Rp 746,142+ 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 12/4. 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
27 Apr — 4 May1
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 March 2026. In the last 7 days, Cheapflights users made a total of 22,532 searches

Fly to

Route

Depart

Return

Price

Cheapest return flight

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 25/4

19.15-23.24

Nonstop3h 09m

Fort Lauderdale

Sat 2/5

22.04-00.24

Nonstop3h 20m

Rp 1,661,862

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sat 2/5

19.15-23.24

Nonstop3h 09m

Fort Lauderdale

Mon 4/5

20.55-23.15

Nonstop3h 20m

Rp 1,661,862

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Tue 28/4

05.05-09.10

Nonstop3h 05m

Fort Lauderdale

Sun 3/5

06.15-10.23

1 stop5h 08m

Rp 1,780,566

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sun 26/4

19.15-23.24

Nonstop3h 09m

Fort Lauderdale

Wed 29/4

06.15-10.23

1 stop5h 08m

Rp 1,899,271

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sun 19/4

19.15-23.24

Nonstop3h 09m

Fort Lauderdale

Fri 24/4

19.30-23.07

1 stop4h 37m

Rp 2,408,004

ChicagoFort Lauderdale

ORD - FLL

ORDFLL

Chicago O'Hare Intl

Sun 26/4

10.31-20.44

1 stop9h 13m

Fort Lauderdale

Sun 3/5

07.05-09.36

Nonstop3h 31m

Rp 2,408,004

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/5

07.00-10.35

Nonstop2h 35m

Boston Logan Intl

Tue 12/5

16.30-22.27

1 stop6h 57m

Rp 2,475,835

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 31/5

07.00-10.35

Nonstop2h 35m

Boston Logan Intl

Wed 3/6

05.40-10.29

1 stop5h 49m

Rp 2,662,371

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/4

14.10-17.38

Nonstop2h 28m

Boston Logan Intl

Mon 13/4

16.55-18.59

Nonstop3h 04m

Rp 2,662,371
Fastest return journey

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/6

21.26-00.59

Nonstop2h 33m

Boston Logan Intl

Sun 7/6

06.00-07.58

Nonstop2h 58m

Rp 2,831,948

Flights are sorted by cheapest return flights first.

Deals found on 24/3

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.

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 13 March 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 11,700,865). Flying from Chicago in June will prove the most costly (average of Rp 19,942,344). 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 (1,037 flights per day), Detroit (762 flights per day) and Orlando (679 flights per day).

Seattle/Tacoma Intl
Seattle/Tacoma Intl
From Rp 28,476,174
Raleigh-Durham
Raleigh-Durham
From Rp 3,004,070
Mexico City Benito Juarez
Mexico City Benito Juarez
From Rp 6,649,483
New York
New York
From Rp 1,322,706

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 1,322,706. Explore other affordable destinations below.

New York
New York
From Rp 1,322,706
Raleigh-Durham
Raleigh-Durham
From Rp 3,004,070
Cleveland Hopkins Intl
Cleveland Hopkins Intl
From Rp 3,540,953
Mexico City Benito Juarez
Mexico City Benito Juarez
From Rp 6,649,483

Browse thousands of different options on Cheapflights for your next trip

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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 March 2026.

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

    The most popular destinations from Chicago this month are Atlanta, Boston, Austin. The top year-round destinations include Boston, Atlanta, 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 11,989,147
    Fly from Chicago to Jakarta from Rp 15,143,293

  • 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

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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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