Find flights
Airlines

AED 367+ Cheap flights from Chicago

This is the cheapest return flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/1. 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 — DXB
29 Dec — 5 Jan1
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 29 November 2025.

Good round-trip deal

AED 652 or less

Good one-way deal

AED 532 or less
Price to beat on a round-trip flight from Chicago.
Search Deals
Price to beat on a one-way flight from Chicago.
Search Deals

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 29 November 2025.

Sun 8/208:45ORD - PUJ
1 stop8h 15mJetBlue
Fri 13/214:07PUJ - ORD
1 stop11h 03mJetBlue
Deal found 27/11AED 948
Sun 1/306:04ORD - PUJ
1 stop11h 24mJetBlue
Thu 5/312:37PUJ - ORD
1 stop12h 17mJetBlue
Deal found 29/11AED 970
Thu 5/209:40ORD - PUJ
1 stop7h 27mJetBlue
Sun 15/212:27PUJ - ORD
1 stop12h 43mJetBlue
Deal found 27/11AED 992
Sun 1/306:04ORD - PUJ
1 stop11h 24mJetBlue
Sat 7/312:37PUJ - ORD
1 stop12h 19mJetBlue
Deal found 29/11AED 999
Thu 7/520:21ORD - PUJ
1 stop13h 12mJetBlue
Mon 11/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 29/11AED 1,021
Wed 1/408:00ORD - PUJ
1 stop8h 45mJetBlue
Sun 5/412:54PUJ - ORD
1 stop11h 05mJetBlue
Deal found 29/11AED 1,032
Sun 5/408:00ORD - PUJ
1 stop8h 45mJetBlue
Mon 13/415:05PUJ - ORD
1 stop8h 54mJetBlue
Deal found 29/11AED 1,050
Mon 4/520:21ORD - PUJ
1 stop13h 12mJetBlue
Tue 12/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 28/11AED 1,054
Sat 28/206:04ORD - PUJ
1 stop11h 24mJetBlue
Sun 1/312:37PUJ - ORD
1 stop12h 17mJetBlue
Deal found 28/11AED 1,069
Fri 1/520:21ORD - PUJ
1 stop12h 49mJetBlue
Tue 5/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 29/11AED 1,083
Sun 17/520:21ORD - PUJ
1 stop13h 12mJetBlue
Tue 19/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 29/11AED 1,091
Fri 20/312:50ORD - DXB
1 stop27h 20mTurkish Airlines
Fri 3/413:50DXB - ORD
1 stop28h 50mTurkish Airlines
Deal found 28/11AED 2,453

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 29 November 2025. In the last 7 days, Cheapflights users made a total of 220,657 searches

Fly to

Dubai

Route

Departure

Return

Price

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 1/3

06:04-19:28

1 stop11h 24m

Punta Cana

Mon 9/3

11:37-22:56

1 stop12h 19m

AED 948

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 1/3

06:04-19:28

1 stop11h 24m

Punta Cana

Fri 6/3

12:37-22:56

1 stop12h 19m

AED 948

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 15/5

20:21-10:10

1 stop12h 49m

Punta Cana

Wed 20/5

18:42-08:45

1 stop15h 03m

AED 999

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 15/5

20:21-10:10

1 stop12h 49m

Punta Cana

Mon 18/5

18:42-08:45

1 stop15h 03m

AED 999

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 1/3

06:04-19:28

1 stop11h 24m

Punta Cana

Sat 7/3

12:37-22:56

1 stop12h 19m

AED 999

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 14/5

20:21-10:33

1 stop13h 12m

Punta Cana

Wed 20/5

18:42-08:45

1 stop15h 03m

AED 999

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 14/5

20:21-10:33

1 stop13h 12m

Punta Cana

Mon 18/5

18:42-08:45

1 stop15h 03m

AED 999

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 15/5

20:21-10:10

1 stop12h 49m

Punta Cana

Tue 19/5

18:42-08:45

1 stop15h 03m

AED 1,021

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 14/5

20:21-10:33

1 stop13h 12m

Punta Cana

Tue 19/5

18:42-08:45

1 stop15h 03m

AED 1,021

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 14/5

20:21-10:33

1 stop13h 12m

Punta Cana

Sat 23/5

18:42-07:55

1 stop14h 13m

AED 1,083

Flights are sorted by cheapest return flights first.

Deals found on 29/11

Showing 1-10 of 60 results
1
2
3
...
6

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 Dubai. Price data was last updated on 28 November 2025.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 65 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, November is the cheapest month in which you can book a flight from Chicago (average of AED 2,071). Flying from Chicago in June will prove the most costly (average of AED 3,239). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: Emirates. This airline departs to the following popular destinations: Dubai.

Etihad Airways
Etihad Airways
From AED 3,012
Air Canada
Air Canada
From AED 557
Emirates
Emirates
From AED 3,286

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: Toronto (746 flights per day), Detroit (614 flights per day), and New York (606 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545
Dubai Intl
Dubai Intl
From AED 2,295
Zurich
Zurich
From AED 3,396
Reykjavik
Reykjavik
From AED 1,570

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Cincinnati Cinci./N. Kentucky, with prices starting at AED 532. Explore other affordable destinations below.

Cincinnati Cinci./N. Kentucky
Cincinnati Cinci./N. Kentucky
From AED 532
Washington, D.C.
Washington, D.C.
From AED 545
Denver Intl
Denver Intl
From AED 645
Orlando
Orlando
From AED 789

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 220,657 searches.
Read reviews from past customers who have flown Emirates from Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Emirates
8.1
Very Good
3,428 reviews
Check prices

Overall

8.1

Crew

8.3

Entertainment

8.2

Boarding

8.1

Comfort

8.0

Food

7.9

Reviews

1 / 20
10.0
Excellent

Peter,Nov 2025

HKT - DXB

Great flight and the best food I’ve had on a plane
Emirates
8.1
Very Good
3,428 reviews
Emirates
8.1
Very Good
3,428 reviews
Check prices

Overall

8.1

Crew

8.3

Entertainment

8.2

Boarding

8.1

Comfort

8.0

Food

7.9

Reviews

1 / 20
10.0
Excellent

Peter,Nov 2025

HKT - DXB

Great flight and the best food I’ve had on a plane

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.
Direct flights from St. Louis

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 29 November 2025.

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

    The most selected flight destinations from Chicago for the current month are Atlanta, Mumbai, Boston. While Atlanta, Boston, Ahmedabad are the top choices made by travellers year-round.

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently November; 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?

    Check out the cheapest flights from Chicago to embark to:
    Travel from Chicago to Dubai from AED 1,991 round trip
    Travel from Chicago to Sharjah from AED 2,975 round trip
    Travel from Chicago to Dubai from AED 3,048 round trip

  • How does Cheapflights help users find flights from Chicago?

    900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

  • 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?

    Certainly. Search results for flights from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

    Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

See more FAQs

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?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight from Chicago today with Cheapflights!

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?

Certainly. Search results for flights from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and use a valid email address to enable the Price Alerts feature. That’s it!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.