Find cheap flights to Chicago

Find cheap flights to Chicago

Return
Economy
Boston (BOS)
Chicago All airports
Wed 8-7
Wed 15-7
Any month
Compare vs KAYAK |
Search hundreds of travel sites at once for deals on flights to Chicago

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$ 1,195 (avg. price over the last 2 weeks)

Good deal for a return ticket

S$ 931 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$ 1,295
  • 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’s flight Price Forecast tool help me choose the right time to buy?

Top 5 airlines flying to Chicago

Scores according to KAYAK customer reviews

8.7
Japan Airlines
Overall score based on 4,472 reviews
8.9
Boarding
8.6
Comfort
9.1
Crew
8.6
Entertainment
8.5
Food
Airline reviews
Read more about Japan Airlines

Book Cheap Chicago Plane Tickets (Return)

Airports
Origin
Singapore
S$ 1,164
only
S$ 1,164
Destination
Chicago
S$ 1,164
only
S$ 1,164
Mon, 19 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
31h 10m
Tue, 27 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
30h 20m
S$ 1,164
Trip: 9 days
Based on null reviews
Mon, 19 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
29h 25m
Wed, 28 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
29h 10m
S$ 1,233
Trip: 10 days
Based on null reviews
Fri, 21 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
31h 17m
Sat, 24 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
29h 20m
S$ 1,256
Trip: 65 days
Based on null reviews
Thu, 22 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
24h 30m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
24h 45m
S$ 1,311
Trip: 10 days
Based on null reviews
Thu, 22 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
25h 20m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
25h 45m
S$ 1,356
Trip: 10 days
Based on null reviews
Mon, 19 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
21h 05m
Tue, 27 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
24h 00m
S$ 1,448
Trip: 9 days
Based on null reviews
Fri, 23 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 20m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
26h 30m
S$ 1,516
Trip: 9 days
Based on null reviews
Sat, 22 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
30h 40m
Sat, 24 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
29h 20m
S$ 1,561
Trip: 64 days
Based on null reviews
Sat, 22 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
29h 00m
Sat, 24 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
37h 15m
S$ 1,567
Trip: 64 days
Based on null reviews
Sat, 22 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
28h 35m
Sat, 24 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
29h 40m
S$ 1,593
Trip: 64 days
Based on null reviews
Sat, 22 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
31h 10m
Sat, 24 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
30h 20m
S$ 1,169
Trip: 64 days
Based on null reviews
Mon, 19 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
29h 25m
Sun, 25 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
27h 15m
S$ 1,251
Trip: 7 days
Based on null reviews
Fri, 23 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
24h 40m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
31h 20m
S$ 1,265
Trip: 9 days
Based on null reviews
Fri, 23 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
29h 20m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
30h 25m
S$ 1,313
Trip: 9 days
Based on null reviews
Thu, 22 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
25h 20m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
35h 45m
S$ 1,375
Trip: 10 days
Based on null reviews
Fri, 23 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 30m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
30h 20m
S$ 1,254
Trip: 9 days
Based on null reviews
Thu, 22 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
20h 40m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
30h 15m
S$ 1,271
Trip: 10 days
Based on null reviews
Sat, 17 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
29h 25m
Thu, 29 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
27h 15m
S$ 1,277
Trip: 13 days
Based on null reviews
Fri, 23 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 20m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
23h 10m
S$ 1,520
Trip: 9 days
Based on null reviews
Fri, 23 Oct
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
26h 15m
Sat, 31 Oct
ORD
Chicago O'Hare Airport
SIN
Singapore Changi Airport
32h 40m
S$ 1,569
Trip: 9 days
Based on null reviews
Show more results

Book Cheap Chicago Plane Tickets (One-way)

Airports
Origin
Singapore
S$ 760
only
S$ 760
Destination
Chicago
S$ 760
only
S$ 760
Mon, 14 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
57h 34m
S$ 760
Based on null reviews
Sun, 13 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 10m
S$ 951
Based on null reviews
Sun, 13 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 10m
S$ 993
Based on null reviews
Sun, 13 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
24h 30m
S$ 1,086
Based on null reviews
Tue, 8 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
20h 40m
S$ 1,103
Based on null reviews
Wed, 9 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
42h 55m
S$ 1,119
Based on null reviews
Wed, 9 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
57h 34m
S$ 775
Based on null reviews
Tue, 15 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
57h 34m
S$ 777
Based on null reviews
Wed, 9 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 10m
S$ 952
Based on null reviews
Thu, 10 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
57h 34m
S$ 793
Based on null reviews
Thu, 13 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 10m
S$ 969
Based on null reviews
Sun, 13 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
55h 04m
S$ 807
Based on null reviews
Tue, 8 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
24h 30m
S$ 1,089
Based on null reviews
Sat, 15 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
20h 55m
S$ 1,114
Based on null reviews
Sat, 12 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
57h 34m
S$ 810
Based on null reviews
Fri, 11 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 20m
S$ 986
Based on null reviews
Mon, 14 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
40h 00m
S$ 1,090
Based on null reviews
Sat, 12 Sep
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
24h 53m
S$ 819
Based on null reviews
Mon, 6 Jul
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
23h 45m
S$ 1,097
Based on null reviews
Fri, 14 Aug
SIN
Singapore Changi Airport
ORD
Chicago O'Hare Airport
33h 20m
S$ 1,004
Based on null reviews
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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