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Flights to Chicago

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.
United Airlines logo United Airlines
American Airlines logo American Airlines
Air Canada logo Air Canada
Eva Air logo Eva Air
Delta Air Lines logo Delta Air Lines
Japan Airlines logo Japan Airlines
Cathay Pacific logo Cathay Pacific
All Nippon Airways logo All Nippon Airways
Thai Airways logo Thai Airways
Korean Air logo Korean Air
Philippine Airlines logo Philippine Airlines
Air New Zealand logo Air New Zealand
Qatar Airways logo Qatar Airways
Volaris logo Volaris
Frontier Airlines logo Frontier Airlines
British Airways logo British Airways
Etihad Airways logo Etihad Airways
Emirates logo Emirates
Turkish Airlines logo Turkish Airlines

Latest Flight 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 TWD 707. Don’t miss out!

54%
Singapore Chicago
Air Canada Air Canada
One way
Economy
Tue, Nov 3
TWD 598
TWD 1,305
18%
New York Chicago
Delta Air Lines Delta Air Lines
One way
Economy
Sat, Oct 24
TWD 227
TWD 278
42%
Los Angeles Chicago
Frontier Airlines Frontier Airlines
One way
Economy
Sat, Oct 24
TWD 160
TWD 277
43%
San Francisco Chicago
Frontier Airlines Frontier Airlines
One way
Economy
Wed, Nov 4
TWD 187
TWD 328
57%
Bangkok Chicago
Etihad Airways Etihad Airways
One way
Economy
Tue, Nov 17
TWD 519
TWD 1,198
36%
Toronto Chicago
Air Canada Air Canada
One way
Economy
Tue, Nov 10
TWD 235
TWD 370
48%
Atlanta Chicago
Frontier Airlines Frontier Airlines
One way
Economy
Tue, Oct 13
TWD 126
TWD 244
-15%
Manila Chicago
Philippine Airlines Philippine Airlines
One way
Economy
Sun, Oct 18
TWD 1,144
TWD 992
48%
Boston Chicago
Delta Air Lines Delta Air Lines
One way
Economy
Sat, Oct 10
TWD 160
TWD 309

When is the cheapest time to book flights to Chicago?

Depart from:

What is the cheapest month for one-way flights from Singapore to Chicago?

The average price of one-way flights from Singapore to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from Singapore to Chicago is September, with an average price of TWD 865, and the most expensive month is March, with an average price of up to TWD 1,446.

TWD 1,446
TWD 1,156
TWD 865
TWD 575
    Cheapest
  • S$ 985
    Oct
  • S$ 1,037
    Nov
  • S$ 920
    Dec
  • S$ 1,278
    Jan
  • S$ 866
    Feb
  • S$ 1,446
    Mar
  • S$ 1,324
    Apr
  • S$ 1,107
    May
  • S$ 1,079
    Jun
  • S$ 1,144
    Jul
  • S$ 1,349
    Aug
  • S$ 865
    Sep

What is the cheapest month for round-trip flights from Singapore to Chicago?

The average price of round-trip flights from Singapore to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for round-trip flights from Singapore to Chicago is April, with an average price of TWD 1,274, and the most expensive month is December, with an average price of up to TWD 2,361.

TWD 2,361
TWD 1,818
TWD 1,274
TWD 731
    Cheapest
  • S$ 1,537
    Oct
  • S$ 1,852
    Nov
  • S$ 2,361
    Dec
  • S$ 1,987
    Jan
  • S$ 1,843
    Feb
  • S$ 2,037
    Mar
  • S$ 1,274
    Apr
  • S$ 1,994
    May
  • S$ 2,252
    Jun
  • S$ 1,958
    Jul
  • S$ 2,241
    Aug
  • S$ 1,570
    Sep

Which day of the week has the lowest fares for flights from Singapore to Chicago?

The average weekly fares for flights from Singapore to Chicago on different dates. (Based on Trip.com’s data from the past 12 months)

Based on Trip.com’s data from the past 12 months, Thursday offers the lowest fares for flights from Singapore to Chicago, while Sunday typically has the highest fares.

TWD 1,236
TWD 1,088
TWD 939
TWD 791
    Cheapest
  • S$ 1,138
    Mon
  • S$ 1,231
    Tue
  • S$ 1,173
    Wed
  • S$ 939
    Thu
  • S$ 1,073
    Fri
  • S$ 1,211
    Sat
  • S$ 1,236
    Sun

Round-trip fights to Chicago

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

8 day trip
Thu, Oct 8- Thu, Oct 15
8 day trip
Singapore
Chicago
TWD 886
Search
3 day trip
Mon, Nov 9- Wed, Nov 11
3 day trip
Seoul
Chicago
TWD 918
Search
8 day trip
Wed, Oct 21- Wed, Oct 28
8 day trip
Taipei
Chicago
TWD 926
Search
8 day trip
Tue, Oct 13- Tue, Oct 20
8 day trip
Manila
Chicago
TWD 989
Search
8 day trip
Tue, Oct 13- Tue, Oct 20
8 day trip
Bangkok
Chicago
TWD 1,072
Search
8 day trip
Sun, Nov 8- Sun, Nov 15
8 day trip
Ho Chi Minh City
Chicago
TWD 1,084
Search
View more return flights

Find cheapest flight ticket to Chicago from

Cheapest one-way flight priceS$ 596
Cheapest monthDecember
Peak season for travelJanuary
Flight distance15,077.88km
Popular airlineAir Canada

FAQs about Flights to Chicago

  • How much is a flight from Singapore to Chicago?

    The average ticket price to Chicago is S$ 550. Please use this price as a reference only.
    • Approx. 21 hours 51 minutes to fly from Singapore to Chicago.
    • Approx. 2 hours 43 minutes to fly from New York to Chicago.
    • Approx. 4 hours 10 minutes to fly from Los Angeles to Chicago.
    • Approx. 1 hour 41 minutes to fly from Minneapolis 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.
  • Understanding peak and off travel seasons to Chicago can help you arrange your travel plans accordingly. The most popular month to visit Chicago is November. The average price of flight tickets to Chicago in November is S$ 366.
  • Flight tickets to Chicago are the cheapest in December compared to other months, the average price is S$ 335.
  • Popular airlines with flights to Chicago: American Airlines , United Airlines , and Frontier Airlines .

Find Cheap Flights & Deals with Trip.com

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Note: Prices shown on this page are the lowest estimated prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.