Find cheap flights to Chicago

Find cheap flights to Chicago

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Boston (BOS)
Chicago All airports
Fri 25-9
Fri 2-10
Any month
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Good to know

Low season

September Best time to beat the crowds (3% less expensive on average)

High season

January Most popular time to fly (8% more expensive on average)

Average price of a return ticket

S$ 1,083 (avg. price over the last 2 weeks)

Good deal for a return ticket

S$ 815 or less

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found return tickets to Chicago for the following prices or less: From Singapore Changi S$ 1,115
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, February and December. The cheapest month to fly to Chicago is September.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Chicago flights

What is the cheapest flight to Chicago?

Which Chicago airport is closest to central Chicago?

How does KAYAK find such low prices 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?

What is the Hacker Fare option on flights to Chicago?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

Top 5 airlines flying to Chicago

Scores according to KAYAK customer reviews

8.7
Japan Airlines
Overall score based on 4,475 reviews
8.9
Boarding
8.6
Comfort
9.0
Crew
8.5
Entertainment
8.4
Food
Airline reviews
Read more about Japan Airlines

Book Cheap Chicago Plane Tickets

Recent return flight deals

15-12
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2 stops
Multiple Airlines
25h 59m
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Tue
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Multiple Airlines
33h 05m
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Turkish Airlines
32h 20m
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Turkish Airlines
30h 20m
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Japan Airlines
23h 05m
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Japan Airlines
30h 05m
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EVA Air
42h 00m
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EVA Air
21h 50m
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SWISS
26h 25m
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SWISS
32h 40m
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Lufthansa
25h 00m
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Lufthansa
29h 45m
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Ethiopian Air
43h 30m
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Ethiopian Air
39h 20m
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Etihad Airways
27h 25m
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Etihad Airways
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Turkish Airlines
32h 20m
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Singapore Airlines
35h 55m
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Turkish Airlines
32h 20m
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Turkish Airlines
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Japan Airlines
19h 20m
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Japan Airlines
30h 05m
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Multiple Airlines
46h 42m
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Multiple Airlines
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KLM
34h 50m
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KLM
33h 45m
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Asiana Airlines
28h 35m
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Asiana Airlines
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Lufthansa
25h 00m
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Lufthansa
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Multiple Airlines
24h 35m
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Multiple Airlines
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Lufthansa
27h 05m
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17-1
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Lufthansa
30h 05m
ORD - SIN
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1 stop
Multiple Airlines
25h 30m
SIN - ORD
17-1
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Multiple Airlines
26h 15m
ORD - SIN
Show more results

Recent one-way flight deals

25-10
Sun
3 stops
Multiple Airlines
52h 00m
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Qatar Airways
31h 05m
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Delta
21h 00m
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Lufthansa
29h 30m
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3 stops
Multiple Airlines
52h 00m
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British Airways
25h 20m
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China Eastern
61h 00m
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Asiana Airlines
57h 09m
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Multiple Airlines
49h 30m
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Etihad Airways
33h 20m
SIN - ORD
27-10
Tue
3 stops
Multiple Airlines
57h 55m
SIN - MDW
29-10
Thu
2 stops
Delta
33h 25m
SIN - MDW
30-10
Fri
3 stops
Multiple Airlines
58h 55m
SIN - MDW
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2 stops
Multiple Airlines
26h 31m
SIN - ORD
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Thu
2 stops
Multiple Airlines
39h 24m
SIN - ORD
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1 stop
KLM
27h 05m
SIN - ORD
11-12
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2 stops
Japan Airlines
28h 37m
SIN - ORD
26-10
Mon
3 stops
Multiple Airlines
39h 27m
SIN - MDW
25-10
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2 stops
Multiple Airlines
33h 25m
SIN - MDW
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Sun
2 stops
Multiple Airlines
35h 05m
SIN - ORD
Show more results
*
Prices are per person, are for e–tickets and include all taxes & fees in SGD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller
At KAYAK we don’t set prices, so it’s not possible for us to guarantee what other companies are selling.

We aggregate tons of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we don't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car hires can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find on occasion that certain prices are no longer available.

More questions or if you have a bad price to report to us
Please send us an and someone from our team will get back to you promptly.

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