybe because only 2hr

It was ok I thought because my flight was 1pm i was expecting to have lunch but it didn’t and after 7 hr finally dinner time was only chicken sandwich and next breakfast was an hour before plane land in Tokyo. so I should bring some food with me. Japanese flight attend was nice but the other was chewing gum and how she ask and respond to customers was not professional I felt. Maybe because Japan flight attendant is highly train and everyone looked very dress and professional so I was kind disappointed. I like that the bathroom was very clean .

The food was good, but we are not able to use earphones to watch a movie.

I was expecting that movie selection and food would have been better. Everything else was great.

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

The crew is so cold and indifferent but I have to appreciate their professionalism. The seat is too hard and not comfortable at all. Entertainment is very limited and not of many choices.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

I was feeling very comfortable throughout the flight. I got more leg room than I expected from a Y class seat. But the food was a little disappointing.

All of the JAL flights in this itinerary were great. However the last leg of my flight from LAX to SFO was through Japan Air’s partner, AA which wqsn’t up to par. We were informed only minutes before boarding time of a delay despite the airlines knowing about the delay far earlier (the aircraft we would be taking arriving arrived and disembarked close to our boarding time, for all to see but AA still kept the original boarding time posted until last minute). Furthermore, once we boarded the taxi/wait time was also extended, with the pilot blaming “construction at SFO” for the delay, rather than taking accountability for the the plane’s late arrival coming into LAX. We took off approximately an hour later than scheduled. It’s for these reasons I adamantly avoid American Airlines when possible. Again, JAL was stellar.

Great service but food taste and options have gone down a few notches.

This airlines is always my favorite. Very consistent customer service and food is good. My last flight with them, I had no idea we landed because it was just that smooth of a land.

At least it was not very cold inside the plane. I noticed there was now a bidet in the bathroom and that’s good! I didn’t like the window seat. Flight was smooth except for 1 turbulence. Plane was on time. Thanks. Food was not that great. Miso and green tea were good! As usual movies were old and there were no changes.

Food as always. PA was not clear, especially the English ones. Very limited Hollywood movies. Unlike the first flight I had, this plane has less leg room and less room for my under seat baggage.

Great crew, Japanese domestic flight is just a drink service but crew are very attentive

I didn’t like the check in process I had to check in at the counter took too much time . Didn’t give the upgrade my seat .

Japan airlines is excellent. I had a great flight with them, and they are the consummate professionals. I booked my flight through Kayak and they sent it on to Underpricer. That felt really scammy. My Oneworld number would not attach to the reservation and I could not choose a seat. I called Japan Airlines and got one but it was in the back. Later I drove to the airport and worked with the excellent agents there to find a better one. Later that day, I got a phone call from Underpricer trying to upsell me the option of choosing a seat. It felt like a Spirit Airlines level crappy move. The flight itself was exactly as nice as you would expect from JAL. The meal was good and the flight crew was awesome.

Good and movies are so old. Needs to have more up-to-date movies.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Very poor experience for the price paid. Airplane interior including seats were old and jaded. Seat tray table did not work properly. Head phone was defective and didn’t work. Food was mediocre

Communication was terrible. Flight was delayed for 4-5 hours in DC (on the front end, and also after we boarded, we had to get off - some issue with fueling the old plane correctly). There was little to no information on timing or what was happening. Once we reach Delhi airspace, apparently there was weather that caused us not to land - we were actually near the ground, saw the run way, and lifted back up to the sky after being sooo close. Then we circled for about 30 minutes, and they decided to go to Jaipur to land until the weather cleared and to refuel. Again, once we landed in Jaipur (wrong city), there was little to no information on timing or what was happening. Then we heard that the crew was reaching their 24 hours. We sat on the place, on the tarmac for another 3 HOURS, with no food and not enough water for everyone on the flight. Then, they kicked us off the plane with no plan, in the wrong city. We went thru customs, got our bags (thank goodness), and had to ask a bunch of staff what was happening and what to do. Eventually, their soltuion was to bus people back to Delhi (like 6 hours we were told) but not everyone would fit on the bus, and unknown timing on when it would leave. At this point it was 9PM (we were scheduled to arrive in Delhi at 11AM...). My husband and I decided to risk it and take a cab that we had to pay ourselves (about $200 US dollars) to get to Delhi (about 5 hour drive). We both had terrible trips back to the US as well - almost missed connecting flight, forced to pay for carry-on luggage (a small back pack!) and duty-free goods by the Air India staff last minute. Just terrible experience all around. Never again with AI! The ONLY good thing was the air hostesses were kind and patient - example: they made sure people with food allergies got their correct. However, the TV's did not work so I'm glad we brought our own entertainment.

