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Our biggest upcoming deals to Chicago

These are the best offers on flights to Chicago you’ll find over the next 60 days, with savings of up to S$ 1,618. Don’t miss out!

71%
SingaporeChicago
Saudia
One way
Economy
Sat, Sep 7
S$ 652
S$ 2,270
69%
SingaporeChicago
Saudia
One way
Economy
Sat, Sep 14
S$ 693
S$ 2,270
68%
SingaporeChicago
STARLUX Airlines
One way
Economy
Fri, Sep 13
S$ 721
S$ 2,270
68%
SingaporeChicago
ZIPAIR
One way
Economy
Tue, Sep 3
S$ 725
S$ 2,270
67%
SingaporeChicago
Saudia
One way
Economy
Wed, Sep 11
S$ 739
S$ 2,270
67%
SingaporeChicago
STARLUX Airlines
One way
Economy
Thu, Sep 12
S$ 756
S$ 2,270

City breaks to Chicago for less

Whether it's a quick getaway or a business trip to remember, our 3–7 day round trips are perfect for experiencing Chicago affordably.

7 Day Trip
Wed, Sep 11 - Tue, Sep 17
7 Day Trip
Singapore
Chicago
S$ 1181
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5 Day Trip
Tue, Sep 17 - Sat, Sep 21
5 Day Trip
Singapore
Chicago
S$ 1244
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6 Day Trip
Thu, Aug 15 - Tue, Aug 20
6 Day Trip
Singapore
Chicago
S$ 1258
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6 Day Trip
Fri, Sep 13 - Wed, Sep 18
6 Day Trip
Singapore
Chicago
S$ 1297
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7 Day Trip
Sat, Sep 14 - Fri, Sep 20
7 Day Trip
Singapore
Chicago
S$ 1362
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6 Day Trip
Sun, Sep 15 - Fri, Sep 20
6 Day Trip
Singapore
Chicago
S$ 1365
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Major Chicago Airports

Learn about the different airports in Chicago, find the best flight and transfer options, and plan your journey.

Popular Airlines Flying to Chicago

See which airlines fly to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.

Saudia
From S$ 651
STARLUX Airlines
From S$ 720
ZIPAIR
From S$ 725
China Airlines
From S$ 778
United Airlines
From S$ 816

Find more flights and airlines

Find cheapest flight ticket to Chicago from Singapore

Cheapest direct flight price

S$ 817

Off-season for travel

April

Peak season for travel

July

Flight distance

15,077.88km

Popular airline

Air Canada

Cheapest month

September

Frequently Asked Questions

  • How much is a flight from Singapore to Chicago?

    The average ticket price to Chicago is S$ 1,009. Please use this price as a reference only.
  • How long is the flight to Chicago?

    • Approx. 23 hours 39 minutes to fly from Singapore to Chicago.
    • Approx. 4 hours 8 minutes to fly from Los Angeles to Chicago.
    • Approx. 2 hours 38 minutes to fly from New York to Chicago.
    • Approx. 11 hours 50 minutes to fly from Tokyo to Chicago.
  • How to get cheap flights to Chicago?

    You can book cheaper flights in the following ways:
    • Search for tickets to a city or airport near Chicago.
    • Look up different airlines that have flights to Chicago.
    • Browse different departure dates from the same month.
    • Filter for different departure times from the same day.
    • Check for discount information on various social media sites.
    • Explore deals and discounts on airline websites.
  • What is the most popular month to visit Chicago?

    Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is July. The average price of flight tickets to Chicago in July is S$ 1,121.
  • When to buy flight tickets to Chicago the cheapest?

    Flight tickets to Chicago are the cheapest in September compared to other months, the average price is S$ 332.
  • What are the major airports in Chicago?

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • Which popular airlines have flights to Chicago?

    Popular airlines with flights to Chicago: Frontier Airlines , Spirit Airlines , and American Airlines .