Rp 1,143,434+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 16/2. 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.
CHI — DPS
12 Mar — 19 Mar1
1 adult
1 adult, Economy, 0 bags

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 10 February 2026.

Cheapest airline

United Airlines

Good round-trip deal

Rp 2,982,848 or less

Good one-way deal

Rp 1,311,586 or less
On average, United Airlines currently has the cheapest one-way flight from Chicago (avg. price of Rp 27,479,570).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Find flights from Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 10 February 2026.

Fri 8/521.30
ORD
-
BOS
Nonstop2h 29m
United Airlines
Sun 10/506.00
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 9/2Rp 2,202,791
Tue 24/316.20
ORD
-
BOS
Nonstop2h 22m
United Airlines
Wed 25/312.07
BOS
-
ORD
1 stop5h 54m
United Airlines
Deal found 9/2Rp 2,236,422
Sat 4/421.30
ORD
-
BOS
Nonstop2h 29m
United Airlines
Sat 11/418.19
BOS
-
ORD
1 stop6h 18m
United Airlines
Deal found 8/2Rp 2,253,237
Fri 26/621.26
ORD
-
BOS
Nonstop2h 33m
United Airlines
Tue 30/620.05
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 8/2Rp 2,270,052
Tue 24/210.00
ORD
-
BOS
Nonstop2h 20m
JetBlue
Wed 11/307.00
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 9/2Rp 2,286,867
Thu 2/406.00
ORD
-
BOS
Nonstop2h 25m
United Airlines
Mon 6/407.00
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 7/2Rp 2,303,682
Mon 9/321.15
ORD
-
BOS
Nonstop2h 20m
United Airlines
Mon 16/307.16
BOS
-
ORD
Nonstop3h 06m
United Airlines
Deal found 9/2Rp 2,354,128
Thu 26/321.15
ORD
-
BOS
Nonstop2h 20m
United Airlines
Sun 29/309.20
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 8/2Rp 2,370,943
Thu 5/312.41
ORD
-
BOS
1 stop6h 17m
JetBlue
Wed 11/307.00
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 9/2Rp 2,387,758
Thu 5/312.41
ORD
-
BOS
1 stop6h 17m
JetBlue
Sun 8/307.00
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 9/2Rp 2,404,574
Wed 8/721.26
ORD
-
BOS
Nonstop2h 33m
United Airlines
Wed 22/706.00
BOS
-
ORD
Nonstop2h 58m
United Airlines
Deal found 10/2Rp 2,438,204
Thu 12/307.00
ORD
-
BOS
Nonstop2h 25m
Delta
Wed 18/307.15
BOS
-
ORD
Nonstop3h 10m
Delta
Deal found 8/2Rp 2,471,834

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 10 February 2026. In the last 7 days, Cheapflights users made a total of 22,532 searches

Fly to

Denpasar

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 16/5

21.30-00.59

Nonstop2h 29m

Boston Logan Intl

Tue 19/5

05.45-09.37

1 stop4h 52m

Rp 2,253,237

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/4

06.00-09.25

Nonstop2h 25m

Boston Logan Intl

Mon 6/4

07.00-09.00

Nonstop3h 00m

Rp 2,303,682

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 26/3

21.15-00.35

Nonstop2h 20m

Boston Logan Intl

Sun 29/3

09.20-11.20

Nonstop3h 00m

Rp 2,370,943

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 3/3

10.00-13.20

Nonstop2h 20m

Boston Logan Intl

Sat 7/3

17.10-23.00

1 stop6h 50m

Rp 2,387,758

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 19/5

19.15-22.49

Nonstop2h 34m

Boston Logan Intl

Tue 26/5

20.40-22.35

Nonstop2h 55m

Rp 2,387,758

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 7/3

12.59-20.23

1 stop6h 24m

Boston Logan Intl

Mon 9/3

07.00-09.10

Nonstop3h 10m

Rp 2,404,574

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 6/4

06.00-09.25

Nonstop2h 25m

Boston Logan Intl

Thu 9/4

06.00-10.44

1 stop5h 44m

Rp 2,471,834

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/5

19.15-22.49

Nonstop2h 34m

Boston Logan Intl

Sat 16/5

12.00-13.54

Nonstop2h 54m

Rp 2,555,910

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 25/3

13.09-18.41

1 stop4h 32m

Boston Logan Intl

Fri 27/3

07.16-09.22

Nonstop3h 06m

Rp 2,555,910

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 24/3

13.06-19.36

1 stop5h 30m

Boston Logan Intl

Sat 28/3

07.16-09.22

Nonstop3h 06m

Rp 2,555,910

Flights are sorted by cheapest return flights first.

Deals found on 8/2

Showing 1-10 of 60 results
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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago?

Use this chart to determine the optimal time to book a return flight from Chicago to Denpasar. Price data was last updated on 6 February 2026.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 37 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago?

Currently, January is the cheapest month in which you can book a flight from Chicago (average of Rp 11,434,337). Flying from Chicago in June will prove the most costly (average of Rp 20,531,360). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,152 flights per day), Detroit (840 flights per day) and Toronto (716 flights per day).

Los Angeles
Los Angeles
From Rp 2,992,601
Raleigh-Durham
Raleigh-Durham
From Rp 2,978,813
Mexico City Benito Juarez
Mexico City Benito Juarez
From Rp 6,593,576
New York
New York
From Rp 1,311,586

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is New York, with prices starting at Rp 1,311,586. Explore other affordable destinations below.

New York
New York
From Rp 1,311,586
Raleigh-Durham
Raleigh-Durham
From Rp 2,978,813
Los Angeles
Los Angeles
From Rp 2,992,601
Cleveland Hopkins Intl
Cleveland Hopkins Intl
From Rp 3,511,182

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Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 10 February 2026.

  • What are the most popular destinations to fly to from Chicago?

    The most popular destinations from Chicago this month are Atlanta, Ahmedabad, Boston. The top year-round destinations include Atlanta, Boston, Ahmedabad.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently January; with June being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago?

    View the cheapest flight destinations from Chicago:
    Fly from Chicago to Denpasar from Rp 12,947,705

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago, users can toggle the no change fees filter when performing a flight search.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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How does Cheapflights help users find flights from Chicago?

Cheapflights makes it easy to find flights from Chicago by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Yes! Start tracking prices for flights from Chicago today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive the alerts.

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