The Air India lounge in Delhi , was very disappointing! The food was of poor quality and options were limited especially for vegetarians!! Beverages were fine. The in flight crew was excellent! . They helped me with my seat controls - the controls did not work without a hassle or assistance!! A very poor showing for a Business cabin!!! Post flight , the wheel chair passengers ( including Me) were “ shepherded and left waiting twice (an hour or more) before taking us to immigration! I chose to Fly Air India because I want. to patronize our National carrier with the hope that the experience will improve!!! Regrettably, I will have to look at other options for my next trip to India

Entertainment system was not working and was told I would get a voucher and have not got one. No toiletries were available not even a toothbrush false sweet talk by ground staff

Worst International flight I ever had in my whole life time. Boarding is the worst of all and flight experience was also not good. Screens were not working, seats were not comfortable and lot more.

Very very impressed with the proactive care and alertness with which ABHISHEK Chowdhary took care of us. Quietl,dignified , very alert, and meticulous. Very impressed. Also with SUNiL Kumar who was there for us in a very helpful way. SHERLY ALEX On Flight 119, BOM TO JFK CUSTOMER ON SEAT 21C, 21ST March 2024

If you are traveling to mumbai -- must try SFO - MUM direct flight. It's a game changer when you are traveling to India. Timings are well designed, optimal and makes the travel enjoyable.

Air India needs to launch new planes. Seats are worn out, most of the plane's TV screens wasn't working, USB charging ports wasn't working as well so I can charge my phone & watch my download movies, Food was mediocre, the plane smells. How can Air India put through their customers with this bad experience? This complaint needs to get escalated to the upper management. How shameful is the upper management to improve this plane? The flight is going back & forth from NEW YORK & DELHI. Two of the big cities in the world and this is how your experience is for sitting in a plane for 12+ hrs? Get your planes fixed ASAP Air India (TATA Management do your job right).

One of my worst experiences. Nothing was working in the flight. Entertainment system was broken, seat was very uncomfortable, crew did not offer water until food was provided, lights were not working, attendant call was not working. In short everything was broken and duct taped.

Old aircraft, crew were so so. Meals were mediocre. Flight to delhi was delayed. Lounge needs update and was mediocre too.

Book Cheap Chicago Plane Tickets

Recent return flight deals

 
These are the cheapest return flights to Chicago found on KAYAK in the last 72 hours.
12-9qui
1 stopEVA Air
20h 35mSIN-ORD
19-9qui
1 stopEVA Air
22h 30mORD-SIN
S$ 1,334
12-9qui
1 stopEVA Air
20h 35mSIN-ORD
22-9dom
1 stopEVA Air
22h 30mORD-SIN
S$ 1,335
16-9seg
1 stopAir India
44h 50mSIN-ORD
25-9qua
1 stopAir India
30h 30mORD-SIN
S$ 1,409
14-9sáb
1 stopAir India
44h 50mSIN-ORD
23-9seg
1 stopAir India
30h 30mORD-SIN
S$ 1,436
11-9qua
1 stopJapan Airlines
20h 20mSIN-ORD
23-9seg
1 stopJapan Airlines
29h 10mORD-SIN
S$ 1,481
12-9qui
1 stopUnited Airlines
41h 05mSIN-ORD
23-9seg
2 stopsUnited Airlines
32h 17mORD-SIN
S$ 1,496
10-9ter
1 stopJapan Airlines
20h 20mSIN-ORD
24-9ter
1 stopJapan Airlines
29h 10mORD-SIN
S$ 1,512
5-8seg
1 stopUnited Airlines
29h 00mSIN-ORD
16-1qui
1 stopUnited Airlines
27h 58mORD-SIN
S$ 1,715
13-9sex
1 stopANA
21h 40mSIN-ORD
24-9ter
2 stopsANA
28h 15mORD-SIN
S$ 1,848
15-9dom
1 stopANA
23h 30mSIN-ORD
20-9sex
2 stopsANA
28h 15mORD-SIN
S$ 2,026

