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AED 386+ 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 1/7. 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
15 May — 22 May1
1 adult

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 10 May 2025.

Cheapest airline

Emirates

Good round-trip deal

AED 482 or less

Good one-way deal

AED 215 or less
On average, Emirates currently has the cheapest one-way flight from Chicago (avg. price of AED 5,370).
Price to beat on a round-trip flight from Chicago.
Price to beat on a one-way flight from Chicago.

Find flights from Chicago

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 10 May 2025.

Mon 11/809:23ORD - PUJ
Nonstop4h 42mUnited Airlines
Fri 15/813:50PUJ - ORD
Nonstop5h 05mUnited Airlines
Deal found 10/5AED 1,080
Sat 5/705:35ORD - PUJ
1 stop9h 12mDelta
Wed 9/714:52PUJ - ORD
1 stop10h 17mDelta
Deal found 8/5AED 1,230
Wed 6/801:07ORD - PUJ
1 stop11h 34mCopa Airlines
Thu 14/814:41PUJ - ORD
1 stop10h 41mCopa Airlines
Deal found 9/5AED 1,274
Wed 8/1006:00ORD - PUJ
1 stop10h 14mJetBlue
Tue 14/1011:30PUJ - ORD
1 stop10h 24mJetBlue
Deal found 9/5AED 1,623
Fri 12/919:50ORD - DXB
1 stop21h 40mTurkish Airlines
Wed 17/902:00DXB - ORD
1 stop24h 55mTurkish Airlines
Deal found 8/5AED 2,883
Tue 9/913:35ORD - DXB
2 stops24h 00mDelta
Mon 22/900:40DXB - ORD
2 stops25h 07mDelta
Deal found 9/5AED 2,887
Wed 22/1008:00ORD - DXB
2 stops41h 15mQatar Airways
Mon 27/1005:20DXB - ORD
1 stop19h 10mQatar Airways
Deal found 10/5AED 2,905
Wed 10/917:20ORD - DXB
2 stops20h 40mMultiple Airlines
Mon 22/900:40DXB - ORD
2 stops22h 30mMultiple Airlines
Deal found 9/5AED 2,923
Fri 12/917:59MDW - DXB
2 stops20h 01mDelta
Sun 21/900:40DXB - MDW
2 stops26h 56mDelta
Deal found 8/5AED 2,934
Wed 10/919:20ORD - SHJ
1 stop16h 00mQatar Airways
Mon 22/905:40SHJ - ORD
1 stop18h 25mQatar Airways
Deal found 8/5AED 2,949
Tue 5/819:20ORD - AUH
1 stop16h 55mQatar Airways
Tue 23/923:45AUH - ORD
1 stop24h 20mQatar Airways
Deal found 9/5AED 2,993
Thu 11/917:45ORD - DXB
2 stops19h 50mAir France
Sat 20/900:40DXB - ORD
2 stops22h 30mAir France
Deal found 10/5AED 3,023

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 10 May 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

Mon 11/8

09:23-15:05

Nonstop4h 42m

Punta Cana

Fri 15/8

13:50-17:55

Nonstop5h 05m

AED 1,080

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sat 5/7

05:35-15:47

1 stop9h 12m

Punta Cana

Wed 9/7

14:52-00:09

1 stop10h 17m

AED 1,230

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 6/8

01:07-13:41

1 stop11h 34m

Punta Cana

Thu 14/8

14:41-00:22

1 stop10h 41m

AED 1,274

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Wed 8/10

06:00-17:14

1 stop10h 14m

Punta Cana

Tue 14/10

11:30-20:54

1 stop10h 24m

AED 1,623

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Fri 12/9

19:50-02:30

1 stop21h 40m

Dubai Intl

Wed 17/9

02:00-17:55

1 stop24h 55m

AED 2,883

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Tue 9/9

13:35-22:35

2 stops24h 00m

Dubai Intl

Mon 22/9

00:40-16:47

2 stops25h 07m

AED 2,887

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Wed 22/10

08:00-10:15

2 stops41h 15m

Dubai Intl

Mon 27/10

05:20-15:30

1 stop19h 10m

AED 2,905

ChicagoDubai

ORD - DXB

ORDDXB

Chicago O'Hare Intl

Wed 10/9

17:20-23:00

2 stops20h 40m

Dubai Intl

Mon 22/9

00:40-14:10

2 stops22h 30m

AED 2,923

ChicagoDubai

MDW - DXB

MDWDXB

Chicago Midway

Fri 12/9

17:59-23:00

2 stops20h 01m

Dubai Intl

Sun 21/9

00:40-18:36

2 stops26h 56m

AED 2,934

ChicagoSharjah

ORD - SHJ

ORDSHJ

Chicago O'Hare Intl

Wed 10/9

19:20-20:20

1 stop16h 00m

Sharjah

Mon 22/9

05:40-15:05

1 stop18h 25m

AED 2,949

Flights are sorted by cheapest return flights first.

Deals found on 9/5

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 9 May 2025.

To ensure you get the cheapest price possible for a flight from Chicago, you should look to book at least 57 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, February is the cheapest month in which you can book a flight from Chicago (average of AED 2,178). Flying from Chicago in June will prove the most costly (average of AED 3,507). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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.

Entertainment

8.0

Boarding

8.2

Crew

8.6

Overall

8.1

Food

7.7

Comfort

7.9

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Entertainment

8.0

Boarding

8.2

Crew

8.6

Overall

8.1

Food

7.7

Comfort

7.9

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Entertainment

8.0

Boarding

8.2

Crew

8.6

Overall

8.1

Food

7.7

Comfort

7.9

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.
8.0
Very Good

Entertainment

8.0

Boarding

8.2

Crew

8.6

Overall

8.1

Food

7.7

Comfort

7.9

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Entertainment

8.0

Boarding

8.2

Crew

8.6

Overall

8.1

Food

7.7

Comfort

7.9

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

Entertainment

8.0

Boarding

8.2

Crew

8.6

Overall

8.1

Food

7.7

Comfort

7.9

Reviews

1 / 20
6.0
Good

Pierre,Apr 2025

MLE - SIN

3 boarding pass checkpoints at the gate. Long line before boarding. Poor leg room in economy.. Flight crew rounds practically non existent during flight.

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Direct flights from Illinois

Book a direct flight from one of these other cities located in Illinois.

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 10 May 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, Boston, Athens. While Atlanta, Boston, Mumbai 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 February; 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 2,273 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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