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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 6/1. 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 343 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 29 November 2025.

Sun 8/208:45ORD - PUJ
1 stop8h 15mJetBlue
Thu 12/212:27PUJ - ORD
1 stop12h 43mJetBlue
Deal found 27/11AED 947
Thu 5/209:40ORD - PUJ
1 stop7h 27mJetBlue
Sat 14/214:07PUJ - ORD
1 stop11h 03mJetBlue
Deal found 27/11AED 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
Tue 3/312:37PUJ - ORD
1 stop12h 17mJetBlue
Deal found 28/11AED 999
Sat 28/206:04ORD - PUJ
1 stop11h 24mJetBlue
Mon 2/312:37PUJ - ORD
1 stop12h 17mJetBlue
Deal found 28/11AED 1,032
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 8/311:37PUJ - ORD
1 stop12h 19mJetBlue
Deal found 28/11AED 1,069
Mon 25/520:21ORD - PUJ
1 stop13h 12mJetBlue
Fri 29/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 28/11AED 1,091
Fri 1/520:21ORD - PUJ
1 stop12h 49mJetBlue
Tue 5/518:42PUJ - ORD
1 stop15h 03mJetBlue
Deal found 28/11AED 1,116
Wed 10/1207:00ORD - PUJ
1 stop7h 52mJetBlue
Sun 14/1213:00PUJ - ORD
1 stop10h 52mJetBlue
Deal found 28/11AED 1,120
Thu 18/1206:00ORD - PUJ
1 stop10h 15mJetBlue
Thu 25/1213:44PUJ - ORD
1 stop10h 20mJetBlue
Deal found 28/11AED 1,153
Wed 17/1207:00ORD - PUJ
1 stop7h 52mJetBlue
Fri 26/1213:44PUJ - ORD
1 stop10h 20mJetBlue
Deal found 28/11AED 1,190

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

Sat 28/2

06:04-19:28

1 stop11h 24m

Punta Cana

Wed 4/3

12:37-22:54

1 stop12h 17m

AED 947

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 28/2

06:04-19:28

1 stop11h 24m

Punta Cana

Sun 1/3

12:37-22:54

1 stop12h 17m

AED 1,069

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 14/12

05:00-16:50

1 stop9h 50m

Punta Cana

Thu 18/12

15:08-00:30

2 stops11h 22m

AED 1,267

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 17/2

06:04-19:45

1 stop11h 41m

Punta Cana

Tue 24/2

12:37-22:54

1 stop12h 17m

AED 1,271

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 18/12

06:00-16:30

1 stop8h 30m

Punta Cana

Sat 27/12

13:44-22:04

1 stop10h 20m

AED 1,271

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 24/2

08:45-15:17

Nonstop4h 32m

Punta Cana

Tue 3/3

16:25-19:38

Nonstop5h 13m

AED 1,289

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Thu 5/3

14:22-11:35

1 stop19h 13m

Punta Cana

Mon 9/3

13:48-01:04

1 stop12h 16m

AED 1,300

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 18/1

14:13-10:40

1 stop18h 27m

Punta Cana

Thu 22/1

15:05-00:24

1 stop11h 19m

AED 1,300

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 20/12

20:15-12:10

1 stop13h 55m

Punta Cana

Sat 27/12

13:44-22:04

1 stop10h 20m

AED 1,318

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Tue 17/3

08:47-14:19

Nonstop4h 32m

Punta Cana

Tue 24/3

11:56-20:35

1 stop9h 39m

AED 1,326

Flights are sorted by cheapest return flights first.

Deals found on 27/11

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 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 3,011
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: 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
New York
New York
From AED 337
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 New York, with prices starting at AED 337. Explore other affordable destinations below.

New York
New York
From AED 337
Orlando
Orlando
From AED 362
Cincinnati Cinci./N. Kentucky
Cincinnati Cinci./N. Kentucky
From AED 532
Washington, D.C.
Washington, D.C.
From AED 545

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
3,424 reviews
Check prices

Food

7.9

Comfort

8.0

Entertainment

8.2

Crew

8.3

Boarding

8.1

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
3,424 reviews
Emirates
8.1
Very Good
3,424 reviews
Check prices

Food

7.9

Comfort

8.0

Entertainment

8.2

Crew

8.3

Boarding

8.1

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 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 1,990 round trip
    Travel from Chicago to Sharjah from AED 2,997 round trip
    Travel from Chicago to Dubai from AED 3,221 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!

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