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AED 364+ 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 11/12. 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
22 Dec — 29 Dec1
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 22 November 2025.

Good round-trip deal

AED 546 or less

Good one-way deal

AED 532 or less
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 22 November 2025.

Sat 28/206:04ORD - PUJ
1 stop11h 24mJetBlue
Fri 6/312:37PUJ - ORD
1 stop12h 19mJetBlue
Deal found 21/11AED 947
Tue 2/1207:00ORD - PUJ
1 stop8h 21mJetBlue
Sat 6/1212:58PUJ - ORD
1 stop10h 54mJetBlue
Deal found 19/11AED 970
Tue 28/408:00ORD - PUJ
1 stop8h 45mJetBlue
Mon 4/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 19/11AED 992
Sun 7/1207:00ORD - PUJ
1 stop8h 21mJetBlue
Thu 11/1213:07PUJ - ORD
1 stop10h 45mJetBlue
Deal found 21/11AED 999
Wed 3/1207:00ORD - PUJ
1 stop7h 52mJetBlue
Thu 4/1213:00PUJ - ORD
1 stop10h 52mJetBlue
Deal found 21/11AED 1,021
Mon 23/206:04ORD - PUJ
1 stop7h 55mJetBlue
Sat 7/315:17PUJ - ORD
1 stop9h 39mJetBlue
Deal found 21/11AED 1,032
Mon 18/520:21ORD - PUJ
1 stop13h 12mJetBlue
Mon 25/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 20/11AED 1,050
Fri 12/1220:38ORD - PUJ
1 stop13h 24mJetBlue
Mon 15/1213:00PUJ - ORD
1 stop10h 52mJetBlue
Deal found 22/11AED 1,054
Wed 20/520:21ORD - PUJ
1 stop13h 12mJetBlue
Tue 26/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 21/11AED 1,069
Sun 14/1205:00ORD - PUJ
1 stop9h 50mSpirit Airlines
Thu 18/1218:08PUJ - ORD
1 stop8h 22mSpirit Airlines
Deal found 19/11AED 1,076
Fri 1/520:21ORD - PUJ
1 stop12h 49mJetBlue
Sun 10/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 19/11AED 1,083
Sun 17/508:40ORD - PUJ
1 stop7h 57mJetBlue
Fri 22/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 20/11AED 1,091

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 22 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 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 22/2

06:04-19:45

1 stop11h 41m

Punta Cana

Fri 27/2

15:39-22:54

1 stop9h 15m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 23/2

06:04-15:59

1 stop7h 55m

Punta Cana

Tue 10/3

11:37-22:56

1 stop12h 19m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Fri 20/2

06:04-15:59

1 stop7h 55m

Punta Cana

Sat 28/2

12:37-22:54

1 stop12h 17m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 22/12

06:45-18:15

1 stop9h 30m

Punta Cana

Mon 29/12

13:44-22:04

1 stop10h 20m

AED 947

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 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 8/2

08:45-19:00

1 stop8h 15m

Punta Cana

Sat 14/2

15:54-23:10

1 stop9h 16m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 23/2

06:04-19:45

1 stop11h 41m

Punta Cana

Mon 9/3

11:37-22:56

1 stop12h 19m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 8/2

08:45-19:00

1 stop8h 15m

Punta Cana

Fri 13/2

12:27-23:10

1 stop12h 43m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 21/2

06:04-19:45

1 stop11h 41m

Punta Cana

Thu 26/2

15:39-22:54

1 stop9h 15m

AED 970

Flights are sorted by cheapest return flights first.

Deals found on 21/11

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 Dubai. Price data was last updated on 14 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 3,011
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: New York (1,424 flights per day), Detroit (1,034 flights per day), and Atlanta (660 flights per day).

Washington, D.C.
Washington, D.C.
From AED 545
Amman Queen Alia Intl
Amman Queen Alia Intl
From AED 1,814
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From AED 3,121
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
Dallas/Fort Worth
Dallas/Fort Worth
From AED 546
Denver Intl
Denver Intl
From AED 645

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
3,423 reviews
Check prices

Boarding

8.1

Comfort

8.0

Food

7.9

Crew

8.3

Entertainment

8.2

Overall

8.1

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
3,423 reviews
Emirates
8.1
Very Good
3,423 reviews
Check prices

Boarding

8.1

Comfort

8.0

Food

7.9

Crew

8.3

Entertainment

8.2

Overall

8.1

Reviews

1 / 20
10.0
Excellent

Peter,Nov 2025

HKT - DXB

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

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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 22 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 are the cheapest airlines flying from Chicago to anywhere?

    Looking at our data, Royal Jordanian, Etihad Airways, and Emirates have been found to have the cheapest prices from Chicago. Here are some options available: Royal Jordanian flights from Chicago to Amman Queen Alia Intl (AED 2,353). Etihad Airways flights from Chicago to Abu Dhabi Zayed Intl (AED 2,935). Emirates flights from Chicago to Dubai Intl (AED 3,422).

  • 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 2,163 round trip
    Travel from Chicago to Sharjah from AED 3,030 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!

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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?

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!

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