AED 386+ Flights from Chicago | Cheapflights

What to know about flights from Chicago

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

Best flights from Chicago
Discover carefully curated flight deals from Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 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

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

Thu 11/917:45ORD - DXB

2 stops19h 50mAir France

Sat 20/900:40DXB - ORD

2 stops22h 30mAir France

Deal found 10/5AED 3,023

Wed 3/920:35ORD - DXB

Nonstop13h 35mEmirates

Mon 8/909:55DXB - ORD

Nonstop14h 50mEmirates

Deal found 9/5AED 3,045

Sat 11/1013:55ORD - AUH

Nonstop13h 25mEtihad Airways

Sat 25/1003:10AUH - ORD

Nonstop15h 05mEtihad Airways

Deal found 9/5AED 3,092

Wed 22/1015:50ORD - DXB

1 stop18h 55mAir Canada

Mon 27/1001:30DXB - ORD

2 stops22h 15mAir Canada

Deal found 10/5AED 3,114

Mon 11/812:30ORD - BKK

1 stop21h 15mKorean Air

Fri 29/809:50BKK - ORD

1 stop35h 50mKorean Air

Deal found 10/5AED 3,287

Direct flights from Chicago
Explore direct flight options from Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 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

Wed 3/920:35ORD - DXB

Nonstop13h 35mEmirates

Mon 8/909:55DXB - ORD

Nonstop14h 50mEmirates

Deal found 9/5AED 3,045

Sat 11/1013:55ORD - AUH

Nonstop13h 25mEtihad Airways

Sat 25/1003:10AUH - ORD

Nonstop15h 05mEtihad Airways

Deal found 9/5AED 3,092

Sun 10/811:10ORD - AMM

Nonstop12h 00mRoyal Jordanian

Sat 20/911:10AMM - ORD

Nonstop13h 00mRoyal Jordanian

Deal found 8/5AED 4,113

Last-minute flights from Chicago
Discover last-minute flight deals departing from Chicago. Data was last updated 10 May 2025 and is based on user searches.

Thu 15/508:45ORD - DXB

1 stop24h 50mMultiple Airlines

Sun 18/501:15DXB - ORD

1 stop23h 40mMultiple Airlines

Deal found 8/5AED 3,192

Thu 15/506:00ORD - BKK

2 stops34h 35mUnited Airlines

Sun 1/609:35BKK - ORD

2 stops34h 29mUnited Airlines

Deal found 8/5AED 3,302

Thu 15/508:50ORD - DXB

2 stops25h 55mAir Canada

Wed 21/500:50DXB - ORD

2 stops28h 22mAir Canada

Deal found 8/5AED 3,305

Thu 15/518:05ORD - DXB

2 stops43h 30mLufthansa

Sat 23/800:50DXB - ORD

1 stop21h 05mLufthansa

Deal found 10/5AED 3,820

Fri 16/509:23ORD - PUJ

Nonstop4h 42mUnited Airlines

Fri 23/513:50PUJ - ORD

Nonstop5h 05mUnited Airlines

Deal found 10/5AED 1,487

Fri 16/507:00ORD - DXB

2 stops31h 00mDelta

Tue 27/501:00DXB - ORD

1 stop22h 10mDelta

Deal found 10/5AED 2,927

Fri 16/511:10ORD - DXB

2 stops22h 25mUnited Airlines

Fri 23/501:55DXB - ORD

2 stops21h 38mUnited Airlines

Deal found 10/5AED 3,136

Sun 18/510:35MDW - DXB

2 stops27h 25mDelta

Wed 18/600:40DXB - MDW

2 stops27h 01mDelta

Deal found 9/5AED 3,140

Sun 18/519:20ORD - SHJ

1 stop16h 00mMultiple Airlines

Tue 10/618:55SHJ - ORD

2 stops34h 12mMultiple Airlines

Deal found 9/5AED 3,915

Mon 19/516:20ORD - DXB

1 stop21h 40mKLM

Wed 11/601:00DXB - ORD

1 stop22h 10mKLM

Deal found 9/5AED 3,236

Mon 19/507:15ORD - BKK

2 stops26h 30mDelta

Sun 1/602:35BKK - ORD

2 stops30h 45mDelta

Deal found 8/5AED 3,621

Mon 19/520:35ORD - DXB

Nonstop13h 35mEmirates

Wed 4/609:55DXB - ORD

Nonstop14h 50mEmirates

Deal found 9/5AED 3,937

One-way flights from Chicago
Search for one-way flight options from Chicago. Find affordable one-way fares based on user searches. Data last updated 10 May 2025.

Thu 14/809:23ORD - PUJ

Nonstop4h 42mUnited Airlines

Deal found 9/5AED 679

Sat 26/705:35ORD - PUJ

1 stop8h 16mDelta

Deal found 10/5AED 775

Fri 1/806:00ORD - PUJ

1 stop11h 06mJetBlue

Deal found 9/5AED 786

Sun 6/701:07ORD - PUJ

1 stop15h 30mCopa Airlines

Deal found 9/5AED 874

Mon 14/718:55ORD - PUJ

2 stops18h 50mSouthwest

Deal found 10/5AED 977

Thu 15/513:33ORD - DXB

2 stops30h 02mMultiple Airlines

Deal found 9/5AED 1,403

Sat 2/823:45ORD - DXB

1 stop17h 45mTurkish Airlines

Deal found 10/5AED 1,410

Sat 30/817:20ORD - DXB

2 stops20h 40mKLM

Deal found 9/5AED 1,447

Thu 11/920:10ORD - DXB

1 stop22h 55mRoyal Jordanian

Deal found 9/5AED 1,476

Fri 15/819:20ORD - DXB

1 stop16h 35mQatar Airways

Deal found 9/5AED 1,484

Sat 30/819:20ORD - SHJ

1 stop16h 00mQatar Airways

Deal found 9/5AED 1,524

Thu 14/813:55ORD - AMM

1 stop30h 50mEtihad Airways

Deal found 9/5AED 1,638

Find flights from Chicago within your budget

Fly to

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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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?

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.

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.

Oman Air

Oman Air

From AED 1,284

Emirates

Emirates

From AED 895

What are popular destinations to fly to from Chicago?

Some of the most frequent flights departing from Chicago everyday are: New York (1,655 flights per day), Detroit (1,202 flights per day), and Los Angeles (755 flights per day).

Houston Hobby

Houston Hobby

From AED 113

Washington, D.C.

Washington, D.C.

From AED 148

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

From AED 145

Kastrup Copenhagen

Kastrup Copenhagen

From AED 502

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Minneapolis St Paul, with prices starting at AED 215. Explore other affordable destinations below.

Minneapolis St Paul

Minneapolis St Paul

From AED 58

Houston Hobby

Houston Hobby

From AED 113

Toronto

Toronto

From AED 131

Cincinnati Cinci./N. Kentucky

Cincinnati Cinci./N. Kentucky

From AED 145

Airline reviews for flights from Chicago

Singapore Airlines

8.1

Very Good

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.

Singapore Airlines

8.1

Very Good

Singapore Airlines

8.1

Very Good

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

Singapore Airlines

8.1

Very Good

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

Singapore Airlines

8.1

Very Good

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.

7.8

Good

Singapore Airlines

8.1

Very Good

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.

7.5

Good

Singapore Airlines

8.1

Very Good

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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Related info for your journey

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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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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