Rp 1,531,339+ 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 18/11. 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
28 Jul — 4 Aug1
1 adult
1 adult, Economy, 0 bags

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 28 June 2026. In the last 7 days, Cheapflights users made a total of 22,532 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 11/8

09.35-17.17

1 stop6h 42m

Boston Logan Intl

Sat 15/8

16.43-21.58

1 stop6h 15m

Rp 3,294,160

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Tue 21/7

07.00-11.14

Nonstop3h 14m

Fort Lauderdale

Fri 31/7

21.05-23.44

Nonstop3h 39m

Rp 3,365,384

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 17/7

19.25-23.00

Nonstop2h 35m

Boston Logan Intl

Sun 26/7

07.30-09.26

Nonstop2h 56m

Rp 3,400,997
Fastest return journey

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 7/8

19.30-23.00

Nonstop2h 30m

Boston Logan Intl

Sun 9/8

07.30-09.26

Nonstop2h 56m

Rp 3,400,997

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 27/7

19.25-23.00

Nonstop2h 35m

Boston Logan Intl

Sat 1/8

19.59-21.59

Nonstop3h 00m

Rp 3,400,997

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Fri 18/9

06.30-15.33

1 stop8h 03m

Fort Lauderdale

Sat 10/10

18.00-20.36

Nonstop3h 36m

Rp 3,543,447

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 30/7

15.19-18.59

Nonstop2h 40m

Boston Logan Intl

Fri 31/7

20.45-22.39

Nonstop2h 54m

Rp 3,579,060

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/8

19.30-23.00

Nonstop2h 30m

Boston Logan Intl

Thu 6/8

07.30-09.26

Nonstop2h 56m

Rp 3,614,672

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 14/7

06.00-11.16

1 stop4h 16m

Boston Logan Intl

Sun 19/7

06.00-07.58

Nonstop2h 58m

Rp 3,685,898

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/9

12.52-16.27

Nonstop2h 35m

Boston Logan Intl

Sun 13/9

06.00-07.59

Nonstop2h 59m

Rp 3,685,898

Flights are sorted by cheapest return flights first.

Deals found on 23/6

Showing 1-10 of 60 resultsSorted by cheapest first
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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.

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

Currently, November is the cheapest month in which you can book a flight from Chicago (average of Rp 10,541,311). Flying from Chicago in December will prove the most costly (average of Rp 16,310,541). 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: Detroit (1,230 flights per day), New York (1,190 flights per day) and Los Angeles (827 flights per day).

Seattle/Tacoma Intl
Seattle/Tacoma Intl
From Rp 29,900,998
Raleigh-Durham
Raleigh-Durham
From Rp 3,154,380
Mexico City Benito Juarez
Mexico City Benito Juarez
From Rp 6,982,194
New York
New York
From Rp 1,388,889

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 1,388,889. Explore other affordable destinations below.

New York
New York
From Rp 1,388,889
Raleigh-Durham
Raleigh-Durham
From Rp 3,154,380
Cleveland Hopkins Intl
Cleveland Hopkins Intl
From Rp 3,718,127
Mexico City Benito Juarez
Mexico City Benito Juarez
From Rp 6,982,194

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

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 78 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.

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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 28 June 2026.

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

    The most popular destinations from Chicago this month are Boston, Amman Queen Alia Intl Airport, Atlanta. 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 November; with December 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 16,648,860

  • 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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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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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