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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 10-5. 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
Thu 18-4
Thu 25-4

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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
In the last 7 days, travellers have searched 47,600,107 times on KAYAK, and here's why:

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Cheap flight deals to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
01:50 - 00:14SIN-ORD
35h 24m2 stops
12:25 - 06:15ORD-SIN
28h 50m1 stop
S$ 1,325Japan Airlines
Find Deal
Tue, 25 Jun - Wed, 10 Jul
21:50 - 19:37SIN-ORD
34h 47m2 stops
12:25 - 06:15ORD-SIN
28h 50m1 stop
S$ 1,361Japan Airlines
Find Deal
Wed, 26 Jun - Wed, 10 Jul
08:35 - 07:25SIN-ORD
35h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,479Air India
Find Deal
Mon, 27 May - Wed, 31 Jul
08:35 - 07:25SIN-ORD
35h 50m1 stop
12:00 - 07:30ORD-SIN
30h 30m1 stop
S$ 1,531Air India
Find Deal
Mon, 27 May - Wed, 31 Jul
21:00 - 16:55SIN-ORD
32h 55m2 stops
21:45 - 18:45ORD-SIN
32h 00m1 stop
S$ 1,650United Airlines
Find Deal
Sat, 20 Apr - Sun, 12 May
21:00 - 05:47SIN-ORD
21h 47m1 stop
07:10 - 18:45ORD-SIN
22h 35m1 stop
S$ 1,702United Airlines
Find Deal
Mon, 27 May - Thu, 1 Aug
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,772EVA Air
Find Deal
Sat, 25 May - Sun, 28 Jul
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,777EVA Air
Find Deal
Tue, 28 May - Mon, 29 Jul
06:15 - 14:55SIN-ORD
21h 40m1 stop
07:10 - 00:45ORD-SIN
28h 35m2 stops
S$ 1,787ANA
Find Deal
Thu, 25 Apr - Wed, 1 May
06:15 - 14:55SIN-ORD
21h 40m1 stop
07:10 - 00:45ORD-SIN
28h 35m2 stops
S$ 1,967ANA
Find Deal
Thu, 25 Apr - Mon, 29 Apr

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$ 1,685. On the other hand, the most expensive day to fly is Friday, where prices are S$ 1,791 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$ 1,464 on average for one-way flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Singapore is S$ 2,330 and S$ 2,279 respectively. For return trips, the best month to travel is October with an average price of S$ 1,464.

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$ 1,715 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$ 2,001.

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 44 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$ 564.

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 78% 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 24h 20m.

How many long-haul flights are there to Chicago each week?

Each week there are around 521 long-haul flights (6-12 hour flight duration), 1,252 medium-haul (3-6 hour flight duration) and 12,883 short-haul (up to 3 hour flight duration) flights to Chicago. The most long-haul flights depart from London.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 823
Best time to beat the crowds (6% less expensive on average)
Most popular time to fly and prices are also 6% lower on average.
Flight from Singapore to Chicago Midway 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 13 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,490 per week, followed by American Airlines with 4,350 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, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights

Direct returns

Chicago to Singapore

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Saturday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

Top 5 airlines flying to Chicago

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 KAYAK reviews.
8.4
ANAOverall score based on 998 reviews
86boarding
80entertainment
88crew
83comfort
78food
85overall
Airline reviews

This is a very long flight and the first time I have flown on a Japanese airline. I was very impressed with the staff. They worked hard and offered food and drink regularly. Plane was very well cared for. The let room was good . Food was ok but better than other airlines.

Read more about ANA

This is a very long flight and the first time I have flown on a Japanese airline. I was very impressed with the staff. They worked hard and offered food and drink regularly. Plane was very well cared for. The let room was good . Food was ok but better than other airlines.

It was very nice. I was a bit disappointed by the few meal services. There were probably more drink services that I missed while sleeping, but I would have liked the crew to bring more than one drink service before landing and to bring more than one drink service and coffee service after take off

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

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 .

Seat was roomy enough . The Asian selection for a meal was good . The tortellini was not very good. Service was excellent. O

It was very good. Lots of room with superior food and service. I will not hesitate to fly ANA in the future!

Lovely airport at Haneda. Great food selection. Spacious and private boarding area with dedicated bathroom for each gate.

They did not get my request for veg food that i made a month ago. Also did not have any backup veg food on board or fruit plate or simething. Very disappointing as i had hward about how grwat ANA was supossed to be. Alsio entertainment was lacking and screen and tech was subpar. Overall just mid to low tie. They are living off reputation and are being passed up by most other carriers.

Ana is absolute world class They should not work with united

Japan and China airlines were incredible. On board service was impeccable. All the flight attendants were helpful, friendly, and always smiling. Airplanes were very clean. The boarding crew was extremely accommodating and very nice as well. Overall I was extremely impressed.

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 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.

Polite hard working crew. No complaints really. Meals were not to my liking.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

t and I Flight crew did excellent job taking care of us and feeding us and staying professional. The boarding was delayed by an hour and then extra security measures were taken. No real explanation except for they said it was more of a maintenance dey

The flight was on time. Boarding process was smooth. The crew was friendly, helpful, and they kept plane facility clean. The food could've been better.

On time. Easy online check-in. But always give me a middle economy seat with wacky passengers (or even a seat next to the toilet room). Also could be more courtier staff.

wanted hindi vegetarian meal but that as a no-go

Liked the food. Needs improvement: 1) the flat bed was very hard and the set up was not at all passenger friendly 2) the announcement were impossible to understand even in English. 3) the flight information on the monitor was terrible it showed a airplane with no information like altitude, airspeed, heading. You could not zoom in or out to orient the aircraft to where you were in the flight. 4) movies were old and very limited as was the music selection.

It was one of the best experiences. The staff were amazing. JAL is my second favorite Asian Carrier I have flown on. Korean Air was my first. Thank you JAL for bringing me home safely and for such an amazing staff and service.

JAL is quite nice in business class. Comfortable, spacious seats. Their entertainment, especially their film selection, isn’t that great though as their are not many new releases like some airlines offer their first and business class customers. . Food is excellent and the option to order on demand is always quite nice, which JAL offers. Flight attendants were very friendly and kind. Overall very good experience with JAL.

Very comfortable unlike my first trip where they switched my flight from JAL to AA which was a disaster!

It was an outstanding flight and service. The only thing is the seat cushion for economy could be a little more comfortable. More cushion.

Movie dis not play smoothly. During play, it was interrupted several times, and could not RESUME where I was.

I requested a vegetarian meal, and somehow that wasn’t processed from Japan airlines to the new carrier American Airlines when it was on the ticket. Don’t know if that was KAYAK or Japan air or American Airlines. But the crew scrounge together something for me and that was very good. Also I think American has the tiniest seats in the industry. It’s kind of annoying but it got me from .8 point B and now I’m at point B on the final point at LAX. I had to leave the airport and then go back through security to catch my next plane. I’ve never had to do that before. It was very annoying.

I hope they never ran out of the menu choice one makes. They often do.

I was not given any food boats the times the entire flight. I had to go hungry for 10 hours the first flight and 12 hours the second one. They said they did not receive my special request for a vegetarian meal and they were very rude about it. I’m vegetarian because of religious reasons. I will never fly Japanese airlines ever again. And I really hope you are able to give me some compensation for this issue that was cars to me since you were also a Party to this whole transaction.

serving nuts is great, but it would be even better if it was overnight roasted nuts.

Unfortunately this is not a happy ending comment. Positive: flown United before no issue Negative: it only takes one bad experience to not plan future travel with United Cancún departure was delayed by 1h20 minutes, connection in Chicago was 1h30 minutes. Flight departure time 6:08 Miraculously 7 of us ran 4 kilometres through Chicago to arrive at 6:00 to be told very rudely by the 2 unprofessional United attendants you missed your flight and that we should of arrived early. Did I mention that reason I was flying? I received a call that my brother was dying and to get home. They provided no assistance would not answer any of our questions, ignorantly walked away. Deplorable

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

If United expects people to use their own devices for entertainment they should put charging outlets in each seating area. I arrived with 14%battery power. That is not good when you arrive anywhere and need to communicate for transportation.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

Great crew, friendly. Found the trip long just sitting with no onboard entertainment

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Liked the excellent United crew, the food selection, the comfortable cabin and the excellent movie and tv shows selection. The interface on the screen is also excellent and gives the option to let the crew know to wake you up for meals, or not. I disliked the onboarding experience at the Brussels airport. The process is convoluted and was not explained to any passengers. I also don't understand why thee is an additional security screening when getting off the plane from Africa, when there was none when getting off the plane from the US.

Friendly flight crew, clean plane, on time, great tandoori chicken

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

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.

Bathrooms were horrible and no cleaning. Announced baggage claim carousel as one but came to a different one. People were waiting

Every thing was so old…. Can’t believe they are able to charge so much for this terrible level of service will use alternate company in future for all travel needs

The food on board the flight was atrocious - tasteless, spicy as hell, and simply a hodge podge of nonsensical items of poor quality.

The crew smile nicely when you board and exit, in between they are sullen and innattentive

Air India business class flight seat is too low and very congested I am 72 years old . I had knee surgery.Bcz seat was very low and there is nothing to hold near the seat when we sr citizens are going for washroom. For sr citizens one small handle should be there so that we can hold and getup.I reached on 29 th of Jan in US but still I have pain and swelling in my knee and severe back pain .Please do the needful Thank you 🙏

I liked the timing but rest all were bad like below: 1. No restroom and food in waiting area at gate before boarding the flight. There was 2nd security scan at gate C2 and if someone goes to restroom which was outside that gate have to again go through security. So not having restroom, water in waiting area I felt is a blunder. 2. Entertainment system was not working for many passengers including mine. Crew members told about issue not fixed on time hence 16+ hours was tough to spend. 3. Food in domestic Air India flight was better but in international flight it’s not good.