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
9-6dom
3 stops
53h 44mSIN-ORD
S$ 823
9-6dom
2 stops
44h 34mSIN-ORD
S$ 882
29-10ter
1 stopEVA Air
42h 00mSIN-ORD
S$ 893
9-6dom
1 stopEVA Air
20h 50mSIN-ORD
S$ 991
8-6sáb
1 stopLufthansa
25h 50mSIN-ORD
S$ 1,248
22-6sáb
2 stopsJapan Airlines
35h 26mSIN-ORD
S$ 1,276
28-7dom
2 stopsLufthansa
26h 10mSIN-ORD
S$ 1,296
25-7qui
2 stopsJapan Airlines
30h 43mSIN-ORD
S$ 1,420
20-9sex
1 stopAir India
44h 50mSIN-ORD
S$ 3,454
27-7sáb
1 stopAir India
44h 50mSIN-ORD
S$ 4,561

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Recent domestic flight deals

16-6dom
directJetBlue
2h 54mBOS-ORD
20-6qui
directJetBlue
2h 26mORD-BOS
S$ 155
16-6dom
directJetBlue
2h 54mBOS-ORD
19-6qua
multi-stopJetBlue
8h 27mORD-BOS
S$ 167
18-6ter
directJetBlue
2h 43mJFK-ORD
25-6ter
directJetBlue
2h 20mORD-JFK
S$ 171
5-6qua
multi-stopSpirit Airlines
7h 40mEWR-ORD
5-6qua
multi-stopSpirit Airlines
13h 33mORD-EWR
S$ 183
18-6ter
directDelta
2h 44mJFK-ORD
9-7ter
directDelta
2h 16mORD-JFK
S$ 198
25-6ter
directDelta
2h 50mLGA-ORD
2-7ter
directDelta
2h 09mORD-LGA
S$ 198
5-6qua
directUnited Airlines
2h 38mLGA-ORD
6-6qui
directUnited Airlines
2h 21mORD-LGA
S$ 248
9-6dom
directUnited Airlines
2h 50mBOS-ORD
12-6qua
directUnited Airlines
2h 35mORD-BOS
S$ 274
20-6qui
multi-stopAmerican Airlines
13h 55mDCA-ORD
21-6sex
directAmerican Airlines
1h 47mORD-DCA
S$ 583
5-6qua
multi-stopAmerican Airlines
5h 00mLGA-ORD
6-6qui
multi-stopAmerican Airlines
3h 31mORD-LGA
S$ 584

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Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
27-5seg
multi-stopEVA Air
20h 50mSIN-ORD
29-7seg
multi-stopEVA Air
24h 20mORD-SIN
S$ 1,365
27-5seg
multi-stopAmerican Airlines
34h 48mSIN-ORD
30-7ter
multi-stopAmerican Airlines
28h 50mORD-SIN
S$ 1,625
27-5seg
multi-stopAmerican Airlines
32h 20mSIN-ORD
30-7ter
multi-stopAmerican Airlines
25h 35mORD-SIN
S$ 1,628
27-5seg
multi-stopEVA Air
27h 12mSIN-ORD
29-7seg
multi-stopEVA Air
24h 20mORD-SIN
S$ 1,675
27-5seg
multi-stopAir India
35h 50mSIN-ORD
30-7ter
multi-stopAir India
30h 30mORD-SIN
S$ 1,691
26-5dom
multi-stopAmerican Airlines
30h 48mSIN-ORD
30-7ter
multi-stopAmerican Airlines
40h 10mORD-SIN
S$ 1,780
26-5dom
multi-stopAmerican Airlines
30h 48mSIN-ORD
30-7ter
multi-stopAmerican Airlines
25h 35mORD-SIN
S$ 1,783
27-5seg
multi-stopDelta
36h 31mSIN-MDW
30-7ter
multi-stopDelta
28h 40mMDW-SIN
S$ 1,827
26-5dom
multi-stopQatar Airways
26h 10mSIN-ORD
30-7ter
multi-stopQatar Airways
36h 05mORD-SIN
S$ 2,807
26-5dom
multi-stopDelta
24h 30mSIN-MDW
30-7ter
multi-stopDelta
25h 07mMDW-SIN
S$ 9,221

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Flights to Chicago

Return flight deals:

Chicago - Singapore

Cabin classes: