S$ 770 Find cheap flights to Chicago

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 27-11. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
In the last 7 days, travellers have searched 47,107,125 times on KAYAK, and here's why:

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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
10:50 - 09:50SIN-ORD
36h 00m1 stop
12:20 - 19:55ORD-SIN
42h 35m1 stop
S$ 1,297Korean Air
Find Deal
Sun, 13 Apr - Sun, 4 May
01:10 - 09:50SIN-ORD
21h 40m1 stop
12:20 - 05:00ORD-SIN
27h 40m1 stop
S$ 1,300Korean Air
Find Deal
Sat, 12 Apr - Sun, 4 May
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,431EVA Air
Find Deal
Mon, 14 Apr - Sun, 4 May
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,463EVA Air
Find Deal
Sun, 13 Apr - Sat, 3 May
10:45 - 15:05SIN-ORD
42h 20m1 stop
20:25 - 20:15ORD-SIN
33h 50m1 stop
S$ 1,480United Airlines
Find Deal
Mon, 13 Jan - Thu, 16 Jan
10:45 - 06:16SIN-ORD
33h 31m2 stops
06:30 - 20:15ORD-SIN
23h 45m1 stop
S$ 1,486United Airlines
Find Deal
Mon, 13 Jan - Thu, 16 Jan
01:45 - 14:25SIN-ORD
25h 40m1 stop
16:05 - 11:55ORD-SIN
30h 50m1 stop
S$ 1,533Cathay Pacific
Find Deal
Sun, 13 Apr - Mon, 5 May
02:20 - 17:45SIN-ORD
29h 25m2 stops
10:35 - 06:40ORD-SIN
30h 05m1 stop
S$ 1,620Japan Airlines
Find Deal
Sun, 12 Jan - Thu, 16 Jan
02:20 - 17:45SIN-ORD
29h 25m2 stops
07:18 - 00:50ORD-SIN
27h 32m2 stops
S$ 1,887Japan Airlines
Find Deal
Sun, 12 Jan - Thu, 16 Jan
01:25 - 13:00SIN-ORD
25h 35m1 stop
14:40 - 13:05ORD-SIN
32h 25m1 stop
S$ 1,968Cathay Pacific
Find Deal
Sun, 12 Jan - Thu, 16 Jan
19:40 - 18:25SIN-ORD
36h 45m2 stops
S$ 770IndiGo
Find Deal
Wed, 27 Nov
00:40 - 23:20SIN-MDW
36h 40m3 stops
S$ 852
Find Deal
Mon, 23 Dec
23:25 - 10:10SIN-ORD
24h 45m1 stop
S$ 883Turkish Airlines
Find Deal
Wed, 29 Jan
13:15 - 19:35SIN-ORD
20h 20m1 stop
S$ 927EVA Air
Find Deal
Fri, 27 Dec
20:15 - 13:00SIN-ORD
30h 45m1 stop
S$ 968Cathay Pacific
Find Deal
Sat, 21 Dec
01:25 - 13:00SIN-ORD
25h 35m1 stop
S$ 974Cathay Pacific
Find Deal
Thu, 26 Dec
13:15 - 19:35SIN-ORD
20h 20m1 stop
S$ 1,005EVA Air
Find Deal
Fri, 17 Jan
02:20 - 07:35SIN-ORD
19h 15m1 stop
S$ 1,386Japan Airlines
Find Deal
Thu, 16 Jan
02:20 - 07:35SIN-ORD
19h 15m1 stop
S$ 1,388Japan Airlines
Find Deal
Thu, 16 Jan
10:10 - 05:25SIN-ORD
33h 15m3 stops
S$ 1,926United Airlines
Find Deal
Fri, 17 Jan
23:45 - 18:25SIN-ORD
32h 40m1 stop
18:00 - 17:05ORD-SIN
33h 05m1 stop
S$ 1,607Lufthansa
Find Deal
Sat, 23 Nov - Tue, 3 Dec
23:45 - 12:15SIN-ORD
26h 30m2 stops
18:00 - 17:05ORD-SIN
33h 05m1 stop
S$ 1,639Lufthansa
Find Deal
Sat, 23 Nov - Tue, 3 Dec
10:10 - 20:23SIN-ORD
24h 13m2 stops
16:05 - 08:00ORD-SIN
25h 55m2 stops
S$ 1,653United Airlines
Find Deal
Sat, 23 Nov - Tue, 3 Dec
01:25 - 13:00SIN-ORD
25h 35m1 stop
11:05 - 05:00ORD-SIN
27h 55m1 stop
S$ 1,846
Find Deal
Fri, 22 Nov - Tue, 3 Dec
01:25 - 13:00SIN-ORD
25h 35m1 stop
09:00 - 00:50ORD-SIN
49h 50m2 stops
S$ 1,898
Find Deal
Fri, 22 Nov - Tue, 3 Dec
01:30 - 23:58SIN-ORD
36h 28m2 stops
07:05 - 05:00ORD-SIN
31h 55m2 stops
S$ 2,726Delta
Find Deal
Fri, 22 Nov - Tue, 3 Dec
01:30 - 21:46SIN-MDW
34h 16m2 stops
19:17 - 00:10MDW-SIN
38h 53m2 stops
S$ 3,477Delta
Find Deal
Fri, 22 Nov - Tue, 3 Dec
23:55 - 18:55SIN-ORD
33h 00m2 stops
08:48 - 21:55ORD-SIN
47h 07m3 stops
S$ 4,266Air China
Find Deal
Sat, 23 Nov - Tue, 3 Dec
11:00 - 21:46SIN-MDW
24h 46m2 stops
19:17 - 00:10MDW-SIN
38h 53m2 stops
S$ 6,373Delta
Find Deal
Sat, 23 Nov - Tue, 3 Dec
10:50 - 09:50SIN-ORD
36h 00m1 stop
12:20 - 19:55ORD-SIN
42h 35m1 stop
S$ 1,297Korean Air
Find Deal
Sun, 13 Apr - Sun, 4 May
01:10 - 09:50SIN-ORD
21h 40m1 stop
12:20 - 05:00ORD-SIN
27h 40m1 stop
S$ 1,300Korean Air
Find Deal
Sat, 12 Apr - Sun, 4 May
23:10 - 17:55SIN-ORD
31h 45m1 stop
19:50 - 07:55ORD-SIN
23h 05m1 stop
S$ 1,348Turkish Airlines
Find Deal
Mon, 14 Apr - Mon, 5 May
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 13:50ORD-SIN
24h 20m1 stop
S$ 1,431EVA Air
Find Deal
Mon, 14 Apr - Sun, 4 May
13:10 - 21:00SIN-ORD
20h 50m1 stop
18:50 - 12:00ORD-SIN
28h 10m2 stops
S$ 1,450
Find Deal
Mon, 14 Apr - Mon, 5 May
13:10 - 21:00SIN-ORD
20h 50m1 stop
00:30 - 12:00ORD-SIN
22h 30m1 stop
S$ 1,463EVA Air
Find Deal
Sun, 13 Apr - Sat, 3 May
10:45 - 15:05SIN-ORD
42h 20m1 stop
20:25 - 20:15ORD-SIN
33h 50m1 stop
S$ 1,480United Airlines
Find Deal
Mon, 13 Jan - Thu, 16 Jan
10:45 - 06:16SIN-ORD
33h 31m2 stops
06:30 - 20:15ORD-SIN
23h 45m1 stop
S$ 1,486United Airlines
Find Deal
Mon, 13 Jan - Thu, 16 Jan
01:10 - 09:50SIN-ORD
21h 40m1 stop
06:20 - 05:00ORD-SIN
33h 40m2 stops
S$ 1,489Delta
Find Deal
Sat, 12 Apr - Sun, 4 May
01:10 - 23:53SIN-ORD
35h 43m2 stops
18:50 - 23:40ORD-SIN
39h 50m2 stops
S$ 1,493Delta
Find Deal
Sun, 13 Apr - Mon, 5 May

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 Thursday where tickets can be as cheap as S$ 1,609. On the other hand, the most expensive day to fly is Sunday, where prices are S$ 2,359 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$ 1,437 on average for one-way flights. On the other hand, the most expensive months are August and June, where the average cost of tickets from Singapore is S$ 2,001 and S$ 1,907 respectively. For return trips, the best month to travel is October with an average price of S$ 1,437.

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$ 1,522 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$ 1,734.

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 63 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$ 558.

Good to know

Low season

January

High season

May

Cheapest flight

S$ 770
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly (3% more expensive 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.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be July, August and September. The cheapest month to fly from Singapore is October.
  • 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, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 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, Aeromexico, +77 more

ANA, Aer Lingus, +78 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, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +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
EVA AirOverall score based on 1308 reviews
8.4Boarding
8.0Entertainment
8.0Food
8.6Crew
8.2Comfort
Airline reviews

The staff was marvelous. The entertainment options were terrible, old or 2nd rate movies. I was unable to entertain myself for 18 hours-it made it seem even longer. Note: I thought about upgrading but your information about what was included was unclear. Are the seats bigger? Are there current moves? What kind of food do you get? Would the upgrade compare to Delta? Just saying the upgrade is better didn’t convince me and I regret not flying Delta.

6.0 GoodMargaret, Nov 2024TPE - SFO
Read more EVA Air reviews

The staff was marvelous. The entertainment options were terrible, old or 2nd rate movies. I was unable to entertain myself for 18 hours-it made it seem even longer. Note: I thought about upgrading but your information about what was included was unclear. Are the seats bigger? Are there current moves? What kind of food do you get? Would the upgrade compare to Delta? Just saying the upgrade is better didn’t convince me and I regret not flying Delta.

Plane is new and I was upgraded to first class so all was great.

The flight from Taipei to LAX was the first time we encountered rudeness from the crew. From the gate agents to the in flight crew. We had received such wonderful service going to Bali and on our Bali to Taipei flight that it shocked us when the gate agent was rude and then the rudeness continued on the flight to LAX.

Overall great experience. All four members of my family were seated together without paying extra to reserve seats. Everything was on time. Food was great and healthy. Media entertainment was good. Rock music could be added as a listening choice. No issue with baggages. Flight attendants were friendly and helpful. I would recommend EVA to friends and family.

The crew was very helpful. Food was prepared with great care and tasted wonderful. Movie selection was a bit limited. The bedding on the seat is a little too thin for sleeping.

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

Their announcement was not quite clear in Chinese. The rest is pretty good.

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

On time. Great service. Good food. Good movies. All good!

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.

I ask the crew to help me get my bag because I can't reached it she ignore me

ANA’s service was great, and the flight was nice and smooth . They gave us updates and checking in and boarding was smooth and easy .

I have never been a big fan of airplane meals

Flight was overall OK: lovely staff and smooth travelling. The only downside was no food was available on a 3.5 hour flight over lunchtime. Luckily we had realised this in advance and brought our own bento.

Crew went out of their way for me, not often

Domestic flight, 1hr 20mins from SFO to LAX, which takes about probably 40-30mins on air.

Easy if you are a United States Citizen, when you go to US Border & Customs, bring your Passport if you arrive Internationally. Remember to pick up your check baggage before moving into domestic flights, as they will check the tag for the plane you are boarding in. (They will check your baggage again). Bring your ID/DL (Real-ID COMPLIANT) with you to pass security/TSA, passport works too. SFO is pretty strict as well as LAX. Domestic flight, 1hr 20mins from SFO to LAX, which takes about probably 40-30mins on air.

The seats are too small for international flights. I felt like cattle.

As my first experience in business class it was a great trip considering how long the flight is and how hard it usually is to sleep in economy

Crew was professional. Never enough leg room for 12 hour overnight flight.

Courteous and helpful employees. Comfortable seats and temperature of aircraft . Did not need squid in my salad but glad to have the menu information advising me of what it was

Everything was great, except the Wifi, but that's understandable.

The plane was dirty, there was trash in the seat pocket in front of me.

Food was excellent, the crew was exceptionally friendly, and the seats were comfortable. Bathroom were also kept very clean and odor free.

They woke us up 2.5 hours before the flight was over? Why? If I'm on a long haul flight I want to sleep as much as possible. Also, didn't mention the mattress pads in business class so missed out on using those. The western meal of truffle, salmon pasta was the awful. Had a different fish dish on JAL that was great but that pasta was a mish-mash of too many random things that didn't make sense plus dry fish. Staff was friendly and helpful.

I loved Ryuichi Sakamoto's OPUS in the movie choice.

Too bad the plane didn't work after we taxied out to get in line for take-off. We went back to the gate and waited for almost 90 minutes for them to find a plane that worked. Waited another hour to board. When we got to Rochester we waited for over an hour for our bags to appear. The agent said they only had three people working to load and unload baggage. A one hour flight took an extra four hours. It would have been faster to rent a car at JFK and drive to Rochester.

One of the best economy flights I’ve ever taken .

Good legroom. Front seatback has best compartmentalization, netted pockets on sides of tv monitor for eyeglasses, water bottles etc. For Economy, best food across the Pacific. JAL doesn't skimp on quality to squeeze out more profit. No prepackaged items in plastic wrap. Cocktail service first with nibbles, Wine in your own 2 glass bottle. Later dinner service, more wine! Lastly, breakfast-lunch, more wine if you choose. Lastly, the friendliest most smiling crew across the Pacific.

bag dropped took over an hour. there was only one agent behind the counter. Definitely need improvements on food! crews were very pleasant n helpful

bad… no veg food was provided eventhough i pre ordered special meal

Excellent service provided the flight crew. Food and drinks were very good.

Cathay has a great reputation, though it's baseline economy seating is nothing to write home about (and SE Asia flight passengers sometime lack 'routine stateside' etiquette). On the other hand, food was great, flight attendants were nice, and price was very good~

Cathay was not the problem. The problem was the customer service from Kayak/Underprice. Will never book through Kayak again.

The crews were smiling all the time with soft tunes when they spoke; the food was excellent. Thank you!

Cathay flight was fine, Amsterdam airport was a nightmare, spent way too much time walking to our next connection, no travelators.

They charged me $900 to board my flight I already paid for just because I missed my previous flight. I do not recommend this airline by any means.

Not good. Small seats. Not enough food that customers wanted. No special requests were given that i could see. Slow response from flight attendants

For a transpacific flight, flying economy is awful! The seats are cramped and its meant for petite folks! Good luck if you have long legs. BOARDING - AWFUL, we got to Hong Kong - the gate was listed, but upon arrival, there was a MESS of boarding procedures, they basically DIY'ed how to board but making three lines and putting three ground crew to check for passports in the terminal area. THEN to make it worse, after going through that cattle process, all of a sudden you see people standing and looking confused, apparently we were told to get in line to board, but the AV notification wasnt even working. So people started cramming in line - worse than cattle. One saving point, the flight crew forgot to serve me dinner and after waiting for it, I fell asleep since this was a midnight flight. After letting a crew know that I was forgotten, all of my meals were served first !!! Yay for being in the economy seats! Nothing much to write home about once more!

Bathroom was not cleaned as often as other airlines does. It was gross for a less than full flight capacity.

They canceled our flight and left us stranded to figure it out

We appreciated the friendly, efficient, and professional flight attendants. A wider selection of hot foods would be nice.

Did not have enough time from Venice seaport at Ravenna to get to Venice airport in order to make the scheduled flights. Need to have at least 3+ hours from ship docking to airport.

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

The plane used to go to Chicago was a bit outdated and needed a refresh

My connecting gate in .Chicago was across the aisle from my arriving gate. Otherwise I would not have made my connection. So that was very fortunate.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

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.
13-4Sun
1 stopKorean Air
36h 00mSIN-ORD
4-5Sun
1 stopKorean Air
42h 35mORD-SIN
S$ 1,297
12-4Sat
1 stopKorean Air
21h 40mSIN-ORD
4-5Sun
1 stopKorean Air
27h 40mORD-SIN
S$ 1,300
14-4Mon
1 stopEVA Air
20h 50mSIN-ORD
4-5Sun
1 stopEVA Air
24h 20mORD-SIN
S$ 1,431
13-4Sun
1 stopEVA Air
20h 50mSIN-ORD
3-5Sat
1 stopEVA Air
22h 30mORD-SIN
S$ 1,463
13-1Mon
1 stopUnited Airlines
42h 20mSIN-ORD
16-1Thu
1 stopUnited Airlines
33h 50mORD-SIN
S$ 1,480
13-1Mon
2 stopsUnited Airlines
33h 31mSIN-ORD
16-1Thu
1 stopUnited Airlines
23h 45mORD-SIN
S$ 1,486
13-4Sun
1 stopCathay Pacific
25h 40mSIN-ORD
5-5Mon
1 stopCathay Pacific
30h 50mORD-SIN
S$ 1,533
12-1Sun
2 stopsJapan Airlines
29h 25mSIN-ORD
16-1Thu
1 stopJapan Airlines
30h 05mORD-SIN
S$ 1,620
12-1Sun
2 stopsJapan Airlines
29h 25mSIN-ORD
16-1Thu
2 stopsJapan Airlines
27h 32mORD-SIN
S$ 1,887
12-1Sun
1 stopCathay Pacific
25h 35mSIN-ORD
16-1Thu
1 stopCathay Pacific
32h 25mORD-SIN
S$ 1,968

Search by stops

Search by airline

Search by price

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.
27-11Wed
2 stopsIndiGo
36h 45mSIN-ORD
S$ 770
23-12Mon
3 stops
36h 40mSIN-MDW
S$ 852
29-1Wed
1 stopTurkish Airlines
24h 45mSIN-ORD
S$ 883
27-12Fri
1 stopEVA Air
20h 20mSIN-ORD
S$ 927
21-12Sat
1 stopCathay Pacific
30h 45mSIN-ORD
S$ 968
26-12Thu
1 stopCathay Pacific
25h 35mSIN-ORD
S$ 974
17-1Fri
1 stopEVA Air
20h 20mSIN-ORD
S$ 1,005
16-1Thu
1 stopJapan Airlines
19h 15mSIN-ORD
S$ 1,386
16-1Thu
1 stopJapan Airlines
19h 15mSIN-ORD
S$ 1,388
17-1Fri
3 stopsUnited Airlines
33h 15mSIN-ORD
S$ 1,926

Search by stops

Search by airline

Search by price

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.
23-11Sat
multi-stopLufthansa
32h 40mSIN-ORD
3-12Tue
multi-stopLufthansa
33h 05mORD-SIN
S$ 1,607
23-11Sat
multi-stopLufthansa
26h 30mSIN-ORD
3-12Tue
multi-stopLufthansa
33h 05mORD-SIN
S$ 1,639
23-11Sat
multi-stopUnited Airlines
24h 13mSIN-ORD
3-12Tue
multi-stopUnited Airlines
25h 55mORD-SIN
S$ 1,653
22-11Fri
multi-stop
25h 35mSIN-ORD
3-12Tue
multi-stop
27h 55mORD-SIN
S$ 1,846
22-11Fri
multi-stop
25h 35mSIN-ORD
3-12Tue
multi-stop
49h 50mORD-SIN
S$ 1,898
22-11Fri
multi-stopDelta
36h 28mSIN-ORD
3-12Tue
multi-stopDelta
31h 55mORD-SIN
S$ 2,726
22-11Fri
multi-stopDelta
34h 16mSIN-MDW
3-12Tue
multi-stopDelta
38h 53mMDW-SIN
S$ 3,477
23-11Sat
multi-stopAir China
33h 00mSIN-ORD
3-12Tue
multi-stopAir China
47h 07mORD-SIN
S$ 4,266
23-11Sat
multi-stopDelta
24h 46mSIN-MDW
3-12Tue
multi-stopDelta
38h 53mMDW-SIN
S$ 6,373

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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