SIN - CHI

S$ 626 Find Cheap Flights from Singapore to Chicago – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest return flight
S$ 1,011
Typical prices: S$ 1,377-S$ 2,188
Air Canada
Mon 12-11Sun 25-11
SIN - ORD • 1 stop
Cheapest one-way flight
S$ 626
Typical prices: S$ 757-S$ 1,135
Etihad Airways
Fri 9-11
SIN - ORD • 1 stop
Direct flights
Not available
There are currently no direct flights between Singapore and Chicago. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
23 weeks
in advance
Our data shows that travellers who book at least 23 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
When to travel
February
Cheapest • 26% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top stopover airports
Vancouver Intl (YVR)
Cheapest • Avg S$ 1,141 (return)
Taipei City Taiwan Taoyuan Intl (TPE)
Shortest trip • 21h 46m (one-way)
Insights
Insights
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you enjoy your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Singapore to Chicago (SIN-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Singapore to Chicago

Thu, 12 Nov - Wed, 25 Nov
Air Canada Logo
08:40 - 14:37SIN  Singapore Changi-ORD Chicago O'Hare Intl
19h 57m1 stop Vancouver Intl
Air Canada Logo
15:30 - 07:00ORD  Chicago O'Hare Intl-SIN Singapore Changi
25h 30m1 stop Vancouver Intl
S$ 1,011Air Canada
3+ days ago
Thu, 12 Nov - Wed, 25 Nov
Air Canada Logo
08:40 - 14:37SIN  Singapore Changi-ORD Chicago O'Hare Intl
19h 57m1 stop Vancouver Intl
Air Canada Logo
07:05 - 00:45ORD  Chicago O'Hare Intl-SIN Singapore Changi
27h 40m2 stops Montreal Pierre Elliott Trudeau Intl Tokyo Narita
S$ 1,025Air Canada
3+ days ago
Tue, 23 Feb - Fri, 26 Feb
Korean Air Logo
10:30 - 08:30SIN  Singapore Changi-ORD Chicago O'Hare Intl
36h 00m1 stop Incheon Intl
Korean Air Logo
11:10 - 20:25ORD  Chicago O'Hare Intl-SIN Singapore Changi
43h 15m1 stop Incheon Intl
S$ 1,051Korean Air
8 hours ago
Thu, 19 Nov - Mon, 23 Nov
Air Canada Logo
08:40 - 14:37SIN  Singapore Changi-ORD Chicago O'Hare Intl
19h 57m1 stop Vancouver Intl
Air Canada Logo
16:45 - 07:00ORD  Chicago O'Hare Intl-SIN Singapore Changi
48h 15m2 stops Toronto Pearson Intl Vancouver Intl
S$ 1,059Air Canada
3+ days ago
Sun, 8 Nov - Wed, 11 Nov
United Airlines Logo
22:20 - 05:47SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 27m1 stop San Francisco
United Airlines Logo
06:00 - 20:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
24h 15m1 stop San Francisco
S$ 1,463United Airlines
3+ days ago
Sun, 8 Nov - Wed, 11 Nov
United Airlines Logo
22:20 - 05:47SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 27m1 stop San Francisco
United Airlines Logo
06:00 - 20:15ORD  Chicago O'Hare Intl-SIN Singapore Changi
24h 15m1 stop San Francisco
S$ 1,474United Airlines
3+ days ago
Mon, 21 Dec - Thu, 7 Jan
United Airlines Logo
22:20 - 05:56SIN  Singapore Changi-ORD Chicago O'Hare Intl
21h 36m1 stop San Francisco
United Airlines Logo
08:45 - 06:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
32h 10m2 stops Los Angeles Tokyo Haneda
S$ 1,575United Airlines
2 days ago
Mon, 15 Mar - Fri, 14 May
EVA Air Logo
15:45 - 20:35SIN  Singapore Changi-ORD Chicago O'Hare Intl
41h 50m1 stop Taipei City Taiwan Taoyuan Intl
EVA Air Logo
00:30 - 11:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 25m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,725EVA Air
3+ days ago
Sat, 13 Mar - Fri, 14 May
EVA Air Logo
13:15 - 19:35SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 20m1 stop Taipei City Taiwan Taoyuan Intl
EVA Air Logo
00:30 - 11:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 25m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,725EVA Air
3+ days ago
Sun, 14 Mar - Fri, 14 May
EVA Air Logo
13:15 - 19:35SIN  Singapore Changi-ORD Chicago O'Hare Intl
20h 20m1 stop Taipei City Taiwan Taoyuan Intl
EVA Air Logo
00:30 - 11:55ORD  Chicago O'Hare Intl-SIN Singapore Changi
22h 25m1 stop Taipei City Taiwan Taoyuan Intl
S$ 1,725EVA Air
3+ days ago
Booking Insights

Price, demand, and travel trends for Singapore to Chicago flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

How much is a return flight from Singapore to Chicago?

Return flights from Singapore to Chicago typically range from S$ 1,377 to S$ 2,188. The lowest price found in the past 5 days was S$ 1,011 on Air Canada.

What is the cheapest Singapore to Chicago flight route?

There's little price difference between Singapore to Chicago routes. They average around S$ 1,635 return, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Singapore to Chicago?

Based on deals KAYAK users found in the last 12 months, Thursday is the cheapest day of the week to fly from Singapore to Chicago. It's 14% cheaper than the average day, while Wednesday is the most expensive, with prices 59% higher.

What is the cheapest month to fly from Singapore to Chicago?

•February is the cheapest month to fly from Singapore to Chicago at S$ 1,205 return.
•August (S$ 2,629) and July (S$ 1,709) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 118% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Singapore to Chicago the cheapest?

Flights from Singapore to Chicago are cheapest 23 weeks before departure. Booking in this window typically costs about 45% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Singapore to Chicago flights

Low season

October

Cheapest flight

S$ 626
Beat the crowds with an average 60% drop in travellers.
The most popular month to fly with an average 109% increase in travellers.
One-way flight from Singapore to Chicago O'Hare Intl Airport

When to book flights from Singapore to Chicago

Are your dates flexible? Find out the best times to travel from Singapore to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

Your Singapore to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • Which cabin classes can I book on flights from Singapore to Chicago?

    Two cabin classes are available on flights from Singapore to Chicago:

    • Economy class
    • Business Class

  • How long is a flight from Singapore to Chicago?

    A direct flight from Singapore to Chicago takes 00m, covering 24,232 km.

  • Do I need a passport to fly from Singapore to Chicago?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Singapore to Chicago flight?

    Return flights from Singapore to Chicago range from S$ 1,377 to S$ 2,188, with an average of S$ 1,635 over the past 12 months. Anything below S$ 1,377 counts as a good deal.

  • How expensive are last-minute Singapore to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 18% above the S$ 1,635 route average. Book 23 weeks before departure for the lowest fares.

  • How are flight prices from Singapore to Chicago looking right now?

    One-way fares from Singapore to Chicago are currently lower than usual. Average one-way flight prices are about S$ 689, which is 22% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) – daily rates from around S$ 22:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) – daily rates from around S$ 41:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) – daily rates from around S$ 36:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Singapore to Chicago?

    Flights from Singapore to Chicago usually depart from Singapore Changi (SIN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Singapore to Chicago pass through?

    One-stop flights from Singapore to Chicago most commonly connect through:

    • Tokyo Haneda (HND) – 28% of one-stop connections
    • Taipei City Taiwan Taoyuan Intl (TPE) – 22% of one-stop connections
    • San Francisco (SFO) – 19% of one-stop connections
    • Hong Kong Intl (HKG) – 10% of one-stop connections

  • Can I save money by using flexible dates for flights from Singapore to Chicago?

    Yes. Flexible dates can save you up to 46% on flights from Singapore to Chicago. Thursday is the cheapest departure day at S$ 1,409 return on average, while Wednesday is the most expensive at S$ 2,602, a difference of S$ 1,193.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different stopover airport from Singapore to Chicago?

    Flying via Taipei City Taiwan Taoyuan Intl (TPE) gives the shortest average 1-stop total travel time of 21h 46m, compared to 22h 42m via Incheon Intl (ICN) and 23h 02m via San Francisco (SFO).

  • What is the time difference between Singapore and Chicago?

    Chicago is 13 hours behind Singapore (Central Time vs Singapore Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Grant Park is one of the most viewed places in Chicago on KAYAK.

Your guide to booking Singapore to Chicago flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Wednesday. On this route, Thursday flights average S$ 1,409, which is about S$ 1,193 less than Wednesday fares (46% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 23 weeks before you fly. On this route, that window historically saves about 45% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Singapore to Chicago trip for February. Fares historically average S$ 1,205 return in that month – typically S$ 1,424 less than the most expensive month, which is August (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • Skylark Motel

More options for your flight from Singapore to Chicago

Complete your trip to Chicago with a hotel stay or car hire

Car rentals in Chicago
Hotels in Chicago