Better entertainment choices and better food required. Mediocre as compared to other airlines. Planes are old and need revamping

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.
25-6Tue
2 stopsJapan Airlines
35h 24mSIN-ORD
10-7Wed
1 stopJapan Airlines
28h 50mORD-SIN
S$ 1,325
26-6Wed
2 stopsJapan Airlines
34h 47mSIN-ORD
10-7Wed
1 stopJapan Airlines
28h 50mORD-SIN
S$ 1,361
27-5Mon
1 stopAir India
35h 50mSIN-ORD
31-7Wed
1 stopAir India
30h 30mORD-SIN
S$ 1,479
27-5Mon
1 stopAir India
35h 50mSIN-ORD
31-7Wed
1 stopAir India
30h 30mORD-SIN
S$ 1,531
20-4Sat
2 stopsUnited Airlines
32h 55mSIN-ORD
12-5Sun
1 stopUnited Airlines
32h 00mORD-SIN
S$ 1,650
27-5Mon
1 stopUnited Airlines
21h 47mSIN-ORD
1-8Thu
1 stopUnited Airlines
22h 35mORD-SIN
S$ 1,702
25-5Sat
1 stopEVA Air
20h 50mSIN-ORD
28-7Sun
1 stopEVA Air
24h 20mORD-SIN
S$ 1,772
28-5Tue
1 stopEVA Air
20h 50mSIN-ORD
29-7Mon
1 stopEVA Air
22h 30mORD-SIN
S$ 1,777
25-4Thu
1 stopANA
21h 40mSIN-ORD
1-5Wed
2 stopsANA
28h 35mORD-SIN
S$ 1,787
25-4Thu
1 stopANA
21h 40mSIN-ORD
29-4Mon
2 stopsANA
28h 35mORD-SIN
S$ 1,967

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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.
10-5Fri
3 stops
49h 27mSIN-MDW
S$ 823
10-5Fri
3 stops
49h 27mSIN-MDW
S$ 830
10-5Fri
3 stops
48h 43mSIN-ORD
S$ 847
2-9Mon
3 stops
44h 30mSIN-ORD
S$ 851
9-5Thu
3 stops
58h 09mSIN-MDW
S$ 899
7-5Tue
1 stopJapan Airlines
20h 30mSIN-ORD
S$ 1,246
7-5Tue
2 stopsJapan Airlines
34h 38mSIN-ORD
S$ 1,261
1-8Thu
1 stopLufthansa
37h 10mSIN-ORD
S$ 1,353
25-6Tue
1 stopEVA Air
20h 50mSIN-ORD
S$ 2,022
24-4Wed
1 stopAir India
35h 50mSIN-ORD
S$ 3,528

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Search by price

Recent domestic flight deals

14-5Tue
directSpirit Airlines
2h 39mLGA-ORD
14-5Tue
directSpirit Airlines
2h 11mORD-LGA
S$ 82
7-5Tue
directSpirit Airlines
2h 40mLGA-ORD
8-5Wed
directSpirit Airlines
2h 11mORD-LGA
S$ 95
29-4Mon
directAlaska Airlines
3h 59mSEA-ORD
30-4Tue
directAlaska Airlines
4h 34mORD-SEA
S$ 149
27-4Sat
directAlaska Airlines
4h 10mSEA-ORD
30-4Tue
directAlaska Airlines
4h 34mORD-SEA
S$ 155
17-4Wed
directSouthwest
2h 10mBWI-ORD
24-4Wed
directSouthwest
1h 50mORD-BWI
S$ 161
17-4Wed
multi-stopSouthwest
7h 30mBWI-ORD
24-4Wed
directSouthwest
1h 50mORD-BWI
S$ 220
17-4Wed
directUnited Airlines
2h 15mDCA-ORD
24-4Wed
directUnited Airlines
1h 55mORD-DCA
S$ 249
27-4Sat
directUnited Airlines
2h 15mBWI-ORD
28-4Sun
directUnited Airlines
1h 56mORD-BWI
S$ 280
11-4Thu
multi-stopAmerican Airlines
6h 48mBOS-ORD
12-4Fri
directAmerican Airlines
2h 26mORD-BOS
S$ 503
1-4Mon
directAmerican Airlines
2h 16mDCA-ORD
1-4Mon
multi-stopAmerican Airlines
15h 34mORD-DCA
S$ 566

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Flights to Chicago

Return flight deals:

Chicago - Singapore

Cabin classes: