$588 Find Cheap Flights from Singapore 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 5/8. 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
1 adult, Economy, 0 bags

KAYAK searches 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Singapore to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Singapore 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Singapore to Chicago

Wed, Sep 16 - Tue, Sep 29
ANA Logo
12:50 am - 2:55 pm
SIN
-
ORD
27h 05m
1 stop
ANA Logo
5:45 pm - 6:40 am
ORD
-
SIN
23h 55m
1 stop
$798ANA
Wed, Sep 16 - Tue, Sep 29
ANA Logo
6:15 am - 2:55 pm
SIN
-
ORD
21h 40m
1 stop
ANA Logo
5:45 pm - 6:40 am
ORD
-
SIN
23h 55m
1 stop
$802ANA
Sat, Sep 19 - Mon, Oct 5
ANA Logo
12:50 am - 3:05 pm
SIN
-
ORD
27h 15m
1 stop
ANA Logo
12:00 pm - 6:40 am
ORD
-
SIN
29h 40m
1 stop
$851ANA
Sun, Sep 20 - Tue, Oct 6
ANA Logo
12:50 am - 3:05 pm
SIN
-
ORD
27h 15m
1 stop
ANA Logo
12:00 pm - 6:40 am
ORD
-
SIN
29h 40m
1 stop
$852ANA
Mon, Sep 14 - Tue, Sep 29
Korean Air Logo
10:00 pm - 9:30 am
SIN
-
ORD
24h 30m
1 stop
Korean Air Logo
12:10 pm - 5:00 am
ORD
-
SIN
27h 50m
1 stop
$958Korean Air
Wed, Apr 22 - Fri, Apr 24
Japan Airlines Logo
9:50 pm - 11:59 pm
SIN
-
ORD
39h 09m
2 stops
Japan Airlines Logo
10:15 am - 12:20 am
ORD
-
SIN
25h 05m
1 stop
$1,042Japan Airlines
Sun, Jun 7 - Sun, Aug 9
Delta Logo
10:00 pm - 4:16 pm
SIN
-
MDW
31h 16m
2 stops
Delta Logo
6:05 am - 5:00 am
MDW
-
SIN
33h 55m
2 stops
$1,217Delta
Sun, Jun 7 - Sun, Aug 9
Delta Logo
10:00 pm - 4:16 pm
SIN
-
MDW
31h 16m
2 stops
Delta Logo
6:05 am - 5:00 am
MDW
-
SIN
33h 55m
2 stops
$1,227Delta
Sun, Jun 7 - Sun, Aug 9
Multiple Airlines Logo
1:45 pm - 5:55 am
SIN
-
MDW
29h 10m
2 stops
Multiple Airlines Logo
8:35 pm - 12:35 pm
MDW
-
SIN
27h 00m
2 stops
$1,275Multiple Airlines
Sat, May 16 - Sat, Jun 13
Multiple Airlines Logo
1:45 pm - 5:40 am
SIN
-
MDW
28h 55m
2 stops
Multiple Airlines Logo
4:35 pm - 12:35 pm
MDW
-
SIN
31h 00m
2 stops
$1,454Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

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

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 February, where tickets cost $739 on average for return flights. On the other hand, the most expensive months are January and June, where the average cost of tickets from Singapore is $1,429 and $1,301 respectively. For one-way flights, the best month to travel is February with an average price of $739.

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 Greater Rockford Airport (RFD), with an average flight price of $160.

Find deals

Good to know

Low seasonFebruary
Cheapest flight$588
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly with an average 22% increase in price.
Flight from Singapore to Chicago

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 (9 miles). You'll travel 16 miles to reach the center of Chicago if you land in Chicago O'Hare Airport and 79 miles 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 travelers 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.

  • How many direct flights to Chicago are there each week?

    Each week there are around 13,191 direct flights from within Singapore to Chicago. The most common day for departures is Thursday, with 15% of flights taking off on this day.

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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.
First Class flights to Chicago
Business Class flights to Chicago
Premium Economy Class flights to Chicago
Economy Class flights to Chicago